Standard Article

Reductions with Samarium(II) Iodide

  1. Gary A. Molander

Published Online: 15 OCT 2004

DOI: 10.1002/0471264180.or046.03

Organic Reactions

Organic Reactions

How to Cite

Molander, G. A. 2004. Reductions with Samarium(II) Iodide. Organic Reactions. 46:3:211–367.

Author Information

  1. University of Colorado at Boulder, Department of Chemistry and Biochemistry, Boulder, Colorado

Publication History

  1. Published Online: 15 OCT 2004

Chemistry Terms

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Abstract

Reducing agents (along with complementary oxidants) constitute the most fundamental class of reagents available to synthetic chemists for the conversion of organic substrates to desirable organic products. As a consequence of their central importance, the search for novel reducing agents remains the focus of intense exploration. Especially valued are those reagents that not only transform a broad range of diverse functional groups, but do so with a high degree of selectivity. Since the early 1980s, samarium(II) iodide (SmI2) has been increasingly recognized as a reducing agent capable of meeting the intensifying demands of synthetic organic chemistry. Although the compound itself has been known for many years, it was not until Kagan and co-workers developed a convenient synthesis of SmI2 and outlined its general reactivity with common organic functional groups that SmI2 became of general interest and importance to synthetic organic chemists.

Samarium(II) iodide is a powerful one-electron reducing agent that can be prepared in moderate concentrations (0.1 M) in tetrahydrofuran (THF) by one of several different reactions from samarium metal.

Deep blue solutions of SmI2 are generated in virtually quantitative yields by these procedures, but the preparations using diiodomethane or diiodoethane as the oxidants would appear to be the easiest and most reliable methods. The reducing agent can be stored as a solution in THF for reasonably long periods of time, particularly when it is stabilized by a small amount of samarium metal. Alternatively, the solvent may be removed, providing SmI2(THF)n powder. For synthetic purposes, SmI2 is typically generated and utilized in situ, although THF solutions of SmI2 are commercially available.

The reduction potential of Sm+2/Sm+3 as measured in water is −1.55 V. However, the reduction potential as well as the ability of SmI2 to promote the reduction of diverse organic substrates varies widely according to the solvent and the presence of various additives.

Kagan's pioneering studies on the reaction of SmI2 with organic substrates not only provided a general outline for its reactivity, but also inspired an extraordinary number of subsequent studies with important ramifications for selective organic synthesis. As a consequence of these extensive studies, SmI2 has emerged as one of the more useful reducing agents in synthetic organic chemistry. The complementary reactivity of SmI2 as compared to the vast inventory of other available reducing agents constitutes one reason for its appeal. Another attraction of SmI2 is its ready accessibility, either from commercial sources or by in situ preparation via one of the convenient methods outlined above. The high chemoselectivity exhibited by SmI2 and the ability to change its reactivity (selectivity) rather dramatically based upon solvent effects further enhance its attractiveness. Finally, SmI2 is easily handled by standard techniques for the manipulation of air-sensitive materials.

This chapter outlines some of the practical aspects of reactions employing SmI2, but is strictly limited to functional group reductions. Thus those reactions promoted by SmI2 that result in the formation of new carbon–carbon bonds are not included. The chapter is organized according to the type of organic functional groups involved, and topics covered include the reduction of organic halides, sulfonates, and sulfones, reductive elimination/fragmentation processes; reduction of aldehydes and ketones; reduction of carboxylic acids and their derivatives; reduction of conjugated carbonyl substrates; reductive cleavage of α-heterosubstituted carbonyl substrates; reduction of cyclopropyl ketones; various deoxygenation reactions; reduction of nitrogen-based functional groups; and finally an outline of the reduction of miscellaneous functional groups that cannot be appropriately assigned to the general classifications outlined above. In covering these topics, the literature has been surveyed through 1992.

Keywords:

  • reductions;
  • samarium iodide;
  • mechanisms;
  • organic halides;
  • sulfonates;
  • sulfones;
  • aldehydes;
  • ketones;
  • carboxylic acids;
  • conjugated carbonyl substrates;
  • heterosubstituted carbonyl compounds;
  • cyclopropyl ketones;
  • nitrogen-based functional groups;
  • reductive cleavage;
  • functional groups;
  • scope;
  • limitation;
  • method comparison;
  • experimental procedures

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Compound Information
Molecular Weight:152.621
Molecular Formula:C9H9Cl
InChIKey:IWTYTFSSTWXZFU-QPJJXVBHSA-N
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Compound Information
Molecular Weight:324.437
Molecular Formula:C20H20O2S
InChIKey:WXYOJZHNWOWKHT-IZAXUBKRSA-N
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Compound Information
Molecular Weight:165.1461
Molecular Formula:C8H7NO3
InChIKey:HUSYTLMIRXITQS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:200.3178
Molecular Formula:C12H24O2
InChIKey:FTYSFPPFCAOKDQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:138.2499
Molecular Formula:C10H18
InChIKey:IYLIJOSJWHXAEF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:233.104
Molecular Formula:C12H9Br
InChIKey:PKJBWOWQJHHAHG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:135.2062
Molecular Formula:C9H13N
InChIKey:LYUQWQRTDLVQGA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:86.1323
Molecular Formula:C5H10O
InChIKey:Not Available
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Compound Information
Molecular Weight:270.005
Molecular Formula:C8H14Br2
InChIKey:PHBMJDSRZYQBPS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:118.088
Molecular Formula:C4H6O4
InChIKey:KDYFGRWQOYBRFD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:468.605
Molecular Formula:C27H32O5S
InChIKey:JQNGBBHRGFKVGO-XLKYERIQSA-N
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Compound Information
Molecular Weight:88.1051
Molecular Formula:C4H8O2
InChIKey:KQNPFQTWMSNSAP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:120.1485
Molecular Formula:C8H8O
InChIKey:KWOLFJPFCHCOCG-UHFFFAOYSA-N
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Molecular Weight:116.1583
Molecular Formula:C6H12O2
InChIKey:SKCYVGUCBRYGTE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:152.2334
Molecular Formula:C10H16O
InChIKey:SXHFWQXLKHFKKJ-SREVYHEPSA-N
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Compound Information
Molecular Weight:196.286
Molecular Formula:C12H20O2
InChIKey:ICFXAAQORMYPDE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:267.989
Molecular Formula:C8H12Br2
InChIKey:RRGUVJJVBAZCFI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:199.045
Molecular Formula:C8H7BrO
InChIKey:LIGACIXOYTUXAW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:502.338
Molecular Formula:C30H22FeO4
InChIKey:CFRGFUXOGXIURO-AGIYBIRKSA-L
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Compound Information
Molecular Weight:279.171
Molecular Formula:C11H19BrO3
InChIKey:NLEJOVBTXCGBBF-RXKWGBCNSA-N
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Compound Information
Molecular Weight:454.7275
Molecular Formula:C31H50O2
InChIKey:WAPKZPLWLMQRHV-SNDLGPCHSA-N
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Compound Information
Molecular Weight:156.566
Molecular Formula:C7H5ClO2
InChIKey:XRHGYUZYPHTUJZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:102.1317
Molecular Formula:C5H10O2
InChIKey:Not Available
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Compound Information
Molecular Weight:405.099
Molecular Formula:C27H45Cl
InChIKey:OTVRYZXVVMZHHW-UQEKCUHDSA-N
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Compound Information
Molecular Weight:93.1265
Molecular Formula:C6H7N
InChIKey:BSKHPKMHTQYZBB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:282.4183
Molecular Formula:C17H30O3
InChIKey:JBMQPNQJXGCCDX-FYWRMAATSA-N
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Compound Information
Molecular Weight:196.2445
Molecular Formula:C14H12O
InChIKey:OTKCEEWUXHVZQI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:296.1883
Molecular Formula:C11H21IO
InChIKey:RQNNUWBVUWYEGT-JGZJWPJOSA-N
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Compound Information
Molecular Weight:197.2325
Molecular Formula:C13H11NO
InChIKey:DCNUQRBLZWSGAV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:107.557
Molecular Formula:C4H7ClO
InChIKey:Not Available
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Compound Information
Molecular Weight:168.2328
Molecular Formula:C10H16O2
InChIKey:ZUMGBVSYIVKLDH-QHHAFSJGSA-N
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Compound Information
Molecular Weight:148.1586
Molecular Formula:C9H8O2
InChIKey:WBYWAXJHAXSJNI-VOTSOKGWSA-N
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Compound Information
Molecular Weight:234.3355
Molecular Formula:C18H18
InChIKey:OOPCIDOIJKFFKD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:295.258
Molecular Formula:C16H23Br
InChIKey:HDXSUJKNDQLPNH-PEZBUJJGSA-N
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Compound Information
Molecular Weight:197.2325
Molecular Formula:C13H11NO
InChIKey:ZVSKZLHKADLHSD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:216.188
Molecular Formula:C9H12O6
InChIKey:BDBGJSXZKMTMGP-UXTLFEIASA-N
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Compound Information
Molecular Weight:120.1485
Molecular Formula:C8H8O
InChIKey:FXLOVSHXALFLKQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:160.2108
Molecular Formula:C8H16O3
InChIKey:MRYSSTRVUMCKKB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:398.518
Molecular Formula:C22H26N2O3S
InChIKey:BRZLMPJUCYVLRC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:249.231
Molecular Formula:C12H25Br
InChIKey:Not Available
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Compound Information
Molecular Weight:200.2747
Molecular Formula:C11H20O3
InChIKey:HDBRIBPPNQGSMG-GMCFVEKCSA-N
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Compound Information
Molecular Weight:112.1696
Molecular Formula:C7H12O
InChIKey:JHKUFOOWUVOJDX-SNAWJCMRSA-N
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Compound Information
Molecular Weight:314.5356
Molecular Formula:C17H34O3Si
InChIKey:UJMLVJZFVFLECB-BYNSBNAKSA-N
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Compound Information
Molecular Weight:265.3496
Molecular Formula:C18H19NO
InChIKey:CRNGAKQBKWKJRM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:180.2866
Molecular Formula:C12H20O
InChIKey:CHOKIAHSAHEPPA-HJWRWDBZSA-N
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Compound Information
Molecular Weight:198.3019
Molecular Formula:C12H22O2
InChIKey:FCGGFZBPKGCPCR-ZYHUDNBSSA-N
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Compound Information
Molecular Weight:396.503
Molecular Formula:C22H24N2O3S
InChIKey:HGGHVTQWIUGBIA-WYMLVPIESA-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:112.1696
Molecular Formula:C7H12O
InChIKey:UJBOOUHRTQVGRU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:182.3025
Molecular Formula:C12H22O
InChIKey:OSVWDMYHJIEODC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:132.588
Molecular Formula:C6H9ClO
InChIKey:XZXKNCHQEUKAHN-PHDIDXHHSA-N
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Compound Information
Molecular Weight:140.567
Molecular Formula:C7H5ClO
InChIKey:PASDCCFISLVPSO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:185.061
Molecular Formula:C8H9Br
InChIKey:QXISTPDUYKNPLU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:140.1797
Molecular Formula:C8H12O2
InChIKey:KXPWRCPEMHIZGU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:136.1512
Molecular Formula:C7H8N2O
InChIKey:WARCRYXKINZHGQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:206.1932
Molecular Formula:C8H14O6
InChIKey:YSAVZVORKRDODB-PHDIDXHHSA-N
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Compound Information
Molecular Weight:220.2213
Molecular Formula:C12H12O4
InChIKey:PWXJQQZGGNDORF-UMNHJUIQSA-N
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Compound Information
Molecular Weight:332.479
Molecular Formula:C15H24O4S2
InChIKey:SSPISBWXCTYVRF-PHIMTYICSA-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:183.045
Molecular Formula:C8H7Br
InChIKey:YMOONIIMQBGTDU-VOTSOKGWSA-N
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Compound Information
Molecular Weight:98.143
Molecular Formula:C6H10O
InChIKey:SAXBDVYNGGCITG-ONEGZZNKSA-N
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Compound Information
Molecular Weight:416.5088
Molecular Formula:C27H28O4
InChIKey:MXYLLYBWXIUMIT-PFBJBMPXSA-N
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Compound Information
Molecular Weight:102.1317
Molecular Formula:C5H10O2
InChIKey:UUIQMZJEGPQKFD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:150.1745
Molecular Formula:C9H10O2
InChIKey:CRZQGDNQQAALAY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:142.2817
Molecular Formula:C10H22
InChIKey:DIOQZVSQGTUSAI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:418.613
Molecular Formula:C23H30O3S2
InChIKey:ILKMQIZLEDKOPR-KTZCYXFVSA-N
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Compound Information
Molecular Weight:162.616
Molecular Formula:C10H7Cl
InChIKey:JTPNRXUCIXHOKM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:606.016
Molecular Formula:C27H47Cl3O8
InChIKey:OMXCJQPNPCOOCQ-YXFYBALFSA-N
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Compound Information
Molecular Weight:370.465
Molecular Formula:C20H22N2O3S
InChIKey:KHSBWYIYRBEOAG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:270.709
Molecular Formula:C13H15ClO4
InChIKey:FDRWFICSFOLXJM-URIFGBQESA-N
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Compound Information
Molecular Weight:100.1589
Molecular Formula:C6H12O
InChIKey:UFLHIIWVXFIJGU-ONEGZZNKSA-N
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Compound Information
Molecular Weight:144.1684
Molecular Formula:C7H12O3
InChIKey:FNENWZWNOPCZGK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:123.1094
Molecular Formula:C6H5NO2
InChIKey:SIOXPEMLGUPBBT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:116.1616
Molecular Formula:C5H12N2O
InChIKey:AVQQQNCBBIEMEU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:267.3654
Molecular Formula:C18H21NO
InChIKey:RKBKYUOXBCOVSZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:532.715
Molecular Formula:C36H40N2O2
InChIKey:XZICMCMRHVSUNR-KYJUHHDHSA-N
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Compound Information
Molecular Weight:190.2814
Molecular Formula:C13H18O
InChIKey:QZJXYOGAZYAYDK-JTQLQIEISA-N
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Compound Information
Molecular Weight:72.1057
Molecular Formula:C4H8O
InChIKey:ZEXFAVZTIZXHFA-ONEGZZNKSA-N
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Compound Information
Molecular Weight:411.199
Molecular Formula:C14H19BrO9
InChIKey:CYAYKKUWALRRPA-RGDJUOJXSA-N
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Compound Information
Molecular Weight:132.1577
Molecular Formula:C6H12O3
InChIKey:GFUIDHWFLMPAGY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:132.588
Molecular Formula:C6H9ClO
InChIKey:CCHNWURRBFGQCD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:229.071
Molecular Formula:C9H9BrO2
InChIKey:LQEQVVBJQZOHHD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:108.1809
Molecular Formula:C8H12
InChIKey:Not Available
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Compound Information
Molecular Weight:126.583
Molecular Formula:C7H7Cl
InChIKey:KCXMKQUNVWSEMD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:214.3013
Molecular Formula:C12H22O3
InChIKey:DJUQSEODGOJFMO-UKKRHICBSA-N
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Compound Information
Molecular Weight:142.583
Molecular Formula:C7H7ClO
InChIKey:ZSRDNPVYGSFUMD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:137.136
Molecular Formula:C7H7NO2
InChIKey:SKZKKFZAGNVIMN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:414.5806
Molecular Formula:C32H30
InChIKey:NNYNOQVWBSLEAX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:116.1583
Molecular Formula:C6H12O2
InChIKey:Not Available
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Compound Information
Molecular Weight:210.657
Molecular Formula:C11H11ClO2
InChIKey:MKAVFMMBKPWPHE-QUYIPOCNSA-N
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Compound Information
Molecular Weight:294.2155
Molecular Formula:C12H23I
InChIKey:FXQHFVJEECQKAU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:102.1748
Molecular Formula:C6H14O
InChIKey:ZSIAUFGUXNUGDI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:296.4067
Molecular Formula:C19H24N2O
InChIKey:CHMMZOATTBEOAL-YJBOKZPZSA-N
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Compound Information
Molecular Weight:162.2283
Molecular Formula:C11H14O
InChIKey:YWMCLNQNOQDQHB-DUXPYHPUSA-N
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Compound Information
Molecular Weight:20.0276
Molecular Formula:H2O
InChIKey:Not Available
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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:148.631
Molecular Formula:C7H13ClO
InChIKey:OZYHIICGFXIVAU-BQBZGAKWSA-N
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Compound Information
Molecular Weight:328.4452
Molecular Formula:C21H28O3
InChIKey:FMNPCVNWRFPDCA-MJCUULBUSA-N
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Compound Information
Molecular Weight:116.2013
Molecular Formula:C7H16O
InChIKey:BBMCTIGTTCKYKF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:108.1378
Molecular Formula:C7H8O
InChIKey:RDOXTESZEPMUJZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:135.1632
Molecular Formula:C8H9NO
InChIKey:XXUNIGZDNWWYED-UHFFFAOYSA-N
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Compound Information
Molecular Weight:200.1886
Molecular Formula:C9H12O5
InChIKey:YKKJYSDODXHPRR-PXBUCIJWSA-N
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Compound Information
Molecular Weight:321.3682
Molecular Formula:C17H23NO5
InChIKey:YGQUWMOKRXRYDZ-KNPMLCFXSA-N
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Compound Information
Molecular Weight:170.2918
Molecular Formula:C11H22O
InChIKey:MYZLGYHAZXJDMC-ONGXEEELSA-N
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Compound Information
Molecular Weight:142.1956
Molecular Formula:C8H14O2
InChIKey:HOWBPXBYCPKWBL-GQCTYLIASA-N
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Compound Information
Molecular Weight:96.1271
Molecular Formula:C6H8O
InChIKey:BRPYKGUPEIEWRQ-ONEGZZNKSA-N
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Compound Information
Molecular Weight:156.566
Molecular Formula:C7H5ClO2
InChIKey:IKCLCGXPQILATA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:106.1219
Molecular Formula:C7H6O
InChIKey:HUMNYLRZRPPJDN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:22.964
Molecular Formula:H2LiN
InChIKey:AFRJJFRNGGLMDW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:226.335
Molecular Formula:C12H18O2S
InChIKey:SHDAAKLJJRFBCI-VHSXEESVSA-N
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Compound Information
Molecular Weight:440.595
Molecular Formula:C26H32O4S
InChIKey:JTFPJLXOQOIERB-PUHDZGQXSA-N
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Compound Information
Molecular Weight:216.3618
Molecular Formula:C16H24
InChIKey:QWYVTJQFFVAOFP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:108.1378
Molecular Formula:C7H8O
InChIKey:WVDDGKGOMKODPV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:93.1265
Molecular Formula:C6H7N
InChIKey:FKNQCJSGGFJEIZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:136.1479
Molecular Formula:C8H8O2
InChIKey:QPJVMBTYPHYUOC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:194.2701
Molecular Formula:C12H18O2
InChIKey:ULGNWXBAOUCUOS-CMDGGOBGSA-N
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Compound Information
Molecular Weight:168.2759
Molecular Formula:C11H20O
InChIKey:VSGHQMVSHALPID-VIFPVBQESA-N
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Compound Information
Molecular Weight:286.4085
Molecular Formula:C19H26O2
InChIKey:ULAADVBNYHGIBP-GFEQUFNTSA-N
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Compound Information
Molecular Weight:142.1956
Molecular Formula:C8H14O2
InChIKey:ZQWPRMPSCMSAJU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:277.155
Molecular Formula:C11H17BrO3
InChIKey:XPHMWOIYGZERNR-AATRIKPKSA-N
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Compound Information
Molecular Weight:234.3355
Molecular Formula:C18H18
InChIKey:GXBNHFMSIXKWHZ-YDWXAUTNSA-N
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Compound Information
Molecular Weight:135.1632
Molecular Formula:C8H9NO
InChIKey:LSBDFXRDZJMBSC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:354.4825
Molecular Formula:C23H30O3
InChIKey:ACNFVLCLXXAFSU-XNBWIAOKSA-N
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Compound Information
Molecular Weight:494.642
Molecular Formula:C29H34O5S
InChIKey:JANAPGYOUYRYOC-VUTJFYCQSA-N
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Compound Information
Molecular Weight:176.727
Molecular Formula:C10H21Cl
InChIKey:ZTEHOZMYMCEYRM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:128.212
Molecular Formula:C8H16O
InChIKey:ZPVFWPFBNIEHGJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:121.584
Molecular Formula:C5H9ClO
InChIKey:Not Available
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Compound Information
Molecular Weight:279.3761
Molecular Formula:C19H21NO
InChIKey:VMBVAJFCIGJIGI-HQYXKAPLSA-N
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Compound Information
Molecular Weight:138.2499
Molecular Formula:C10H18
InChIKey:HRAGAKKBZWYBSJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:121.1796
Molecular Formula:C8H11N
InChIKey:BHHGXPLMPWCGHP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:279.171
Molecular Formula:C11H19BrO3
InChIKey:DDTOQJZLKVBRJO-JQCXWYLXSA-N
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Compound Information
Molecular Weight:296.2314
Molecular Formula:C12H25I
InChIKey:GCDPERPXPREHJF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:62.0678
Molecular Formula:C2H6O2
InChIKey:Not Available
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Compound Information
Molecular Weight:492.626
Molecular Formula:C29H32O5S
InChIKey:PIYGGYGMVZBHBD-VUTJFYCQSA-N
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Compound Information
Molecular Weight:206.2824
Molecular Formula:C16H14
InChIKey:GILVKAZLLFNSHJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:170.2487
Molecular Formula:C10H18O2
InChIKey:VZHUBBUZNIULNM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:346.442
Molecular Formula:C22H18O2S
InChIKey:UXBRMSHTEPIPIZ-VSKRKVRLSA-N
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Compound Information
Molecular Weight:156.2652
Molecular Formula:C10H20O
InChIKey:Not Available
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Compound Information
Molecular Weight:298.058
Molecular Formula:C10H18Br2
InChIKey:Not Available
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Compound Information
Molecular Weight:293.197
Molecular Formula:C12H21BrO3
InChIKey:LUHPMMQMQHDCOV-SGIHWFKDSA-N
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Compound Information
Molecular Weight:154.2493
Molecular Formula:C10H18O
InChIKey:YKFKEYKJGVSEIX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:162.657
Molecular Formula:C8H15ClO
InChIKey:MAYXLOUFYYYNEI-JGVFFNPUSA-N
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Compound Information
Molecular Weight:37.975
Molecular Formula:CH3LiO
InChIKey:JILPJDVXYVTZDQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:190.1938
Molecular Formula:C8H14O5
InChIKey:VKNUORWMCINMRB-ZCFIWIBFSA-N
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Compound Information
Molecular Weight:116.2046
Molecular Formula:C6H16N2
InChIKey:KWYHDKDOAIKMQN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:245.156
Molecular Formula:C11H17BrO
InChIKey:RPQVJULHMCWCDG-FNCVBFRFSA-N
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Compound Information
Molecular Weight:100.1589
Molecular Formula:C6H12O
InChIKey:Not Available
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Compound Information
Molecular Weight:154.2078
Molecular Formula:C12H10
InChIKey:ZUOUZKKEUPVFJK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:136.1479
Molecular Formula:C8H8O2
InChIKey:WLJVXDMOQOGPHL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:374.154
Molecular Formula:C16H22Br2
InChIKey:WTCDLYTZYDYMFD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:444.602
Molecular Formula:C24H44O7
InChIKey:NKFDWZXNEFBOOS-FZNHKMOLSA-N
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Compound Information
Molecular Weight:155.582
Molecular Formula:C7H6ClNO
InChIKey:RBGDLYUEXLWQBZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:204.2665
Molecular Formula:C16H12
InChIKey:IVQVTOPMNKVTPP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:204.78
Molecular Formula:C12H25Cl
InChIKey:YAYNEUUHHLGGAH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:130.2312
Molecular Formula:C7H18N2
InChIKey:DMQSHEKGGUOYJS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:156.566
Molecular Formula:C7H5ClO2
InChIKey:LULAYUGMBFYYEX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:148.1586
Molecular Formula:C9H8O2
InChIKey:ONPJWQSDZCGSQM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:348.437
Molecular Formula:C11H7Cl5O2
InChIKey:SRXWJNIJUNUUSC-JFMZLQSISA-N
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Compound Information
Molecular Weight:352.4666
Molecular Formula:C23H28O3
InChIKey:PCFMKOMEBNTPNG-VROINQGHSA-N
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Compound Information
Molecular Weight:116.1583
Molecular Formula:C6H12O2
InChIKey:WDAXFOBOLVPGLV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:134.1751
Molecular Formula:C9H10O
InChIKey:YGCZTXZTJXYWCO-UHFFFAOYSA-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:130.2279
Molecular Formula:C8H18O
InChIKey:KBPLFHHGFOOTCA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:108.642
Molecular Formula:C3H9ClSi
InChIKey:IJOOHPMOJXWVHK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:207.067
Molecular Formula:C10H7Br
InChIKey:DLKQHBOKULLWDQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:316.4776
Molecular Formula:C21H32O2
InChIKey:CIBOOPKLBBFHSW-HXZOEFROSA-N
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Compound Information
Molecular Weight:140.567
Molecular Formula:C7H5ClO
InChIKey:AVPYQKSLYISFPO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:136.1479
Molecular Formula:C8H8O2
InChIKey:ZWLPBLYKEWSWPD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:178.2277
Molecular Formula:C11H14O2
InChIKey:JAGZUIGGHGTFHO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:214.3459
Molecular Formula:C16H22
InChIKey:JPWJCYLWZFYUBK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:156.2652
Molecular Formula:C10H20O
InChIKey:PDNDYBJRFPLDPP-BDAKNGLRSA-N
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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:296.1453
Molecular Formula:C10H17IO2
InChIKey:NMCCXHHYVXADOI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:78.1118
Molecular Formula:C6H6
InChIKey:UHOVQNZJYSORNB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:123.1094
Molecular Formula:C6H5NO2
InChIKey:Not Available
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Compound Information
Molecular Weight:248.746
Molecular Formula:C12H21ClO3
InChIKey:MBDHVQOZDHBXNJ-SGIHWFKDSA-N
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Compound Information
Molecular Weight:99.1311
Molecular Formula:C5H9NO
InChIKey:SECXISVLQFMRJM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:393.432
Molecular Formula:C17H33BrO3Si
InChIKey:UPBQFBKTVJQQSD-REWJHTLYSA-N
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Compound Information
Molecular Weight:206.668
Molecular Formula:C12H11ClO
InChIKey:OMBYDGFZHZTLHQ-RYUDHWBXSA-N
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Compound Information
Molecular Weight:231.13
Molecular Formula:C10H15BrO
InChIKey:NJQADTYRAYFBJN-FWWHASMVSA-N
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Compound Information
Molecular Weight:156.2652
Molecular Formula:C10H20O
InChIKey:CCOQPGVQAWPUPE-KYZUINATSA-N
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Compound Information
Molecular Weight:100.1158
Molecular Formula:C5H8O2
InChIKey:VVQNEPGJFQJSBK-UHFFFAOYSA-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:173.299
Molecular Formula:C9H23N3
InChIKey:UKODFQOELJFMII-UHFFFAOYSA-N
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Compound Information
Molecular Weight:195.054
Molecular Formula:C6H11BrO2
InChIKey:XIMFCGSNSKXPBO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:182.261
Molecular Formula:C14H14
InChIKey:QWUWMCYKGHVNAV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:93.1265
Molecular Formula:C6H7N
InChIKey:PAYRUJLWNCNPSJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:214.732
Molecular Formula:C12H19ClO
InChIKey:JXHVOGFWCCXITB-NWDGAFQWSA-N
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Compound Information
Molecular Weight:281.563
Molecular Formula:C11H11Cl3O2
InChIKey:ILXMVDZJBQRNIZ-PKGCAQHRSA-N
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Compound Information
Molecular Weight:204.2649
Molecular Formula:C13H16O2
InChIKey:VGWMVFUSNDYZPC-MDZDMXLPSA-N
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Compound Information
Molecular Weight:122.1644
Molecular Formula:C8H10O
InChIKey:WAPNOHKVXSQRPX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:294.3908
Molecular Formula:C19H22N2O
InChIKey:Not Available
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Compound Information
Molecular Weight:150.36
Molecular Formula:Sm
InChIKey:KZUNJOHGWZRPMI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:265.3496
Molecular Formula:C18H19NO
InChIKey:PDSGNCLCMINFGM-XNWCZRBMSA-N
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Compound Information
Molecular Weight:149.89424
Molecular Formula:INa
InChIKey:FVAUCKIRQBBSSJ-UHFFFAOYSA-M
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Compound Information
Molecular Weight:168.2328
Molecular Formula:C10H16O2
InChIKey:ARNPQYFYGKMXGD-RKDXNWHRSA-N
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Compound Information
Molecular Weight:122.1246
Molecular Formula:C6H6N2O
InChIKey:VFQXVTODMYMSMJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:166.26
Molecular Formula:C11H18O
InChIKey:CAEPRMOSWPLBAF-CMDGGOBGSA-N
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Compound Information
Molecular Weight:86.0892
Molecular Formula:C4H6O2
InChIKey:CERQOIWHTDAKMF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:198.2604
Molecular Formula:C14H14O
InChIKey:GBGXVCNOKWAMIP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:198.3019
Molecular Formula:C12H22O2
InChIKey:WDQMWEYDKDCEHT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:152.2334
Molecular Formula:C10H16O
InChIKey:Not Available
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Compound Information
Molecular Weight:128.1705
Molecular Formula:C10H8
InChIKey:UFWIBTONFRDIAS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:319.3523
Molecular Formula:C17H21NO5
InChIKey:ZAPZVXGIEUSDKK-DSLXRWPSSA-N
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Compound Information
Molecular Weight:128.169
Molecular Formula:C7H12O2
InChIKey:Not Available
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Compound Information
Molecular Weight:212.309
Molecular Formula:C11H16O2S
InChIKey:QQUIRZQVCSQUCX-DTWKUNHWSA-N
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Compound Information
Molecular Weight:272.2512
Molecular Formula:C12H16O7
InChIKey:Not Available
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Compound Information
Molecular Weight:73.1119
Molecular Formula:C4H8O
InChIKey:Not Available
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Compound Information
Molecular Weight:312.5197
Molecular Formula:C17H32O3Si
InChIKey:XLRLCHHCYHEYBE-BYNSBNAKSA-N
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Compound Information
Molecular Weight:190.038
Molecular Formula:C6H8BrNO
InChIKey:OQWAOAIUESMDOS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:305.154
Molecular Formula:C13H14Cl2O4
InChIKey:KZYWJCVGHFXOEL-SSTWFLKASA-N
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Compound Information
Molecular Weight:152.1506
Molecular Formula:C7H8N2O2
InChIKey:Not Available
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Compound Information
Molecular Weight:140.567
Molecular Formula:C7H5ClO
InChIKey:FPYUJUBAXZAQNL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:98.143
Molecular Formula:C6H10O
InChIKey:Not Available
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Compound Information
Molecular Weight:344.426
Molecular Formula:C22H16O2S
InChIKey:DGGONIYYSSURKZ-GRGXKFILSA-N
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Compound Information
Molecular Weight:183.249
Molecular Formula:C13H13N
InChIKey:Not Available
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Compound Information
Molecular Weight:108.0948
Molecular Formula:C6H4O2
InChIKey:AZQWKYJCGOJGHM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:212.2854
Molecular Formula:C12H20O3
InChIKey:PYYTZYJVDLGOIF-UKKRHICBSA-N
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Compound Information
Molecular Weight:247.118
Molecular Formula:C11H12Cl2O2
InChIKey:GZJFCEONMGFSJL-PPGDXSCSSA-N
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Compound Information
Molecular Weight:112.1265
Molecular Formula:C6H8O2
InChIKey:MMLJDECBZWQXCV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:154.594
Molecular Formula:C8H7ClO
InChIKey:Not Available
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Compound Information
Molecular Weight:218.2469
Molecular Formula:C10H18O5
InChIKey:XYVHRFVONMVDGK-MRVPVSSYSA-N
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Compound Information
Molecular Weight:153.1354
Molecular Formula:C7H7NO3
InChIKey:HBROZNQEVUILML-UHFFFAOYSA-N
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Compound Information
Molecular Weight:155.582
Molecular Formula:C7H6ClNO
InChIKey:MJTGQALMWUUPQM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:206.2824
Molecular Formula:C16H14
InChIKey:VPPCQVCZKDIGGG-IYBDPMFKSA-N
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Compound Information
Molecular Weight:130.0987
Molecular Formula:C5H6O4
InChIKey:LVHBHZANLOWSRM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:446.6948
Molecular Formula:C26H42O4Si
InChIKey:AECLRBFRXQRPCD-KATYJPCHSA-N
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Compound Information
Molecular Weight:196.286
Molecular Formula:C12H20O2
InChIKey:MXDOVFKXSLSLDC-ONNFQVAWSA-N
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Compound Information
Molecular Weight:138.2069
Molecular Formula:C9H14O
InChIKey:AQDZXPLGDCMLEH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:187.034
Molecular Formula:C7H7BrO
InChIKey:QJPJQTDYNZXKQF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:17.0305
Molecular Formula:H3N
InChIKey:QGZKDVFQNNGYKY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:137.136
Molecular Formula:C7H7NO2
InChIKey:VDEUYMSGMPQMIK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:120.1485
Molecular Formula:C8H8O
InChIKey:DTUQWGWMVIHBKE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:165.028
Molecular Formula:C5H9BrO
InChIKey:VOHILFSOWRNVJJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:314.5356
Molecular Formula:C17H34O3Si
InChIKey:YONYVIFXZQRFEG-HUUCEWRRSA-N
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Compound Information
Molecular Weight:130.572
Molecular Formula:C6H7ClO
InChIKey:RGFCOYSMOSCVGR-WDSKDSINSA-N
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Compound Information
Molecular Weight:121.1366
Molecular Formula:C7H7NO
InChIKey:KXDAEFPNCMNJSK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:182.647
Molecular Formula:C10H11ClO
InChIKey:ROBIRMGNXQRWLM-ZJUUUORDSA-N
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Compound Information
Molecular Weight:281.392
Molecular Formula:C19H23NO
InChIKey:BIFDIFHNLBZMRG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:41.0519
Molecular Formula:C2H3N
InChIKey:WEVYAHXRMPXWCK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:116.1583
Molecular Formula:C6H12O2
InChIKey:OVBFMEVBMNZIBR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:128.212
Molecular Formula:C8H16O
InChIKey:NUJGJRNETVAIRJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:210.228
Molecular Formula:C14H10O2
InChIKey:WURBFLDFSFBTLW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:300.4351
Molecular Formula:C20H28O2
InChIKey:AZQAIRJYCUWZPD-SLHNCBLASA-N
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Compound Information
Molecular Weight:147.1739
Molecular Formula:C9H9NO
InChIKey:APEJMQOBVMLION-VOTSOKGWSA-N
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Compound Information
Molecular Weight:107.1531
Molecular Formula:C7H9N
InChIKey:WGQKYBSKWIADBV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:236.3514
Molecular Formula:C18H20
InChIKey:YGTRBFXKKOTLKK-OWOJBTEDSA-N
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Compound Information
Molecular Weight:158.2396
Molecular Formula:C12H14
InChIKey:ZVNDSQGHZLPKQV-UXBLZVDNSA-N
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Compound Information
Molecular Weight:100.1589
Molecular Formula:C6H12O
InChIKey:PFCHFHIRKBAQGU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:148.2017
Molecular Formula:C10H12O
InChIKey:IAHCIRBKFCOPEE-XBXARRHUSA-N
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