Standard Article

Epoxide Migration (Payne Rearrangement) and Related Reactions

  1. Robert M. Hanson

Published Online: 15 APR 2004

DOI: 10.1002/0471264180.or060.01

Organic Reactions

Organic Reactions

How to Cite

Hanson, R. M. 2004. Epoxide Migration (Payne Rearrangement) and Related Reactions. Organic Reactions. 60:1:1–156.

Author Information

  1. St. Olaf College, Department of Chemistry, Northfield, Minnesota

Publication History

  1. Published Online: 15 APR 2004

Chemistry Terms

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Abstract

Under a variety of basic conditions, 2,3-epoxy alcohols rearrange with inversion at C-2. The reaction, originally referred to in the literature as the β-oxanol rearrangement, is now exclusively referred to as epoxide migration or Payne rearrangement.

Epoxide migration is reversible, often leading to a mixture of epoxy alcohol isomers. Furthermore, in the presence of hydroxide or other nucleophiles, in situ opening of the equilibrating species may be observed. When such opening is desired, epoxide migration becomes a powerful method for the introduction of functionality into a substrate containing a 2,3-epoxy alcohol moiety. However, when opening is not desired, epoxide migration can become a significant problem.

The epoxide migration process lends itself to other synthetically useful manipulations. For example, the anionic equilibrating species may also be trapped with electrophiles such as alkyl and silyl halides, alkyl sulfonates, and epoxides. Electrophilic trapping may be inter- or intramolecular, and has been used as a means of delivering functionality to either C-2 or C-3 selectively.

The intent of this chapter is to provide a comprehensive review of epoxide migration, including factors influencing the equilibrium position, conditions leading to in situ epoxide opening, and examples of electrophilic trapping. The reaction is discussed in relation to its utility as a synthetic method as well as its prevention as an unwanted side reaction.

Related rearrangements in which either the epoxide or hydroxy oxygen has been replaced with nitrogen or sulfur have also been studied. These reactions, referred to in the literature as aza-Payne and thia-Payne rearrangements, respectively, are comprehensively included in this chapter as well. For the purposes of this discussion, the term “forward” aza-Payne rearrangement refers to the direction of reaction leading from oxirane to aziridine. Similarly, “forward” thia-Payne rearrangement refers to the direction of reaction leading from oxirane to thiirane. In the case of aza-Payne rearrangements, both forward and reverse reactions have been effected, and in this chapter the term “reverse” aza-Payne rearrangement refers to reactions leading from aziridine to oxirane.

Epoxides have long been considered important in the chemistry of carbohydrates, and epoxide migration in the context of carbohydrate chemistry has been discussed in several reviews. In addition, particularly since discovery of the catalytic asymmetric epoxidation of allylic alcohols and the rise in importance of enantiomerically enriched acyclic epoxy alcohols, epoxide migration with in situ opening in acyclic systems has been much studied. The tabular survey summarizes the literature of epoxide migration and related reactions, including equilibration, in situ opening and trapping, aza-Payne rearrangements, and thia-Payne rearrangements, from 1931 to 1999. Reports referring to reactions involving addition at C-1 or C-3 without inversion of stereochemistry at C-2 as “Payne rearrangements” are not covered in this review.

Keywords:

  • mechanism;
  • stereochemistry;
  • epoxide migration;
  • thermodynamics;
  • kinetic control;
  • epoxide migration;
  • payne rearrangement;
  • nonbasic conditions;
  • nucleophilic trapping;
  • electrophilic trapping;
  • aza-payne rearrangements;
  • thia-payne rearrangements;
  • scope;
  • limitations;
  • equilibration;
  • acyclic systems;
  • nucleophilic opening;
  • three-step equivalent sequence;
  • diol-sulfide method;
  • opening method;
  • synthesis;
  • chirality inversion;
  • cyclic systems;
  • comparison of methods;
  • asymmetric dihydroxylation;
  • stereochemical reaction sequence;
  • neighboring group assistance;
  • cyclic sulfate;
  • c-3 sulfonate;
  • diol-sulfonate;
  • titanium mediated;
  • lithium salt induced

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Compound Information
Molecular Weight:0
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:186.2481
Molecular Formula:C10H18O3
InChIKey:QZRANJWXTXXQQC-JDOFKEMOSA-N
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Molecular Weight:142.1956
Molecular Formula:C8H14O2
InChIKey:RBBFNGJOCUWHJK-SSDOTTSWSA-N
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Molecular Weight:167.247
Molecular Formula:C9H11OS
InChIKey:XAUCNYJDSRVYIB-FTNKSUMCSA-N
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Compound Information
Molecular Weight:496.618
Molecular Formula:C27H32N2O5S
InChIKey:IFMCALYTEZKHOU-LSWLQPCBSA-N
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Compound Information
Molecular Weight:303.3726
Molecular Formula:C21H18O2
InChIKey:Not Available
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Molecular Weight:243.323
Molecular Formula:C11H17NO3S
InChIKey:GRSGFXPLGMIDCW-SNVBAGLBSA-N
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Compound Information
Molecular Weight:303.149
Molecular Formula:C12H15BrO4
InChIKey:YSDLGIIFWAUNHX-RHYQMDGZSA-N
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Molecular Weight:282.3768
Molecular Formula:C19H22O2
InChIKey:YQVPKRMPLFOWRL-OTWHNJEPSA-N
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Molecular Weight:Not Available
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Molecular Weight:110.177
Molecular Formula:C6H6S
InChIKey:RMVRSNDYEFQCLF-UHFFFAOYSA-N
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Molecular Weight:174.1944
Molecular Formula:C8H14O4
InChIKey:DNOZLDKRFCLWTL-RNFRBKRXSA-N
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Molecular Weight:Not Available
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Molecular Weight:84.1164
Molecular Formula:C5H8O
InChIKey:ICMWSAALRSINTC-UHFFFAOYSA-N
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Molecular Weight:42.394
Molecular Formula:ClLi
InChIKey:KWGKDLIKAYFUFQ-UHFFFAOYSA-M
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Molecular Weight:Not Available
Molecular Formula:Not Available
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Molecular Weight:210.336
Molecular Formula:C12H18OS
InChIKey:XRRRMYUUPRXRLA-UHFFFAOYSA-N
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Molecular Weight:304.402
Molecular Formula:C14H24O5S
InChIKey:PFMVRKIIVWMVLW-RWMBFGLXSA-N
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Molecular Weight:380.5
Molecular Formula:C23H24O3S
InChIKey:ZOKSTJRDLIYLLO-FCHUYYIVSA-N
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Molecular Weight:104.214
Molecular Formula:C5H12S
InChIKey:CJFVCTVYZFTORU-UHFFFAOYSA-N
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Molecular Weight:157.3287
Molecular Formula:C8H19NSi
InChIKey:WLADIVUISABQHN-UHFFFAOYSA-N
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Molecular Weight:222.2372
Molecular Formula:C12H14O4
InChIKey:GOKFKMWTGYINLH-BJDJZHNGSA-N
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Molecular Weight:194.2271
Molecular Formula:C11H14O3
InChIKey:KSQBAPLQXNCSOC-MNOVXSKESA-N
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Molecular Weight:184.716
Molecular Formula:C8H18CuLi
InChIKey:UADBHFTWQBWLOF-UHFFFAOYSA-N
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Molecular Weight:284.414
Molecular Formula:C15H24O3S
InChIKey:VOFWZENRXAIZHS-KBPBESRZSA-N
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Molecular Weight:648.7854
Molecular Formula:C44H40O5
InChIKey:UETSAUNORDHDBX-GLGKVNTQSA-N
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Molecular Weight:17.0305
Molecular Formula:H3N
InChIKey:QGZKDVFQNNGYKY-UHFFFAOYSA-N
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Molecular Weight:662.7875
Molecular Formula:C38H55CoN2O4
InChIKey:SZLTZRSRNDSBPH-OHRASPNLSA-K
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Compound Information
Molecular Weight:350.4923
Molecular Formula:C21H34O4
InChIKey:PCSYHGQVLFQXBT-RLETZYLZSA-N
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Molecular Weight:Not Available
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Molecular Weight:180.267
Molecular Formula:C10H12OS
InChIKey:HFANZUMLJHKXNO-WPRPVWTQSA-N
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Molecular Weight:146.1412
Molecular Formula:C6H10O4
InChIKey:YCRYRWDWBHKSKR-OMMKOOBNSA-N
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Molecular Weight:304.404
Molecular Formula:C17H20O3S
InChIKey:OCVOQEIDWMANBG-IRXDYDNUSA-N
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Molecular Weight:196.309
Molecular Formula:C11H16OS
InChIKey:GJCOVXIWNBZFDP-UWVGGRQHSA-N
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Compound Information
Molecular Weight:102.1317
Molecular Formula:C5H10O2
InChIKey:GDUKJERMEWMMMD-SCSAIBSYSA-N
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Compound Information
Molecular Weight:133.845
Molecular Formula:ILi
InChIKey:HSZCZNFXUDYRKD-UHFFFAOYSA-M
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Compound Information
Molecular Weight:87.1204
Molecular Formula:C4H9NO
InChIKey:DQFJZBVPOLGQMB-IMJSIDKUSA-N
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Compound Information
Molecular Weight:182.358
Molecular Formula:C9H14SSi
InChIKey:VJMQFIRIMMSSRW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:228.2848
Molecular Formula:C12H20O4
InChIKey:AHPZYAGHNPQCBR-OJBNZGHXSA-N
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Molecular Weight:Not Available
Molecular Formula:Not Available
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Compound Information
Molecular Weight:57.0422
Molecular Formula:CH3NaO
InChIKey:Not Available
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Molecular Weight:68.0773
Molecular Formula:C3H4N2
InChIKey:RAXXELZNTBOGNW-UHFFFAOYSA-N
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Molecular Weight:245.4014
Molecular Formula:C14H31NO2
InChIKey:WGEUSVPHSCZWHC-UONOGXRCSA-N
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Compound Information
Molecular Weight:37.833
Molecular Formula:BH4Na
InChIKey:YOQDYZUWIQVZSF-UHFFFAOYSA-N
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Molecular Weight:354.481
Molecular Formula:C20H34O5
InChIKey:GOHNIXDAQODZKP-PBFVXXSYSA-N
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Molecular Weight:73.0938
Molecular Formula:C3H7NO
InChIKey:ZMXDDKWLCZADIW-UHFFFAOYSA-N
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Molecular Weight:251.09
Molecular Formula:C3N3Yb
InChIKey:SRXVQPQVWWWBEG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:175.1598
Molecular Formula:C7H12O5
InChIKey:PFESSILSNGJLKQ-ZDLURKLDSA-M
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Molecular Weight:150.1745
Molecular Formula:C9H10O2
InChIKey:PVALSANGMFRTQM-IUCAKERBSA-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:284.215
Molecular Formula:C12H28O4Ti
InChIKey:VXUYXOFXAQZZMF-UHFFFAOYSA-N
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Molecular Weight:56.1056
Molecular Formula:HKO
InChIKey:KWYUFKZDYYNOTN-UHFFFAOYSA-M
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Molecular Weight:227.28
Molecular Formula:C10H13NO3S
InChIKey:JYNOTASVIQWSJV-VIFPVBQESA-N
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Compound Information
Molecular Weight:648.7854
Molecular Formula:C44H40O5
InChIKey:HZMVCAYHWFUGQC-MVJOSCLSSA-N
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Compound Information
Molecular Weight:154.261
Molecular Formula:C7H15AlSi
InChIKey:WHBBQPNENXSLAJ-UHFFFAOYSA-N
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Molecular Weight:Not Available
Molecular Formula:Not Available
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Molecular Weight:Not Available
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Molecular Weight:360.608
Molecular Formula:C20H30NOSSi
InChIKey:NLIWXUGKXKNUFZ-VQTJNVASSA-N
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Molecular Weight:Not Available
Molecular Formula:Not Available
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Molecular Weight:262.452
Molecular Formula:C14H30O2S
InChIKey:YLDVKPXFHMKSRG-CHWSQXEVSA-N
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Molecular Weight:244.0707
Molecular Formula:C6H13IO2
InChIKey:VRYSWSRMFYBDJL-WDSKDSINSA-N
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Molecular Weight:194.2271
Molecular Formula:C11H14O3
InChIKey:ISCSDUBWWFMCCR-QWRGUYRKSA-N
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Molecular Weight:142.1956
Molecular Formula:C8H14O2
InChIKey:HXZKAJGYSHZZAS-ZETCQYMHSA-N
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Molecular Weight:182.2594
Molecular Formula:C11H18O2
InChIKey:CLQUALZGWGWQRC-JTQLQIEISA-N
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Molecular Weight:300.415
Molecular Formula:C18H20O2S
InChIKey:SIYFFJQMNGWJNT-ROUUACIJSA-N
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Compound Information
Molecular Weight:132.181
Molecular Formula:C5H8O2S
InChIKey:OOQMOSTZRNAKLX-RXMQYKEDSA-N
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Molecular Weight:179.2157
Molecular Formula:C10H13NO2
InChIKey:DSIGENAIQZTQHN-GUBZILKMSA-N
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Molecular Weight:Not Available
Molecular Formula:Not Available
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Molecular Weight:398.11
Molecular Formula:C6H18CuLiSn2
InChIKey:ALRIDXXWAMMQNW-UHFFFAOYSA-N
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Molecular Weight:173.2096
Molecular Formula:C8H15NO3
InChIKey:CFIQLGGGUSYWKT-VJSCVCEBSA-N
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Molecular Weight:129.2001
Molecular Formula:C7H15NO
InChIKey:RRNALROYPBFHNH-RQJHMYQMSA-N
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Molecular Weight:141.928
Molecular Formula:C4H10BF3O
InChIKey:MZTVMRUDEFSYGQ-UHFFFAOYSA-N
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Molecular Weight:285.402
Molecular Formula:C14H23NO3S
InChIKey:XHYYVAFYXYUWJE-CYBMUJFWSA-N
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Molecular Weight:151.184
Molecular Formula:C4H9NO3S
InChIKey:YDJIQPVVDFTLQG-BYPYZUCNSA-N
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Compound Information
Molecular Weight:194.293
Molecular Formula:C11H14OS
InChIKey:JBMSZJIVZGSSEB-JTQLQIEISA-N
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Compound Information
Molecular Weight:216.865
Molecular Formula:C6H18CuLiSi2
InChIKey:AUDJHDOZSPHVJB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Molecular Weight:282.3768
Molecular Formula:C19H22O2
InChIKey:YTSRDNVMYKDWGP-FHWLQOOXSA-N
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Molecular Weight:222.258
Molecular Formula:C4H9F3O3SSi
InChIKey:FTVLMFQEYACZNP-UHFFFAOYSA-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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Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:116.1583
Molecular Formula:C6H12O2
InChIKey:IGRZECZSICIWJA-WDSKDSINSA-N
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Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Molecular Weight:241.307
Molecular Formula:C11H15NO3S
InChIKey:CNNDHFPJCKVZSL-ONGXEEELSA-N
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Compound Information
Molecular Weight:307.965
Molecular Formula:C6H12Br2O4
InChIKey:GPDZJUZKDUGOFI-SLPGGIOYSA-N
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Compound Information
Molecular Weight:133.404
Molecular Formula:C2H3Cl3
InChIKey:Not Available
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Compound Information
Molecular Weight:208.32
Molecular Formula:C12H16OS
InChIKey:KQUNBWKILNKIKZ-RYUDHWBXSA-N
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Compound Information
Molecular Weight:179.2157
Molecular Formula:C10H13NO2
InChIKey:IUYSHMVMQPAUHB-LPEHRKFASA-N
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Compound Information
Molecular Weight:295.397
Molecular Formula:C15H21NO3S
InChIKey:VBBVKZMHWXOTIE-LBAUFKAWSA-N
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Compound Information
Molecular Weight:100.1158
Molecular Formula:C5H8O2
InChIKey:JOODUMVMXMJPTD-WHFBIAKZSA-N
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Compound Information
Molecular Weight:194.292
Molecular Formula:C8H18O3S
InChIKey:ZUHJKOJHCBWISJ-RNFRBKRXSA-N
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Compound Information
Molecular Weight:88.1051
Molecular Formula:C4H8O2
InChIKey:LEJLUUHSOFWJSW-QWWZWVQMSA-N
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Compound Information
Molecular Weight:208.2967
Molecular Formula:C13H20O2
InChIKey:NWIYCNLONAJSAP-WOPDTQHZSA-N
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Compound Information
Molecular Weight:80.055
Molecular Formula:C4H9LiO
InChIKey:LZWQNOHZMQIFBX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:257.349
Molecular Formula:C12H19NO3S
InChIKey:OHPJJGSDCWYOBX-JQWIXIFHSA-N
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Compound Information
Molecular Weight:166.2394
Molecular Formula:C10H19Al
InChIKey:XAQDFDBRRMIVBZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:102.0886
Molecular Formula:C4H6O3
InChIKey:Not Available
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Molecular Weight:179.2004
Molecular Formula:C6H18N3OP
InChIKey:GNOIPBMMFNIUFM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:167.2804
Molecular Formula:C8H13NOSi
InChIKey:FZKWXWQVJUGUBH-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:295.4186
Molecular Formula:C20H25NO
InChIKey:SRWDUGYKKYZALS-PMACEKPBSA-N
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Compound Information
Molecular Weight:260.192
Molecular Formula:C12H14ArNO3
InChIKey:CKVHXBGIPOHBLG-MKURHVDASA-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:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:281.508
Molecular Formula:C15H25OSSi
InChIKey:JTIIWUNPANRWHI-BTPDTDQASA-N
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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:102.1317
Molecular Formula:C5H10O2
InChIKey:HJCWXVWXDOBZTQ-CRCLSJGQSA-N
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Compound Information
Molecular Weight:90.121
Molecular Formula:C4H10O2
InChIKey:CIHOLLKRGTVIJN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:151.184
Molecular Formula:C4H9NO3S
InChIKey:KGPZVZBZYXTRAW-CNZKWPKMSA-N
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Compound Information
Molecular Weight:73.0938
Molecular Formula:C3H7NO
InChIKey:AFEQENGXSMURHA-VKHMYHEASA-N
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Compound Information
Molecular Weight:166.24
Molecular Formula:C9H10OS
InChIKey:MYBWNWNBXBBZKW-MRVPVSSYSA-N
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Compound Information
Molecular Weight:72.0851
Molecular Formula:C3H9Al
InChIKey:Not Available
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Compound Information
Molecular Weight:180.2005
Molecular Formula:C10H12O3
InChIKey:ICUOMJATRWGNFI-NXEZZACHSA-N
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Compound Information
Molecular Weight:144.1253
Molecular Formula:C6H8O4
InChIKey:RXDFVNWKKAAOSK-AIECOIEWSA-N
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Compound Information
Molecular Weight:121.93
Molecular Formula:C6H7BO2
InChIKey:HXITXNWTGFUOAU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:87.1204
Molecular Formula:C4H9NO
InChIKey:KHNYMEREXRKTPV-IUYQGCFVSA-N
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Compound Information
Molecular Weight:176.1672
Molecular Formula:C7H12O5
InChIKey:UUCZNBCOKXSKLU-VPLCAKHXSA-N
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Compound Information
Molecular Weight:223.3113
Molecular Formula:C13H21NO2
InChIKey:FECLWKFQDSRNIN-OLZOCXBDSA-N
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Compound Information
Molecular Weight:295.397
Molecular Formula:C15H21NO3S
InChIKey:ZWNQPGJCMHSOKX-CQSZACIVSA-N
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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:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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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:331.225
Molecular Formula:C13H15BrO3S
InChIKey:URRFOMUERIZHNX-OLZOCXBDSA-N
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Compound Information
Molecular Weight:73.1368
Molecular Formula:C4H11N
InChIKey:HPNMFZURTQLUMO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:91.1091
Molecular Formula:C3H9NO2
InChIKey:KQIGMPWTAHJUMN-VKHMYHEASA-N
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Compound Information
Molecular Weight:490.2862
Molecular Formula:C19H23IO7
InChIKey:AARXRFRYSYLKNB-QNWHSYCASA-N
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Compound Information
Molecular Weight:102.1317
Molecular Formula:C5H10O2
InChIKey:XEVKRTIYWSUXHP-WHFBIAKZSA-N
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Compound Information
Molecular Weight:254.305
Molecular Formula:C11H14N2O3S
InChIKey:NGTQLAWCXWOPDQ-SNVBAGLBSA-N
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Compound Information
Molecular Weight:23.948
Molecular Formula:HLiO
InChIKey:WMFOQBRAJBCJND-UHFFFAOYSA-M
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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:316.327
Molecular Formula:C13H16O7S
InChIKey:FHTOBDYSLIUDCH-UJPOAAIJSA-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:131.2483
Molecular Formula:C5H13NOSi
InChIKey:RAZBQBDVZOHZPS-AATRIKPKSA-N
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Compound Information
Molecular Weight:112.034
Molecular Formula:C3H6ArNO
InChIKey:SENRVNPKOFAENK-VKHMYHEASA-N
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Compound Information
Molecular Weight:392.1
Molecular Formula:C13H23NO3SSn
InChIKey:HCXWUABHZAECTE-RASHCQHBSA-N
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Compound Information
Molecular Weight:130.1849
Molecular Formula:C7H14O2
InChIKey:AHEQFVNIXIPVFB-WDSKDSINSA-N
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Compound Information
Molecular Weight:111.539
Molecular Formula:C2H3CuLiN
InChIKey:DLLMDMUKOUIKRZ-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:180.2005
Molecular Formula:C10H12O3
InChIKey:XWTBATKEBUFLQD-UWVGGRQHSA-N
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Compound Information
Molecular Weight:100.556
Molecular Formula:C2H6CuLi
InChIKey:LQCYIQBYFCQMCH-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:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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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:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:289.189
Molecular Formula:C11H13BrO2S
InChIKey:YHIHVMPBSKSZJT-GHMZBOCLSA-N
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Compound Information
Molecular Weight:112.034
Molecular Formula:C3H6ArNO
InChIKey:VEVBICWAIBUJOA-VXPOTGITSA-N
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Compound Information
Molecular Weight:114.1648
Molecular Formula:C6H15Al
InChIKey:VOITXYVAKOUIBA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:86.845
Molecular Formula:BrLi
InChIKey:AMXOYNBUYSYVKV-UHFFFAOYSA-M
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Compound Information
Molecular Weight:303.3726
Molecular Formula:C21H18O2
InChIKey:Not Available
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Compound Information
Molecular Weight:104.1045
Molecular Formula:C4H8O3
InChIKey:KRBIHOANUQUSRV-IMJSIDKUSA-N
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Compound Information
Molecular Weight:116.1583
Molecular Formula:C6H12O2
InChIKey:REBJJHOONXCNHP-CRCLSJGQSA-N
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Compound Information
Molecular Weight:260.192
Molecular Formula:C12H14ArNO3
InChIKey:XRLJURCSYCKXRK-RHYQMDGZSA-N
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Compound Information
Molecular Weight:78.581
Molecular Formula:CH3Cu
InChIKey:HRNSPWKFRJGQEC-UHFFFAOYSA-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:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:301.477
Molecular Formula:C13H23NO3SSi
InChIKey:PKESGWJFLQNRPN-LBPRGKRZSA-N
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Compound Information
Molecular Weight:241.307
Molecular Formula:C11H15NO3S
InChIKey:DSUQRBHLWFVFKB-WKAHHKJFSA-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:88.1051
Molecular Formula:C4H8O2
InChIKey:RYHBNJHYFVUHQT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:496.618
Molecular Formula:C27H32N2O5S
InChIKey:UBCNOFBSBXMUMO-BLNIWHHLSA-N
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Compound Information
Molecular Weight:318.4504
Molecular Formula:C20H30O3
InChIKey:MFIWRSIQAIKKEY-BYWOILJTSA-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:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:112.212
Molecular Formula:C4H9KO
InChIKey:CUQOHAYJWVTKDE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:264.3154
Molecular Formula:C12H24O6
InChIKey:XEZNGIUYQVAUSS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:222.2372
Molecular Formula:C12H14O4
InChIKey:HNEAZOAYLSDFTC-BJDJZHNGSA-N
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Compound Information
Molecular Weight:534.705
Molecular Formula:C29H42O7S
InChIKey:MLBFVBXEEPZPRV-WQXHAXCJSA-N
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Compound Information
Molecular Weight:115.2092
Molecular Formula:C3H9N3Si
InChIKey:SEDZOYHHAIAQIW-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:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:146.1412
Molecular Formula:C6H10O4
InChIKey:KLDXJTOLSGUMSJ-FSIIMWSLSA-N
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Compound Information
Molecular Weight:144.1253
Molecular Formula:C6H8O4
InChIKey:NDCSJPPJAVCLMI-VFUOTHLCSA-N
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Compound Information
Molecular Weight:153.619
Molecular Formula:C5H9CuLiN
InChIKey:OSNVBBZZYODGIT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:120.976
Molecular Formula:C3H5Br
InChIKey:BHELZAPQIKSEDF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:130.1849
Molecular Formula:C7H14O2
InChIKey:QEKXTZAXJWVFRN-RITPCOANSA-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:404.33
Molecular Formula:C24H25BO3S
InChIKey:RPIVAGAKKUIMFG-ZEQRLZLVSA-N
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Compound Information
Molecular Weight:175.1598
Molecular Formula:C7H12O5
InChIKey:VXXOBEONOIPHKJ-BFHQHQDPSA-M
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Compound Information
Molecular Weight:129.2001
Molecular Formula:C7H15NO
InChIKey:FUPILNHIQXNRTL-BQBZGAKWSA-N
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Compound Information
Molecular Weight:146.1412
Molecular Formula:C6H10O4
InChIKey:YLCXEYPUYRBLSN-SLPGGIOYSA-N
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Compound Information
Molecular Weight:210.336
Molecular Formula:C12H18OS
InChIKey:UVIJANZULUFXNA-NSHDSACASA-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:270.323
Molecular Formula:C17H18O3
InChIKey:SJLRAEMAPCCLJW-HOTGVXAUSA-N
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Compound Information
Molecular Weight:105.943
Molecular Formula:C6H16BLi
InChIKey:WCJAYABJWDIZAJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:140.2584
Molecular Formula:C6H12N2Si
InChIKey:YKFRUJSEPGHZFJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:90.144
Molecular Formula:C3H6OS
InChIKey:RFTGJEJQDSTVSI-VKHMYHEASA-N
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Compound Information
Molecular Weight:41.9881725
Molecular Formula:FNa
InChIKey:PUZPDOWCWNUUKD-UHFFFAOYSA-M
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Compound Information
Molecular Weight:90.187
Molecular Formula:C4H10S
InChIKey:WMXCDAVJEZZYLT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:162.1406
Molecular Formula:C6H10O5
InChIKey:TWNIBLMWSKIRAT-VFUOTHLCSA-N
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Compound Information
Molecular Weight:88.1051
Molecular Formula:C4H8O2
InChIKey:QQHZNUPEBVRUFO-DMTCNVIQSA-N
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Compound Information
Molecular Weight:104.1045
Molecular Formula:C4H8O3
InChIKey:PENWRXZLRDTNBI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:239.064
Molecular Formula:C7H11BrO4
InChIKey:QOBBTLKYZTXLDU-WYDQCIBASA-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:227.004
Molecular Formula:C8Cl2N2O2
InChIKey:HZNVUJQVZSTENZ-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:173.2096
Molecular Formula:C8H15NO3
InChIKey:ZBBGKXNNTNBRBH-LURJTMIESA-N
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Compound Information
Molecular Weight:99.2065
Molecular Formula:C4H9NSi
InChIKey:Not Available
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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:172.2646
Molecular Formula:C10H20O2
InChIKey:MZPZDPXPQAQGJD-ZJUUUORDSA-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:174.1944
Molecular Formula:C8H14O4
InChIKey:ZWGPMXJKSSFLBU-RNFRBKRXSA-N
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Compound Information
Molecular Weight:362.3738
Molecular Formula:C19H22O7
InChIKey:GHWOQFZWXKNOMS-RRMRAJRUSA-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:74.0785
Molecular Formula:C3H6O2
InChIKey:CTKINSOISVBQLD-VKHMYHEASA-N
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Compound Information
Molecular Weight:73.0938
Molecular Formula:C3H7NO
InChIKey:KRUMYKPXYLURIT-GSVOUGTGSA-N
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Compound Information
Molecular Weight:227.28
Molecular Formula:C10H13NO3S
InChIKey:BDBQXGZJGMVTGC-BFHBGLAWSA-N
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Compound Information
Molecular Weight:100.1158
Molecular Formula:C5H8O2
InChIKey:YYUNQECXARGEAQ-CRCLSJGQSA-N
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Compound Information
Molecular Weight:36.0665
Molecular Formula:CH4O
InChIKey:Not Available
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Compound Information
Molecular Weight:116.1583
Molecular Formula:C6H12O2
InChIKey:YSDUPQNXIOJZPX-WHFBIAKZSA-N
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Compound Information
Molecular Weight:117.1644
Molecular Formula:C6H12O2
InChIKey:Not Available
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Compound Information
Molecular Weight:117.1644
Molecular Formula:C6H12O2
InChIKey:Not Available
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Compound Information
Molecular Weight:41.0033
Molecular Formula:HNaO
InChIKey:Not Available
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Compound Information
Molecular Weight:20.0276
Molecular Formula:H2O
InChIKey:Not Available
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Compound Information
Molecular Weight:144.1253
Molecular Formula:C6H8O4
InChIKey:NDCSJPPJAVCLMI-FDROIEKHSA-N
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Compound Information
Molecular Weight:104.1045
Molecular Formula:C4H8O3
InChIKey:PENWRXZLRDTNBI-ZXZARUISSA-N
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Compound Information
Molecular Weight:172.2646
Molecular Formula:C10H20O2
InChIKey:MZPZDPXPQAQGJD-UWVGGRQHSA-N
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Compound Information
Molecular Weight:162.1406
Molecular Formula:C6H10O5
InChIKey:TWNIBLMWSKIRAT-FPRJBGLDSA-N
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Compound Information
Molecular Weight:307.965
Molecular Formula:C6H12Br2O4
InChIKey:GPDZJUZKDUGOFI-KVTDHHQDSA-N
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Compound Information
Molecular Weight:194.2271
Molecular Formula:C11H14O3
InChIKey:KSQBAPLQXNCSOC-WDEREUQCSA-N
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Compound Information
Molecular Weight:210.2695
Molecular Formula:C12H18O3
InChIKey:BYMYOHZJXFUGEY-VXGBXAGGSA-N
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Compound Information
Molecular Weight:390.5179
Molecular Formula:C25H30N2O2
InChIKey:WMVGOTZLWPJDFO-RPWUZVMVSA-N
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Compound Information
Molecular Weight:293.467
Molecular Formula:C17H27NOS
InChIKey:PXUBVQYTPQFMLX-DLBZAZTESA-N
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Compound Information
Molecular Weight:120.384
Molecular Formula:CHCl3
InChIKey:Not Available
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Compound Information
Molecular Weight:102.1317
Molecular Formula:C5H10O2
InChIKey:VGNAVRBYWQFGOQ-WHFBIAKZSA-N
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Compound Information
Molecular Weight:146.1412
Molecular Formula:C6H10O4
InChIKey:ZLJAPDAAIPZOTO-JGWLITMVSA-N
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Compound Information
Molecular Weight:188.2209
Molecular Formula:C9H16O4
InChIKey:JMCCTJRPOAQYBQ-JGVFFNPUSA-N
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Compound Information
Molecular Weight:144.2114
Molecular Formula:C8H16O2
InChIKey:ABMVIHWNDWYSPT-POYBYMJQSA-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:130.1418
Molecular Formula:C6H10O3
InChIKey:NYOQQRNIGAUVDR-PBXRRBTRSA-N
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Compound Information
Molecular Weight:207.2016
Molecular Formula:C8H16O6
InChIKey:LJMHKGYFJAOPLY-BBVRLYRLSA-M
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Compound Information
Molecular Weight:118.1311
Molecular Formula:C5H10O3
InChIKey:MHGMBRBPBZPUAD-UHNVWZDZSA-N
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Compound Information
Molecular Weight:448.5491
Molecular Formula:C25H36O7
InChIKey:WTJXLEDIKJCPHC-LDTOHRHBSA-N
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Compound Information
Molecular Weight:545.817
Molecular Formula:C32H51NO4S
InChIKey:HURKPMAQQCYDMM-AJQTZOPKSA-N
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Compound Information
Molecular Weight:182.2594
Molecular Formula:C11H18O2
InChIKey:QNLDXLAPCXMDNF-UAURGBINSA-N
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Compound Information
Molecular Weight:294.816
Molecular Formula:C17H23ClO2
InChIKey:OIYRZXJDSDRVQP-YKSKLDQVSA-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:214.3443
Molecular Formula:C13H26O2
InChIKey:LGZFFGLHTVVJLY-QWHCGFSZSA-N
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Compound Information
Molecular Weight:320.4663
Molecular Formula:C20H32O3
InChIKey:VCIIHRPANCLYJM-LPXKSRHMSA-N
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Compound Information
Molecular Weight:295.397
Molecular Formula:C15H21NO3S
InChIKey:MGVSCHSGGGOSSE-AWEZNQCLSA-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:188.2209
Molecular Formula:C9H16O4
InChIKey:XVMMFQKUBRIGSX-YUMQZZPRSA-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:130.1849
Molecular Formula:C7H14O2
InChIKey:GWQYGFRJHHGOMU-VDTYLAMSSA-N
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Compound Information
Molecular Weight:126.043
Molecular Formula:Na2O3S
InChIKey:GEHJYWRUCIMESM-UHFFFAOYSA-L
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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:302.86
Molecular Formula:C15H23ClO2S
InChIKey:JAPYIBBSTJFDAK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:20.00634
Molecular Formula:FH
InChIKey:KRHYYFGTRYWZRS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:316.3038
Molecular Formula:C14H20O8
InChIKey:LWZRVLJBIMJPDY-MBNYWOFBSA-N
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Compound Information
Molecular Weight:116.11
Molecular Formula:C6H5LiS
InChIKey:HPFQTCRYSOTMDJ-UHFFFAOYSA-M
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