Standard Article

The Intramolecular Michael Reaction

  1. R. Daniel Little,
  2. Mohammad R. Masjedizadeh,
  3. Olof Wallquist‡,¶,
  4. Jim I. Mcloughlin§,‖

Published Online: 15 OCT 2004

DOI: 10.1002/0471264180.or047.02

Organic Reactions

Organic Reactions

How to Cite

Little, R. D., Masjedizadeh, M. R., Wallquist, O. and Mcloughlin, J. I. 2004. The Intramolecular Michael Reaction. Organic Reactions. 47:2:315–552.

Author Information

  1. University of California, Department of Chemistry, Santa Barbara, California

  1. Syntex, Palo Alto, California

  2. Ciba-Geigy, Fribourg, France

  3. §

    St. Louis, Missouri

  1. (In Part)

  2. (In Part)

Publication History

  1. Published Online: 15 OCT 2004

Chemistry Terms

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Abstract

Like its intermolecular counterpart, the intramolecular Michael reaction involves the addition of a nucleophile, often referred to as the donor, to an acceptor, usually an olefin bearing one or more functional groups capable of stabilizing a carbanion.

Strictly speaking, the term Michael reaction refers to the 1,4-, or conjugate, addition of a carbanion to an acceptor under basic conditions. However, just as the scope of a previous review dealing with the Michael reaction was expanded to encompass a wide range of acceptors and noncarbon-centered donors, so too has the scope of this chapter. Furthermore, reactions occurring under both basic and acidic conditions are discussed.

As suggested by the name, the intramolecular Michael reaction most often leads to the formation of a ring, either carbo- or heterocyclic. However, there are many examples of sequential, or tandem, Michael reactions wherein the first inter- or intramolecular Michael reaction is followed directly by an intramolecular variant leading to the formation of more than one ring. In other instances, a nucleophile is delivered to the β-carbon atom of an acceptor in a process which does not lead to the production of a ring. These transformations are referred to as heteroconjugate addition reactions.

In contrast to the intermolecular counterpart, the intramolecular Michael reaction has been formally reviewed only once. Two contemporary publications, however, have focused on the reaction and serve to highlight recent developments. The first example dates back to 1898 when Guthzeit reported that on standing at room temperature for a year, or upon treatment with a “small amount” of pyridine, ethyl α-carboxyglutaconate transforms to the “bimeric” ester. Subsequent reinvestigation by Ingold and co-workers led to the revised structure and to the suggestion that it arose via an initial inter- followed by an intramolecular Michael reaction.

The first systematic study of the intramolecular Michael reaction appeared in 1945. Thus, treatment of a variety of substituted ethyl coumarinates with sodium alkoxide in alcohol solvent leads to coumarins. Of particular interest is the fact that the reaction proceeds efficiently even when the β carbon of the acceptor is substituted with two sterically demanding groups. This apparent lack of retardation by double substitution at the β carbon contrasts sharply with the intermolecular Michael reaction and appears to be general. Another example highlighting the susceptibility of sterically hindered systems to participate in intra- but not intermolecular Michael reactions comes from studies concerning the mode of activation of the antibiotics calicheamicin and esperamicin.

Access to the tetracyclic precursor of a taxol analog was achieved via an intramolecular Michael addition to the relatively hindered β carbon of enone.

The intramolecular Michael reaction again formed the subject of publications appearing in 1951, 1957, and 1962. During the 1960s, comparatively little study or use of the reaction was reported. A notable and historically significant exception, however, was Corey's use of it in a total synthesis of longifolene.

This approach to the construction of tricyclic systems is similar to that suggested mechanistically in the base-induced conversion of santonin to santonic acid.

The 1970s and 1980s witnessed a dramatic increase in uses of the intramolecular Michael reaction. Much of the chemistry discussed in this chapter focuses upon material discovered during this time period.

Keywords:

  • intramolecular Michael reaction;
  • mechanism;
  • stereoelectronic control;
  • scope;
  • limitations;
  • retro reactions;
  • sequential reactions;
  • Lewis acid promoted cyclizations;
  • method comparisons;
  • oxygen donor;
  • nitrogen donor;
  • carbon donor;
  • acceptors;
  • silyl enol ethers;
  • allylic silanes;
  • propargylic silanes;
  • Diels-Alder reaction;
  • experimental procedure;
  • chelation control;
  • aldol condensation

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Compound Information
Molecular Weight:0
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:362.44
Molecular Formula:C19H22O5S
InChIKey:VXVHJLDRWGTSRH-ZNOIYHFQSA-N
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Compound Information
Molecular Weight:234.337
Molecular Formula:C12H10OS2
InChIKey:IETMKYFYBRQFCW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:304.791
Molecular Formula:C16H13ClO2S
InChIKey:APXLLXOUEUEHJU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:53.491
Molecular Formula:ClH4N
InChIKey:NLXLAEXVIDQMFP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:284.398
Molecular Formula:C12H16N2O2S2
InChIKey:RQUMDIKMCVRCPC-CMDGGOBGSA-N
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Compound Information
Molecular Weight:144.1699
Molecular Formula:C10H8O
InChIKey:UPEUQDJSUFHFQP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:616.628
Molecular Formula:C29H23F3N2O6S2
InChIKey:CHQSBYVCFUCUNQ-WARYPIAISA-N
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Compound Information
Molecular Weight:337.257
Molecular Formula:C9H8BrNO2S3
InChIKey:GXXUTBMMNDVNIH-UHFFFAOYSA-M
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Compound Information
Molecular Weight:285.425
Molecular Formula:C14H24N2O2S
InChIKey:OYXGQDNCJJRTSP-RMKNXTFCSA-O
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Molecular Weight:366.477
Molecular Formula:C21H22N2O2S
InChIKey:OKVOCMPVDOXIJJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:216.2326
Molecular Formula:C13H12O3
InChIKey:VRERWPQACJDHPG-XBLVEGMJSA-N
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Compound Information
Molecular Weight:339.236
Molecular Formula:C16H12Cl2O2S
InChIKey:NCFIQYDGSIYCCK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:340.434
Molecular Formula:C17H24O5S
InChIKey:YDECUTZOTARDFW-SQWLQELKSA-N
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Compound Information
Molecular Weight:332.374
Molecular Formula:C16H16N2O4S
InChIKey:ULOBRLBNGMRQHH-UMVBOHGHSA-N
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Compound Information
Molecular Weight:468.562
Molecular Formula:C26H28O6S
InChIKey:VWFOOKXKTGJLFY-MFKUBSTISA-N
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Compound Information
Molecular Weight:230.284
Molecular Formula:C9H14N2O3S
InChIKey:JNQZOQVPPSOHIP-MYINAIGISA-N
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Compound Information
Molecular Weight:270.371
Molecular Formula:C11H14N2O2S2
InChIKey:ZCPSCZAGHCBZFU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:76.121
Molecular Formula:CH4N2S
InChIKey:UMGDCJDMYOKAJW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:248.364
Molecular Formula:C13H12OS2
InChIKey:RDCYYRIAXVYGNO-FLIBITNWSA-N
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Compound Information
Molecular Weight:322.424
Molecular Formula:C19H18N2OS
InChIKey:SFTQGBOYGNUIJY-WMHBUWLTSA-N
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Compound Information
Molecular Weight:304.816
Molecular Formula:C11H13ClN2O2S2
InChIKey:FQURUKDGRGWVNE-BQYQJAHWSA-N
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Compound Information
Molecular Weight:217.308
Molecular Formula:C9H16N2O2S
InChIKey:SIVRZHGDTZKSNQ-VOTSOKGWSA-O
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Compound Information
Molecular Weight:174.261
Molecular Formula:C8H14O2S
InChIKey:NERHVQNYOCSIAQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:183.228
Molecular Formula:C8H9NO2S
InChIKey:SHPHBMZZXHFXDF-VOTSOKGWSA-N
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Compound Information
Molecular Weight:108.1378
Molecular Formula:C7H8O
InChIKey:UNELZWLTCBQRGC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:78.133
Molecular Formula:C2H6OS
InChIKey:IAZDPXIOMUYVGZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:438.496
Molecular Formula:C23H22N2O5S
InChIKey:MLTJDPPNQLEBMP-KCZVDYSFSA-N
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Compound Information
Molecular Weight:154.185
Molecular Formula:C4H10O4S
InChIKey:DENRZWYUOJLTMF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:304.791
Molecular Formula:C16H13ClO2S
InChIKey:JOMKZYVGKDTELZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:258.361
Molecular Formula:C9H9NO2S3
InChIKey:HQQVPKWVLIOVQN-UHFFFAOYSA-M
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Compound Information
Molecular Weight:362.44
Molecular Formula:C19H22O5S
InChIKey:ZUMAHEMTCCUPCJ-LDADJPATSA-N
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Compound Information
Molecular Weight:174.261
Molecular Formula:C8H14O2S
InChIKey:CZWCBSFIITVHPZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:516.587
Molecular Formula:C24H24N2O7S2
InChIKey:WFMXWKCRQGHUCN-LPPMMHEWSA-N
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Compound Information
Molecular Weight:101.19
Molecular Formula:C6H15N
InChIKey:ZMANZCXQSJIPKH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:290.79
Molecular Formula:C10H11ClN2O2S2
InChIKey:MJWYVZHXMNIXLZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:256.344
Molecular Formula:C10H12N2O2S2
InChIKey:DOBTYTTXHNXBPW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:304.816
Molecular Formula:C11H13ClN2O2S2
InChIKey:MJOXKLYCBHJDIB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:270.371
Molecular Formula:C11H14N2O2S2
InChIKey:ORCXKLWMKBSCCI-CMDGGOBGSA-N
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Compound Information
Molecular Weight:217.308
Molecular Formula:C9H16N2O2S
InChIKey:XBWAQEINOIVVLK-GQCTYLIASA-O
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Compound Information
Molecular Weight:298.399
Molecular Formula:C18H18O2S
InChIKey:RAOZFXPRHNIGGR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:217.673
Molecular Formula:C8H8ClNO2S
InChIKey:WDNJYXIESUMYHL-AATRIKPKSA-N
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Compound Information
Molecular Weight:279.377
Molecular Formula:C14H18N2O2S
InChIKey:NNSKETULUGVDPR-BQYQJAHWSA-O
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Compound Information
Molecular Weight:157.07
Molecular Formula:C6H6Se
InChIKey:Not Available
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Compound Information
Molecular Weight:335.241
Molecular Formula:C10H11BrN2O2S2
InChIKey:HMFSUCZPLFRSDH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:265.351
Molecular Formula:C13H16N2O2S
InChIKey:LPQIRZRSHOPMLF-BQYQJAHWSA-O
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Compound Information
Molecular Weight:294.409
Molecular Formula:C16H22O3S
InChIKey:SLBMXVICVLTGQT-YEOLMYPVSA-N
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Compound Information
Molecular Weight:214.324
Molecular Formula:C11H18O2S
InChIKey:BYAZGCMENWNGKO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:336.489
Molecular Formula:C19H28O3S
InChIKey:ZBYIESINRHFTIJ-PEJOBZMASA-N
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Compound Information
Molecular Weight:280.383
Molecular Formula:C15H20O3S
InChIKey:MHUFUYOTLWOPRV-BLVKFPJESA-N
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Compound Information
Molecular Weight:346.441
Molecular Formula:C19H22O4S
InChIKey:WBFHAGKVFZFLKF-VDZJLULYSA-N
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Compound Information
Molecular Weight:328.813
Molecular Formula:C18H13ClO2S
InChIKey:ZXPPGMRJDFWANV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:402.504
Molecular Formula:C22H26O5S
InChIKey:AEUPLPYRFGGOIC-RBISFHTESA-N
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Compound Information
Molecular Weight:444.584
Molecular Formula:C25H32O5S
InChIKey:OCJSNQKUCHTNCY-UGDMGKLASA-N
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Compound Information
Molecular Weight:73.0938
Molecular Formula:C3H7NO
InChIKey:ZMXDDKWLCZADIW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:304.816
Molecular Formula:C11H13ClN2O2S2
InChIKey:FONWVBUWECPMRZ-BQYQJAHWSA-N
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Compound Information
Molecular Weight:56.1056
Molecular Formula:HKO
InChIKey:KWYUFKZDYYNOTN-UHFFFAOYSA-M
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Compound Information
Molecular Weight:344.469
Molecular Formula:C23H20OS
InChIKey:BIEPIIAMVODHON-UHFFFAOYSA-N
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Compound Information
Molecular Weight:273.395
Molecular Formula:C10H11NO2S3
InChIKey:RENRPJMWRZZHPG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:389.329
Molecular Formula:C18H13BrOS2
InChIKey:HZCXRFABXCSACB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:298.424
Molecular Formula:C13H18N2O2S2
InChIKey:YRAMRMVKTWADMG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:318.818
Molecular Formula:C17H15ClO2S
InChIKey:HCKXCDZBGYFFJC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:310.433
Molecular Formula:C18H14OS2
InChIKey:HVLRBSYOCNXFSY-BOPFTXTBSA-N
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Compound Information
Molecular Weight:158.1965
Molecular Formula:C11H10O
InChIKey:XAJIQJSLJKBJTP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:188.287
Molecular Formula:C9H16O2S
InChIKey:ODHKPLLJDFHROJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:160.234
Molecular Formula:C7H12O2S
InChIKey:SAAOGNSLESCZGT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:310.433
Molecular Formula:C18H14OS2
InChIKey:QOVORVYWQXNVBY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:360.401
Molecular Formula:C20H24O6
InChIKey:WEKVFSMLTGEWPX-NTYZMLGYSA-N
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Compound Information
Molecular Weight:302.388
Molecular Formula:C17H18O3S
InChIKey:NTPAHBKUIUMKKR-RRQGHBQHSA-N
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Compound Information
Molecular Weight:239.334
Molecular Formula:C12H17NO2S
InChIKey:CNUUQBYXPCTKGX-VAGKLZBCSA-N
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Compound Information
Molecular Weight:373.681
Molecular Formula:C16H11Cl3O2S
InChIKey:AOLFLLXGSOIRPX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:76.141
Molecular Formula:CS2
InChIKey:QGJOPFRUJISHPQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:262.124
Molecular Formula:C8H8BrNO2S
InChIKey:XJSMEIJFAVKWIT-AATRIKPKSA-N
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Compound Information
Molecular Weight:454.534
Molecular Formula:C22H30O8S
InChIKey:GGMGJEWVNPKTGX-YPWDBRJWSA-N
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Compound Information
Molecular Weight:160.234
Molecular Formula:C7H12O2S
InChIKey:YBBUVCQXWYEIRC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:236.33
Molecular Formula:C13H16O2S
InChIKey:LELXTZLWZMXAAT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:37.954
Molecular Formula:AlH4Li
InChIKey:OCZDCIYGECBNKL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:136.0796
Molecular Formula:C2H9NaO5
InChIKey:AYRVGWHSXIMRAB-UHFFFAOYSA-M
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Compound Information
Molecular Weight:324.462
Molecular Formula:C15H20N2O2S2
InChIKey:YJCASHTWWJDEMT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:132.1146
Molecular Formula:C5H8O4
InChIKey:BEPAFCGSDWSTEL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:224.342
Molecular Formula:C11H12OS2
InChIKey:LAPQTXIOMJMVJU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:336.489
Molecular Formula:C19H28O3S
InChIKey:LWRBKFDQQSLEOG-KKXDTOCCSA-N
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Compound Information
Molecular Weight:146.207
Molecular Formula:C6H10O2S
InChIKey:YNFYCBDMMKUYKX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:136.315
Molecular Formula:Cl2Zn
InChIKey:Not Available
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Compound Information
Molecular Weight:298.424
Molecular Formula:C13H18N2O2S2
InChIKey:PPEGETXXWHBSOW-PKNBQFBNSA-N
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Compound Information
Molecular Weight:346.441
Molecular Formula:C19H22O4S
InChIKey:FBGQMDJUPYFWFI-LPRJTOQXSA-N
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Compound Information
Molecular Weight:317.358
Molecular Formula:C13H19NO6S
InChIKey:BANROEHLXLZKSE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:307.84
Molecular Formula:C10H10ClNO2S3
InChIKey:XCBWZIAGKALLKV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:334.817
Molecular Formula:C17H15ClO3S
InChIKey:SYXMSKPEXDORSH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:248.364
Molecular Formula:C13H12OS2
InChIKey:ITBYIGWFYKEXNK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:350.515
Molecular Formula:C20H30O3S
InChIKey:CDXNLSDKSNPULX-JVPBZIDWSA-N
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Compound Information
Molecular Weight:39.9971
Molecular Formula:HNaO
InChIKey:HEMHJVSKTPXQMS-UHFFFAOYSA-M
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Compound Information
Molecular Weight:18.0153
Molecular Formula:H2O
InChIKey:XLYOFNOQVPJJNP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:464.436
Molecular Formula:C17H15F3N2O6S2
InChIKey:XPJSIQZUGYDKMT-JXBCQSMISA-N
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Compound Information
Molecular Weight:420.4529
Molecular Formula:C22H28O8
InChIKey:DLMXYRJUZFVYSI-MAFWIJBESA-N
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Compound Information
Molecular Weight:302.388
Molecular Formula:C17H18O3S
InChIKey:GEXVVNZHJXPOBC-GHRIWEEISA-N
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Compound Information
Molecular Weight:240.319
Molecular Formula:C12H16O3S
InChIKey:KZMBYGBFWLBGJT-JFGNBEQYSA-N
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Compound Information
Molecular Weight:271.333
Molecular Formula:C12H17NO4S
InChIKey:LJBVIZUHMWXXOW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:484.566
Molecular Formula:C28H24N2O4S
InChIKey:ICMDOZOAMAVPEP-FKCDAAJZSA-N
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Compound Information
Molecular Weight:270.371
Molecular Formula:C11H14N2O2S2
InChIKey:CAJOIGBNEHBCSV-BQYQJAHWSA-N
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Compound Information
Molecular Weight:172.202
Molecular Formula:C7H8O3S
InChIKey:JOXIMZWYDAKGHI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:420.519
Molecular Formula:C22H28O6S
InChIKey:IUQPTCPZGOTUQV-WVRJOINRSA-N
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Compound Information
Molecular Weight:245.361
Molecular Formula:C11H20N2O2S
InChIKey:MNAPDIFQRDABKG-AATRIKPKSA-O
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Compound Information
Molecular Weight:292.806
Molecular Formula:C9H8ClNO2S3
InChIKey:TVXHSJNADGTVEL-UHFFFAOYSA-M
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Compound Information
Molecular Weight:85.1475
Molecular Formula:C5H11N
InChIKey:Not Available
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Compound Information
Molecular Weight:287.421
Molecular Formula:C11H13NO2S3
InChIKey:SRXCHEWPXQHECQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:282.4
Molecular Formula:C18H18OS
InChIKey:AWPQVIKLETXMPM-MORSLUCNSA-N
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Compound Information
Molecular Weight:245.361
Molecular Formula:C11H20N2O2S
InChIKey:HGAYAHCEVXQVGZ-SOFGYWHQSA-O
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Compound Information
Molecular Weight:272.387
Molecular Formula:C10H11NO2S3
InChIKey:MHXRHFKLYGRQLU-UHFFFAOYSA-M
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Compound Information
Molecular Weight:22.98976928
Molecular Formula:HNa
InChIKey:MPMYQQHEHYDOCL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:335.241
Molecular Formula:C10H11BrN2O2S2
InChIKey:CZSTVWPTHPMIOA-VOTSOKGWSA-N
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Compound Information
Molecular Weight:248.319
Molecular Formula:C18H16O
InChIKey:VZXBHDUKADILLK-SQIWNDBBSA-N
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Compound Information
Molecular Weight:216.257
Molecular Formula:C8H12N2O3S
InChIKey:KGUPIRNHNWZFIM-UUEMRFSQSA-N
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Compound Information
Molecular Weight:334.817
Molecular Formula:C17H15ClO3S
InChIKey:ZCLXWCCAHNOSGN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:114.551
Molecular Formula:CH3ClO2S
InChIKey:QARBMVPHQWIHKH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:349.267
Molecular Formula:C11H13BrN2O2S2
InChIKey:HEKWSDJFTKKSEB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:259.388
Molecular Formula:C12H22N2O2S
InChIKey:CSJGMANLPKDNBU-AATRIKPKSA-O
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Compound Information
Molecular Weight:138.2055
Molecular Formula:CK2O3
InChIKey:BWHMMNNQKKPAPP-UHFFFAOYSA-L
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Compound Information
Molecular Weight:285.31
Molecular Formula:C13H18SSe
InChIKey:YAPPCCTXSCXSGO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:274.335
Molecular Formula:C15H14O3S
InChIKey:IRILMZKVTHKOSD-RRFJBIMHSA-N
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Compound Information
Molecular Weight:290.79
Molecular Formula:C10H11ClN2O2S2
InChIKey:JJRFQVWDLQFFMY-VOTSOKGWSA-N
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Compound Information
Molecular Weight:256.344
Molecular Formula:C10H12N2O2S2
InChIKey:WVPMFRKIUCXURX-BQYQJAHWSA-N
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Compound Information
Molecular Weight:126.132
Molecular Formula:C2H6O4S
InChIKey:VAYGXNSJCAHWJZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:86.1754
Molecular Formula:C6H14
InChIKey:VLKZOEOYAKHREP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:95.211
Molecular Formula:Cl2Mg
InChIKey:TWRXJAOTZQYOKJ-UHFFFAOYSA-L
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Compound Information
Molecular Weight:339.236
Molecular Formula:C16H12Cl2O2S
InChIKey:MGNUXJOBUOCQBL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:349.267
Molecular Formula:C11H13BrN2O2S2
InChIKey:HNCLKWXEAYDTKL-BQYQJAHWSA-N
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Compound Information
Molecular Weight:287.421
Molecular Formula:C11H13NO2S3
InChIKey:CNYQHDSEQAURSF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:310.3884
Molecular Formula:C23H18O
InChIKey:FNRMLJQMDQDTIW-WUKNDPDISA-N
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Compound Information
Molecular Weight:314.356
Molecular Formula:C17H14O4S
InChIKey:ZNCXJAGPBPXNGU-FTRCILSKSA-N
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Compound Information
Molecular Weight:112.212
Molecular Formula:C4H9KO
InChIKey:LPNYRYFBWFDTMA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:268.372
Molecular Formula:C14H20O3S
InChIKey:DEHUSUUZDLFEFY-NTEUORMPSA-N
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Compound Information
Molecular Weight:271.333
Molecular Formula:C12H17NO4S
InChIKey:DJWAABRLDZVGMV-HSIUBREASA-N
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Compound Information
Molecular Weight:324.462
Molecular Formula:C15H20N2O2S2
InChIKey:CBEAEBFBVPUGMQ-VAWYXSNFSA-N
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Compound Information
Molecular Weight:318.818
Molecular Formula:C17H15ClO2S
InChIKey:DWBWVRMRIWDNDZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:298.399
Molecular Formula:C18H18O2S
InChIKey:AWRAGPNRYAIJEJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:270.371
Molecular Formula:C11H14N2O2S2
InChIKey:LBNYQGNKZWLZJF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:185.243
Molecular Formula:C8H11NO2S
InChIKey:PZFLATCPEJSIMF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:328.813
Molecular Formula:C18H13ClO2S
InChIKey:GKGHJIGCSGBWJZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:186.2497
Molecular Formula:C13H14O
InChIKey:OGKKCSAGHUIPND-CMDGGOBGSA-N
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Compound Information
Molecular Weight:340.434
Molecular Formula:C17H24O5S
InChIKey:IGABTPRSGAPQHR-CRKCGEKBSA-N
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Compound Information
Molecular Weight:231.335
Molecular Formula:C10H18N2O2S
InChIKey:BDVLCICCLMPAOT-FNORWQNLSA-O
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Compound Information
Molecular Weight:318.818
Molecular Formula:C17H15ClO2S
InChIKey:VVVJEZDSUJMETA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:197.254
Molecular Formula:C9H11NO2S
InChIKey:BATSYPGXFHOMJB-VOTSOKGWSA-N
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Compound Information
Molecular Weight:234.337
Molecular Formula:C12H10OS2
InChIKey:DHFAGGXMBJSCHU-XFFZJAGNSA-N
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Compound Information
Molecular Weight:240.319
Molecular Formula:C12H16O3S
InChIKey:UQFSTDCKIHSGJJ-QDEBKDIKSA-N
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Compound Information
Molecular Weight:294.409
Molecular Formula:C16H22O3S
InChIKey:QSFGXJCCOPZAAR-FQEVSTJZSA-N
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Compound Information
Molecular Weight:72.1057
Molecular Formula:C4H8O
InChIKey:WYURNTSHIVDZCO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:142.219
Molecular Formula:C7H10OS
InChIKey:WRKYCQOFEBORNV-KNVOCYPGSA-N
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Compound Information
Molecular Weight:302.388
Molecular Formula:C17H18O3S
InChIKey:VUSLGXSBVNDYCZ-RSSMCMFDSA-N
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Compound Information
Molecular Weight:32.0419
Molecular Formula:CH4O
InChIKey:OKKJLVBELUTLKV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:271.5
Molecular Formula:Cl2Hg
InChIKey:Not Available
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Compound Information
Molecular Weight:383.687
Molecular Formula:C16H12BrClO2S
InChIKey:WTWJQUZXEQWOTM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:318.818
Molecular Formula:C17H15ClO2S
InChIKey:MUKFZQHDZCVKFG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:389.329
Molecular Formula:C18H13BrOS2
InChIKey:PIFPKIYRWIHTEI-YVLHZVERSA-N
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Compound Information
Molecular Weight:280.383
Molecular Formula:C15H20O3S
InChIKey:WBKAXLABWBWQFC-HHEAZKOWSA-N
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Compound Information
Molecular Weight:410.465
Molecular Formula:C17H18N2O6S2
InChIKey:KTQCDCJWVRYPKG-VBEUMERESA-N
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Compound Information
Molecular Weight:34.081
Molecular Formula:H2S
InChIKey:RWSOTUBLDIXVET-UHFFFAOYSA-N
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Compound Information
Molecular Weight:346.441
Molecular Formula:C19H22O4S
InChIKey:QNQCEWGFIRXURV-XDHOZWIPSA-N
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Compound Information
Molecular Weight:304.816
Molecular Formula:C11H13ClN2O2S2
InChIKey:FDOPVONXMGZSKL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:39.0983
Molecular Formula:HK
InChIKey:NTTOTNSKUYCDAV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:167.2481
Molecular Formula:C10H17NO
InChIKey:NDKBVBUGCNGSJJ-UHFFFAOYSA-M
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:383.687
Molecular Formula:C16H12BrClO2S
InChIKey:DXTLQJCSXHZWHL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:222.303
Molecular Formula:C12H14O2S
InChIKey:UJPMLHANVRXQAA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:290.79
Molecular Formula:C10H11ClN2O2S2
InChIKey:MDNVMTBANCLYNN-VOTSOKGWSA-N
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Compound Information
Molecular Weight:72.171
Molecular Formula:HKS
InChIKey:ZOCLAPYLSUCOGI-UHFFFAOYSA-M
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Compound Information
Molecular Weight:46.0684
Molecular Formula:C2H6O
InChIKey:LFQSCWFLJHTTHZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:346.441
Molecular Formula:C19H22O4S
InChIKey:OYGIYJVWHFEACO-AYOQOUSVSA-N
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Compound Information
Molecular Weight:84.933
Molecular Formula:CH2Cl2
InChIKey:YMWUJEATGCHHMB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:302.388
Molecular Formula:C17H18O3S
InChIKey:IOMGZZABTAOZAZ-XYPHTWIQSA-N
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Compound Information
Molecular Weight:284.398
Molecular Formula:C12H16N2O2S2
InChIKey:ILNZFUVOVLMUSR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:220.331
Molecular Formula:C13H16OS
InChIKey:INEXSFKPSHXRHP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:468.562
Molecular Formula:C26H28O6S
InChIKey:LOHSKFQMKSYQEA-BYXVTNLJSA-N
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Compound Information
Molecular Weight:36.461
Molecular Formula:ClH
InChIKey:VEXZGXHMUGYJMC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:444.584
Molecular Formula:C25H32O5S
InChIKey:RDWXRLIBBAVRIP-QEBZRKRVSA-N
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Compound Information
Molecular Weight:74.1216
Molecular Formula:C4H10O
InChIKey:DKGAVHZHDRPRBM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:294.409
Molecular Formula:C16H22O3S
InChIKey:JHRCOBDIWZIOCT-QINHECLXSA-N
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Compound Information
Molecular Weight:218.638
Molecular Formula:C8H11ClN2O3
InChIKey:BDGVDLIAIQNIRV-RXMQYKEDSA-N
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Compound Information
Molecular Weight:294.409
Molecular Formula:C16H22O3S
InChIKey:GFBUBJFTOLKMPQ-RBZFPXEDSA-N
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Compound Information
Molecular Weight:225.217
Molecular Formula:Br2Zn
InChIKey:VNDYJBBGRKZCSX-UHFFFAOYSA-L
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Compound Information
Molecular Weight:190.262
Molecular Formula:C11H10OS
InChIKey:DSOGSTMUZHTXLS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:232.664
Molecular Formula:C9H13ClN2O3
InChIKey:LNXYTDACAVHJLJ-ZCFIWIBFSA-N
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Compound Information
Molecular Weight:290.79
Molecular Formula:C10H11ClN2O2S2
InChIKey:VQVMBVKWTPAVNF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:251.302
Molecular Formula:C12H13NO3S
InChIKey:ZDYVRSLAEXCVBX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:373.681
Molecular Formula:C16H11Cl3O2S
InChIKey:YCGYJMHJKLXUEU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:100.459
Molecular Formula:ClHO4
InChIKey:VLTRZXGMWDSKGL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:216.297
Molecular Formula:C10H16O3S
InChIKey:OBVHPOJQQIKKNT-FNORWQNLSA-N
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Compound Information
Molecular Weight:394.482
Molecular Formula:C20H26O6S
InChIKey:ZWXPOPCKPHGULK-FOVRIMIMSA-N
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Compound Information
Molecular Weight:79.0999
Molecular Formula:C5H5N
InChIKey:Not Available
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Compound Information
Molecular Weight:290.79
Molecular Formula:C10H11ClN2O2S2
InChIKey:SLDGWAYNEFFYNI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:299.386
Molecular Formula:C14H21NO4S
InChIKey:CHLXINRJNKRODY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:299.386
Molecular Formula:C14H21NO4S
InChIKey:GISPYFIQKAGVSX-SPDZDTJJSA-N
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Compound Information
Molecular Weight:268.372
Molecular Formula:C14H20O3S
InChIKey:WFPYSBFYUNUHES-BNOWGMLFSA-N
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Compound Information
Molecular Weight:290.79
Molecular Formula:C10H11ClN2O2S2
InChIKey:XWVHWCNMQWIAJG-AATRIKPKSA-N
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Compound Information
Molecular Weight:239.334
Molecular Formula:C12H17NO2S
InChIKey:XDLJOGFKEVIGPJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:90.121
Molecular Formula:C4H10O2
InChIKey:XTHFKEDIFFGKHM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:248.319
Molecular Formula:C18H16O
InChIKey:VZXBHDUKADILLK-FSALDASDSA-N
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Compound Information
Molecular Weight:282.4
Molecular Formula:C18H18OS
InChIKey:AWPQVIKLETXMPM-KKXDTOCCSA-N
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Compound Information
Molecular Weight:80.1277
Molecular Formula:C6H8
InChIKey:UVJHQYIOXKWHFD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:336.489
Molecular Formula:C19H28O3S
InChIKey:ZBYIESINRHFTIJ-SRVCANOKSA-N
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Compound Information
Molecular Weight:280.383
Molecular Formula:C15H20O3S
InChIKey:WBKAXLABWBWQFC-IBWPGLOJSA-N
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Compound Information
Molecular Weight:280.383
Molecular Formula:C15H20O3S
InChIKey:WBKAXLABWBWQFC-CTYUOQFJSA-N
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Compound Information
Molecular Weight:280.383
Molecular Formula:C15H20O3S
InChIKey:WBKAXLABWBWQFC-NMLBAAHISA-N
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Compound Information
Molecular Weight:280.383
Molecular Formula:C15H20O3S
InChIKey:WBKAXLABWBWQFC-MOMAJJCNSA-N
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Compound Information
Molecular Weight:280.383
Molecular Formula:C15H20O3S
InChIKey:WBKAXLABWBWQFC-JUIVLLAYSA-N
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Compound Information
Molecular Weight:280.383
Molecular Formula:C15H20O3S
InChIKey:MHUFUYOTLWOPRV-CWTRNNRKSA-N
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Compound Information
Molecular Weight:280.383
Molecular Formula:C15H20O3S
InChIKey:WBKAXLABWBWQFC-NFWAQSGPSA-N
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Compound Information
Molecular Weight:280.383
Molecular Formula:C15H20O3S
InChIKey:WBKAXLABWBWQFC-QEPJRFBGSA-N
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Compound Information
Molecular Weight:294.409
Molecular Formula:C16H22O3S
InChIKey:JHRCOBDIWZIOCT-GUXCAODWSA-N
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Compound Information
Molecular Weight:294.409
Molecular Formula:C16H22O3S
InChIKey:GFBUBJFTOLKMPQ-XCLFUZPHSA-N
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Compound Information
Molecular Weight:294.409
Molecular Formula:C16H22O3S
InChIKey:SLBMXVICVLTGQT-NEVJAFOQSA-N
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Compound Information
Molecular Weight:444.584
Molecular Formula:C25H32O5S
InChIKey:RDWXRLIBBAVRIP-JIIBJNMISA-N
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Compound Information
Molecular Weight:240.319
Molecular Formula:C12H16O3S
InChIKey:KZMBYGBFWLBGJT-CKYFFXLPSA-N
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Compound Information
Molecular Weight:346.441
Molecular Formula:C19H22O4S
InChIKey:OYGIYJVWHFEACO-ATZDWAIDSA-N
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Compound Information
Molecular Weight:346.441
Molecular Formula:C19H22O4S
InChIKey:WBFHAGKVFZFLKF-HHXXYDBFSA-N
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Compound Information
Molecular Weight:268.372
Molecular Formula:C14H20O3S
InChIKey:WFPYSBFYUNUHES-MRVWCRGKSA-N
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Compound Information
Molecular Weight:340.434
Molecular Formula:C17H24O5S
InChIKey:YDECUTZOTARDFW-IIAWOOMASA-N
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Compound Information
Molecular Weight:302.388
Molecular Formula:C17H18O3S
InChIKey:IOMGZZABTAOZAZ-KBRIMQKVSA-N
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Compound Information
Molecular Weight:302.388
Molecular Formula:C17H18O3S
InChIKey:NTPAHBKUIUMKKR-XOKHGSTOSA-N
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Compound Information
Molecular Weight:468.562
Molecular Formula:C26H28O6S
InChIKey:LOHSKFQMKSYQEA-RMUDUWAUSA-N
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Compound Information
Molecular Weight:206.2808
Molecular Formula:C13H18O2
InChIKey:DVLVRIPHUHMQFW-LYIQGSDWSA-N
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Compound Information
Molecular Weight:119.378
Molecular Formula:CHCl3
InChIKey:HEDRZPFGACZZDS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:486.49
Molecular Formula:C21H26O11S
InChIKey:UAKZSJSSWXJTFU-XKRYSZRTSA-N
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Compound Information
Molecular Weight:362.44
Molecular Formula:C19H22O5S
InChIKey:VXVHJLDRWGTSRH-UPRAQXHNSA-N
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Compound Information
Molecular Weight:250.2903
Molecular Formula:C14H18O4
InChIKey:CXEBYQZRRLLCBV-ICIURTGMSA-N
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Compound Information
Molecular Weight:180.2005
Molecular Formula:C10H12O3
InChIKey:RJDCEKUQZIHGKD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:170.2057
Molecular Formula:C9H14O3
InChIKey:AOQGITSLLXGPOQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:232.3181
Molecular Formula:C15H20O2
InChIKey:OKKCRTQMTGCTKN-LALPHHSUSA-N
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Compound Information
Molecular Weight:234.334
Molecular Formula:C15H22O2
InChIKey:GJLUHNVBUKKWGJ-FTBWOMCISA-N
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Compound Information
Molecular Weight:344.38
Molecular Formula:C15H20O7S
InChIKey:KHDRPZSSJJSKRT-WYWSWGBSSA-N
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Compound Information
Molecular Weight:130.1418
Molecular Formula:C6H10O3
InChIKey:XYIBRDXRRQCHLP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:236.3068
Molecular Formula:C14H20O3
InChIKey:IALHXHBUWGEVCQ-IQTUOKKGSA-N
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Compound Information
Molecular Weight:198.3019
Molecular Formula:C12H22O2
InChIKey:HCVKZKHQIVPCJE-FNORWQNLSA-N
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Compound Information
Molecular Weight:304.4546
Molecular Formula:C14H28O5Si
InChIKey:UGDAWNFPDKPXKC-YZTHKRDXSA-N
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Compound Information
Molecular Weight:218.2915
Molecular Formula:C14H18O2
InChIKey:SKWKSKHWZFBUIN-VOTSOKGWSA-N
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Compound Information
Molecular Weight:206.2808
Molecular Formula:C13H18O2
InChIKey:HWQHXSNNCXFJFO-ZWNOBZJWSA-N
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Compound Information
Molecular Weight:734.9808
Molecular Formula:C42H46O8Si2
InChIKey:GSXMHMIZIKDZDF-QGDVVULKSA-N
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Compound Information
Molecular Weight:192.9665
Molecular Formula:H6O8P2
InChIKey:QVLTXCYWHPZMCA-UHFFFAOYSA-K
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Compound Information
Molecular Weight:302.388
Molecular Formula:C17H18O3S
InChIKey:SWEAQNYITDLZPR-COXVUDFISA-N
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Compound Information
Molecular Weight:346.568
Molecular Formula:C19H38O3S
InChIKey:BOWJUTCWCFDEFR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:31.9988
Molecular Formula:O2
InChIKey:MYMOFIZGZYHOMD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:236.3068
Molecular Formula:C14H20O3
InChIKey:PTGMAJIVPNEBOV-IGQOVBAYSA-N
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Compound Information
Molecular Weight:90.0349
Molecular Formula:C2H2O4
InChIKey:MUBZPKHOEPUJKR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:428.453
Molecular Formula:C19H24O9S
InChIKey:LCAHQYMZXVRSBE-OWYHZJEWSA-N
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Compound Information
Molecular Weight:208.2106
Molecular Formula:C11H12O4
InChIKey:CBTSFKXPZHGRAI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:198.3019
Molecular Formula:C12H22O2
InChIKey:DEVKHTOCKWDIRD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:330.506
Molecular Formula:C16H26O3S2
InChIKey:AKHZYWJKXCMGIK-RXTYADHFSA-N
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