Standard Article

The Ramberg-Bäcklund Rearrangement

  1. Leo A. Paquette*,*

Published Online: 15 JUL 2005

DOI: 10.1002/0471264180.or025.01

Organic Reactions

Organic Reactions

How to Cite

Paquette, L. A. 2005. The Ramberg-Bäcklund Rearrangement. Organic Reactions. 25:1:1–71.

Author Information

  1. The Ohio State University, Columbus, Ohio

  1. *

    The invaluable assistance of Donna Canode and Carol Rose in the meticulous typing of this manuscript is warmly appreciated.

Publication History

  1. Published Online: 15 JUL 2005

Chemistry Terms

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Abstract

The halogen atoms of α-halo sulfones, in contrast to halogen atoms α to other electron-withdrawing functionalities, show marked resistance to substitution by external nucleophiles. Seemingly, polar, steric, and field effects combine to repel nucleophilic species. However, the same α-sulfonyl halogen atoms are capable of facile intramolecular 1,3 elimination, leading to replacement of the sulfonyl group by a carbon[BOND]carbon double bond with loss of halide and sulfite ions. This extrusion process, frequently referred to as the α-halo sulfone or Ramberg-Bäcklund rearrangement after its discoverers, has found broad utility in olefin synthesis. The reaction is generally applicable and easy to use.

Its earliest application dealt with the preparation of alkenes, the cis isomers of which predominated. Whereas such molecules may be more readily available by other methods, none of the alternative procedures offers the added option of specifically replacing the olefinic hydrogen atoms with deuterium by merely conducting the rearrangement in deuterated solvents. Moreover, because the α-halo sulfones undergo this transformation in alkaline solution, further rearrangement of the initially formed alkenes is precluded. Therefore the SO2 group in the starting sulfone is invariably replaced cleanly and unequivocally by the π bond.

The rearrangement is generally applicable to molecules containing the minimal structural requirements of a sulfonyl group, an α-halogen atom, and at least one α′-hydrogen atom, even in systems leading to small-ring cycloalkenes. Di- and tri-halo sulfones behave analogously. Conformational constraints, adverse hybridization characteristics, and excessive strain are known to deter the reaction. Inasmuch as these features arise only in special circumstances, they do not necessarily detract from its usefulness.

This chapter summarizes the more important advances in the understanding of α-halo sulfone rearrangements, particular consideration being given to the nature of the intermediates, scope of the available synthetic alternatives, optimization of experimental conditions, and effect of structural features on reactivity. Closely related transformations are also discussed.

Keywords:

  • Ramberg-Backlund rearrangement;
  • halogenation;
  • halo sulfones;
  • halo sulfides;
  • sulfonyl carbanions;
  • sulfinate salts;
  • oxidation;
  • alkylation;
  • cycloaddition;
  • halosulfenes;
  • diazo compounds;
  • scope;
  • limitations;
  • experimental procedures;
  • acyclic compounds;
  • cyclic compounds;
  • synthetic utility

Featured Compounds

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  1. 1 - 250
Compound Information
Molecular Weight:0
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:112.1696
Molecular Formula:C7H12O
InChIKey:Not Available
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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:171.013
Molecular Formula:C2H3BrO2S
InChIKey:BQBWHJRTPBLBJW-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:242.2268
Molecular Formula:C14H10O4
InChIKey:Not Available
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Compound Information
Molecular Weight:206.378
Molecular Formula:C8H18O2SSi
InChIKey:FQXAWGKFANSWHV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:154.2078
Molecular Formula:C12H10
InChIKey:Not Available
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Compound Information
Molecular Weight:58.0791
Molecular Formula:C3H6O
InChIKey:NBBJYMSMWIIQGU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:112.535
Molecular Formula:CHClO2S
InChIKey:HZFLHEQJEYCNCU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:242.808
Molecular Formula:C13H19ClS
InChIKey:MPTIZGBCFDBIPI-XQQFMLRXSA-N
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Compound Information
Molecular Weight:110.177
Molecular Formula:C6H6S
InChIKey:RMVRSNDYEFQCLF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:214.238
Molecular Formula:C9H10O4S
InChIKey:HPWAJMXOEYIERK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:244.309
Molecular Formula:C14H12O2S
InChIKey:ZXQADSQBNWPCCC-OKILXGFUSA-N
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Compound Information
Molecular Weight:231.14
Molecular Formula:C7H12Cl2O2S
InChIKey:AWPAMZIFUUFBEY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:232.727
Molecular Formula:C10H13ClO2S
InChIKey:QIIPVORITGAESW-CBMCFHRWSA-N
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Compound Information
Molecular Weight:196.266
Molecular Formula:C10H14O2S
InChIKey:SKVOHSLSOQVSIL-AOOOYVTPSA-N
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Compound Information
Molecular Weight:206.068
Molecular Formula:C4H8Cl2O3S
InChIKey:DYDYMSCHKIEBBR-UHFFFAOYSA-M
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Compound Information
Molecular Weight:334.344
Molecular Formula:C16H14O6S
InChIKey:OYOBGAMJVFCGJH-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:162.1852
Molecular Formula:C10H10O2
InChIKey:SCBUQIQXUBOQAI-YWEYNIOJSA-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:172.675
Molecular Formula:C8H9ClS
InChIKey:COVIHMADWYEBTP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:154.615
Molecular Formula:C4H7ClO2S
InChIKey:XDKZGFIHQNLWSY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:148.223
Molecular Formula:C6H12O2S
InChIKey:VSSXJBORNFGNFD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:140.2981
Molecular Formula:C8H16Si
InChIKey:ZDSFBVVBFMKMRF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:182.2574
Molecular Formula:C14H12
InChIKey:Not Available
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Compound Information
Molecular Weight:109.597
Molecular Formula:C3H6ClS
InChIKey:TWRGQWCUJSTYKH-UHFFFAOYSA-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:294.122
Molecular Formula:C8H8BrNO4S
InChIKey:BZISBERTSYOIPK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:152.1919
Molecular Formula:C12H8
InChIKey:Not Available
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Compound Information
Molecular Weight:248.771
Molecular Formula:C14H13ClS
InChIKey:GTGINHXSBJDSGK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:169.2413
Molecular Formula:C10H18O2
InChIKey:IZOFWCYKCWUJBY-SNAWJCMRSA-M
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Compound Information
Molecular Weight:196.266
Molecular Formula:C10H12O2S
InChIKey:QZPWQGGLEGVANR-AOOOYVTPSA-N
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Compound Information
Molecular Weight:102.1332
Molecular Formula:C8H6
InChIKey:UEXCJVNBTNXOEH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:58.1186
Molecular Formula:C4H8
InChIKey:Not Available
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Compound Information
Molecular Weight:297.209
Molecular Formula:C10H17BrO3S
InChIKey:GZZWGYYCDZSJOW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:106.165
Molecular Formula:C8H10
InChIKey:WTQBISBWKRKLIJ-YUMQZZPRSA-N
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Compound Information
Molecular Weight:287.591
Molecular Formula:C9H9Cl3O2S
InChIKey:GVKAWKLVAZJKMF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:166.647
Molecular Formula:C10H11Cl
InChIKey:UAWVSMAPCUGUAL-WEVVVXLNSA-N
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Compound Information
Molecular Weight:307.161
Molecular Formula:C10H11BrO4S
InChIKey:MENQYAXTRAMZKF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:134.97
Molecular Formula:Cl2O2S
InChIKey:YBBRCQOCSYXUOC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:198.282
Molecular Formula:C10H14O2S
InChIKey:CVBJAUACQDKUTC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:133.533
Molecular Formula:C4H4ClNO2
InChIKey:JRNVZBWKYDBUCA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:204.287
Molecular Formula:C9H16O3S
InChIKey:XCTQAWQDXBWPAD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:171.623
Molecular Formula:C4H9ClO3S
InChIKey:RHEZXBUIIQYQFP-UHFFFAOYSA-M
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Compound Information
Molecular Weight:148.996
Molecular Formula:CH2Cl2O2S
InChIKey:KQDDQXNVESLJNO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:153.823
Molecular Formula:CCl4
InChIKey:VZGDMQKNWNREIO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:64.055
Molecular Formula:C4H9Li
InChIKey:BKDLGMUIXWPYGD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:70.906
Molecular Formula:Cl2
InChIKey:KZBUYRJDOAKODT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:194.679
Molecular Formula:C7H11ClO2S
InChIKey:PIJUUXAVMLNFFU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:277.178
Molecular Formula:C10H13BrO2S
InChIKey:KHCRDLVPLFGTCI-UHFFFAOYSA-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:225.521
Molecular Formula:C4H7Cl3O2S
InChIKey:BQEQCZFMQCAOIQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:196.266
Molecular Formula:C10H12O2S
InChIKey:VSAQDMZGAANHEQ-UHFFFAOYSA-N
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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:146.207
Molecular Formula:C6H10O2S
InChIKey:OGBZCZYBRFUKKO-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:80.912
Molecular Formula:BrH
InChIKey:CPELXLSAUQHCOX-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:177.082
Molecular Formula:C7H13Br
InChIKey:UUWSLBWDFJMSFP-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:194.679
Molecular Formula:C7H11ClO2S
InChIKey:GDHNHWPWCAIITP-RQJHMYQMSA-N
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Compound Information
Molecular Weight:144.192
Molecular Formula:C6H8O2S
InChIKey:MDXLNBPNUBORAI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:191.076
Molecular Formula:C4H8Cl2O2S
InChIKey:YCJARYOIQSUHKE-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:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:120.17
Molecular Formula:C4H8O2S
InChIKey:FAXAWLXXQOPCQN-ZXZARUISSA-N
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Compound Information
Molecular Weight:138.23
Molecular Formula:C8H10S
InChIKey:OFQPKKGMNWASPN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:132.2023
Molecular Formula:C10H12
InChIKey:ZJUKRBUQLPNVRK-AOOOYVTPSA-N
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Compound Information
Molecular Weight:177.714
Molecular Formula:C8H14ClS
InChIKey:YUVBZWJHYOKLJQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:90.551
Molecular Formula:C4H7Cl
InChIKey:KWISWUFGPUHDRY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:194.2717
Molecular Formula:C15H14
InChIKey:OVZXISBUYCEVEV-OUKQBFOZSA-N
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Compound Information
Molecular Weight:134.197
Molecular Formula:C5H10O2S
InChIKey:ZCHLRRRUQBMXCE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:322.163
Molecular Formula:C10H11IO2S
InChIKey:VGBLLWFNZWDSBZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:233.586
Molecular Formula:C7H11Cl3S
InChIKey:AIQGESAGACIDEL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:30.026
Molecular Formula:CH2O
InChIKey:Not Available
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Compound Information
Molecular Weight:183.205
Molecular Formula:C8H8O3S
InChIKey:AGBXYHCHUYARJY-VOTSOKGWSA-M
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Compound Information
Molecular Weight:60.052
Molecular Formula:C2H4O2
InChIKey:QTBSBXVTEAMEQO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:283.183
Molecular Formula:C9H15BrO3S
InChIKey:HKAOGMSWGTWYAW-UHFFFAOYSA-N
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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:228.781
Molecular Formula:C12H17ClS
InChIKey:PHRRYFMMXUABOI-SDDRHHMPSA-N
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Compound Information
Molecular Weight:96.1702
Molecular Formula:C7H12
InChIKey:YULMNMJFAZWLLN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:172.675
Molecular Formula:C8H9ClS
InChIKey:UMFDSFPDTLREFS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:212.31
Molecular Formula:C14H12S
InChIKey:CKRHZOWPBLGADU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:185.04
Molecular Formula:C3H5BrO2S
InChIKey:WWPUFFUIOTWPPO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:183.205
Molecular Formula:C8H8O3S
InChIKey:STQQXKVBEVTXDO-UHFFFAOYSA-M
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Compound Information
Molecular Weight:404.117
Molecular Formula:C14H12Br2O2S
InChIKey:SSUJZTMQDMLCDT-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:258.335
Molecular Formula:C15H14O2S
InChIKey:MRTIWTGAGMZREP-VAWYXSNFSA-N
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Compound Information
Molecular Weight:267.172
Molecular Formula:C10H12Cl2O2S
InChIKey:ZIBHAUMLVVPUCR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:76.161
Molecular Formula:C3H8S
InChIKey:SUVIGLJNEAMWEG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:208.363
Molecular Formula:C13H20S
InChIKey:CQTVTODWIPVXFA-BETUJISGSA-N
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Compound Information
Molecular Weight:130.1864
Molecular Formula:C10H10
InChIKey:Not Available
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Compound Information
Molecular Weight:138.23
Molecular Formula:C8H10S
InChIKey:AGFYZLVFPSGUIX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:74.1216
Molecular Formula:C4H10O
InChIKey:RTZKZFJDLAIYFH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:226.766
Molecular Formula:C12H15ClS
InChIKey:ZAYJNZJIPKNXQA-GRYCIOLGSA-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:124.203
Molecular Formula:C7H8S
InChIKey:UENWRTRMUIOCKN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:202.314
Molecular Formula:C10H18O2S
InChIKey:FBHUMXQAXIGCHH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:258.764
Molecular Formula:C12H15ClO2S
InChIKey:BWNCZALTXQSFOM-YOGCLGLASA-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:258.743
Molecular Formula:C7H11ClO4S2
InChIKey:JADCSFWGUFLRRY-RNFRBKRXSA-N
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Compound Information
Molecular Weight:198.219
Molecular Formula:C8H9NO3S
InChIKey:YDQNDKBOOVXRTL-UHFFFAOYSA-M
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Compound Information
Molecular Weight:132.2023
Molecular Formula:C10H12
InChIKey:UHBCMPKTYJDESJ-AOOOYVTPSA-N
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Compound Information
Molecular Weight:278.754
Molecular Formula:C14H11ClO2S
InChIKey:RQTYMFKODZNEEK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:208.2982
Molecular Formula:C16H16
InChIKey:JHLNLKYQTWQERE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:160.234
Molecular Formula:C7H12O2S
InChIKey:KUISSOFALBJOHY-KNVOCYPGSA-N
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Compound Information
Molecular Weight:333.252
Molecular Formula:C10H14Cl2O4S2
InChIKey:UFUAXFDBRYUPFV-OXYCZDQYSA-N
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Compound Information
Molecular Weight:142.262
Molecular Formula:C8H14S
InChIKey:PXIVTQKYHYIJES-UHFFFAOYSA-N
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Compound Information
Molecular Weight:196.695
Molecular Formula:C7H13ClO2S
InChIKey:JKLHQDFTZLNOTH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:155.194
Molecular Formula:C7H8O2S
InChIKey:FXJVNINSOKCNJP-UHFFFAOYSA-M
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Compound Information
Molecular Weight:207.474
Molecular Formula:C2H4BrClO2S
InChIKey:YNDSPGGGVZYKHL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:232.727
Molecular Formula:C10H13ClO2S
InChIKey:PGYMHWHBBBQCOG-BBBLOLIVSA-N
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Compound Information
Molecular Weight:185.04
Molecular Formula:C3H5BrO2S
InChIKey:BSTQPTBGKBZMQT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:227.773
Molecular Formula:C12H16ClS
InChIKey:VJTNWZKPYGELGW-IMRBUKKESA-N
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Compound Information
Molecular Weight:237.048
Molecular Formula:C7H9BrO4
InChIKey:XCOQDRFRYIKEMS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:242.808
Molecular Formula:C13H19ClS
InChIKey:KJMIYVZTKNXBKQ-RWMBFGLXSA-N
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Compound Information
Molecular Weight:176.707
Molecular Formula:C8H13ClS
InChIKey:PXLBSVKTYXBNRN-UPHRSURJSA-N
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Compound Information
Molecular Weight:68.117
Molecular Formula:C5H8
InChIKey:LPIQUOYDBNQMRZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:158.2396
Molecular Formula:C12H14
InChIKey:VGWHURSVJWSFCK-TXEJJXNPSA-N
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Compound Information
Molecular Weight:211.687
Molecular Formula:C7H13ClO3S
InChIKey:UBJNUXFWPUWGKE-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:66.1011
Molecular Formula:C5H6
InChIKey:ZSWFCLXCOIISFI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:166.283
Molecular Formula:C10H14S
InChIKey:JBOBEQWDLMOEMF-AOOOYVTPSA-N
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Compound Information
Molecular Weight:180.652
Molecular Formula:C6H9ClO2S
InChIKey:MZMJFPLLRRTPAD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:124.996
Molecular Formula:C4H6Cl2
InChIKey:GSQMUEGXIDQJES-UHFFFAOYSA-N
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Compound Information
Molecular Weight:176.707
Molecular Formula:C8H13ClS
InChIKey:XIEMXLXHYAFHSL-CSMHCCOUSA-N
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Compound Information
Molecular Weight:240.792
Molecular Formula:C13H17ClS
InChIKey:OUXQWLNXNGGIDC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:54.0904
Molecular Formula:C4H6
InChIKey:KAKZBPTYRLMSJV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:215.098
Molecular Formula:C6H8Cl2O2S
InChIKey:LEYOXMLEUJOPNO-UHFFFAOYSA-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:281.2
Molecular Formula:C14H10Cl2S
InChIKey:ODCQSNGOFMCNHQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:247.699
Molecular Formula:C9H10ClNO3S
InChIKey:KYECLOYRQLKHFU-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:207.12
Molecular Formula:C8H8Cl2S
InChIKey:VWMPTZKLUNBUKF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:42.04
Molecular Formula:CH2N2
InChIKey:YXHKONLOYHBTNS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:239.13
Molecular Formula:C7H11BrO2S
InChIKey:GFHABJQRBGMJQB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:373.018
Molecular Formula:C8H7Br2NO4S
InChIKey:BPHPMVLHSZDELY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:140.2981
Molecular Formula:C8H16Si
InChIKey:DFUKTQBHAVKKRS-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:164.696
Molecular Formula:C7H13ClS
InChIKey:UAWFPBICPLHLCY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:200.728
Molecular Formula:C10H13ClS
InChIKey:AKDMZKOIZZDDSP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:150.241
Molecular Formula:C9H10S
InChIKey:ZZQUQFZVCJWSER-UHFFFAOYSA-N
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Compound Information
Molecular Weight:191.076
Molecular Formula:C4H8Cl2O2S
InChIKey:YRABFLMUDIWCMG-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:169.083
Molecular Formula:C4H9BrS
InChIKey:NWHAKFYYXZJSGG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:251.141
Molecular Formula:C8H11BrO2S
InChIKey:DWVRUKMYMAMGAZ-KVARREAHSA-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: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:34.081
Molecular Formula:H2S
InChIKey:RWSOTUBLDIXVET-UHFFFAOYSA-N
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Compound Information
Molecular Weight:105.921
Molecular Formula:CBrN
InChIKey:ATDGTVJJHBUTRL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:281.2
Molecular Formula:C14H10Cl2S
InChIKey:MMIIHJLUWIXBBB-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:177.984
Molecular Formula:C4H4BrNO2
InChIKey:PCLIMKBDDGJMGD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:262.798
Molecular Formula:C15H15ClS
InChIKey:KDOHTUBKQAYLNU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:213.093
Molecular Formula:C5H9BrO2S
InChIKey:FRGXZNSXVNPXIG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:260.351
Molecular Formula:C15H16O2S
InChIKey:LKLLTIFICUJZKE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:184.686
Molecular Formula:C9H9ClS
InChIKey:KKGJBLUUVUFZMA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:108.567
Molecular Formula:C4H9ClO
InChIKey:IXZDIALLLMRYOU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:283.216
Molecular Formula:C14H12Cl2S
InChIKey:GKOZSPYHGLRQTD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:224.9845
Molecular Formula:C4H4INO2
InChIKey:LQZMLBORDGWNPD-UHFFFAOYSA-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:78.1118
Molecular Formula:C6H6
InChIKey:UHOVQNZJYSORNB-UHFFFAOYSA-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:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:328.021
Molecular Formula:C8H8Br2O2S
InChIKey:JFXRNMIMRDDPLD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:159.808
Molecular Formula:Br2
InChIKey:GDTBXPJZTBHREO-UHFFFAOYSA-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:180.2415
Molecular Formula:C14H10
InChIKey:Not Available
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Compound Information
Molecular Weight:136.17
Molecular Formula:C4H8O3S
InChIKey:TZHSPTPGMNEBNA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:75.1278
Molecular Formula:C4H10O
InChIKey:Not Available
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Compound Information
Molecular Weight:239.119
Molecular Formula:C8H8Cl2O2S
InChIKey:WNQPRQUEWVJERO-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:81.071
Molecular Formula:H2O3S
InChIKey:LSNNMFCWUKXFEE-UHFFFAOYSA-M
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Compound Information
Molecular Weight:218.313
Molecular Formula:C10H18O3S
InChIKey:MSMXZUHZRKTDJW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:178.251
Molecular Formula:C10H10OS
InChIKey:RGGMMNLHJPLYKR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:136.234
Molecular Formula:C10H16
InChIKey:UBFBTMRIJJRZOA-AATRIKPKSA-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:126.562
Molecular Formula:C2H3ClO2S
InChIKey:KYLJOEYGEVFAFF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:403.311
Molecular Formula:C15H15BrO4S2
InChIKey:CNWHMJWKWKYBQE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:104.1491
Molecular Formula:C8H8
InChIKey:PPBRXRYQALVLMV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:194.336
Molecular Formula:C12H18S
InChIKey:LPZHLGIDTACMCQ-TXEJJXNPSA-N
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Compound Information
Molecular Weight:148.225
Molecular Formula:C9H8S
InChIKey:Not Available
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Compound Information
Molecular Weight:240.276
Molecular Formula:C11H12O4S
InChIKey:UPBFPFYEXBXETO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:314.217
Molecular Formula:C10H19BrO4S
InChIKey:AYMALHXXIRUKHY-UHFFFAOYSA-M
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Compound Information
Molecular Weight:378.08
Molecular Formula:C12H10Br2O2S
InChIKey:PVBSAZRACDWLQX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:130.615
Molecular Formula:C7H11Cl
InChIKey:JIXIAHPDXXKGTP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:274.378
Molecular Formula:C16H18O2S
InChIKey:KZCDKECACHXKSV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:128.942
Molecular Formula:C2H2Cl2O2
InChIKey:JXTHNDFMNIQAHM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:84.1595
Molecular Formula:C6H12
InChIKey:Not Available
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Compound Information
Molecular Weight:213.093
Molecular Formula:C5H9BrO2S
InChIKey:ASPGGZLLTUXFLN-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:283.216
Molecular Formula:C14H12Cl2S
InChIKey:FVOVHSWEQKCUES-UHFFFAOYSA-N
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Compound Information
Molecular Weight:228.781
Molecular Formula:C12H17ClS
InChIKey:PHRRYFMMXUABOI-GRYCIOLGSA-N
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Compound Information
Molecular Weight:242.808
Molecular Formula:C13H19ClS
InChIKey:MPTIZGBCFDBIPI-UPJWGTAASA-N
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Compound Information
Molecular Weight:227.773
Molecular Formula:C12H16ClS
InChIKey:VJTNWZKPYGELGW-DABQJJPHSA-N
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Compound Information
Molecular Weight:141.253
Molecular Formula:C8H14S
InChIKey:MZZYOZGXMWGIMM-SFYZADRCSA-N
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Compound Information
Molecular Weight:141.253
Molecular Formula:C8H14S
InChIKey:MZZYOZGXMWGIMM-SFYZADRCSA-N
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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:262.798
Molecular Formula:C15H15ClS
InChIKey:ZQGXYYFNJPJTKQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:232.727
Molecular Formula:C10H13ClO2S
InChIKey:PGYMHWHBBBQCOG-AEJSXWLSSA-N
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Compound Information
Molecular Weight:146.207
Molecular Formula:C6H10O2S
InChIKey:RYENSCWXGSYRMD-OLQVQODUSA-N
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Compound Information
Molecular Weight:225.103
Molecular Formula:C6H9BrO2S
InChIKey:QSBVUCBDLQZUKT-OLQVQODUSA-N
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Compound Information
Molecular Weight:56.1063
Molecular Formula:C4H8
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:33.048
Molecular Formula:CH4O
InChIKey:Not Available
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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:232.727
Molecular Formula:C10H13ClO2S
InChIKey:PGYMHWHBBBQCOG-XVBQNVSMSA-N
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Compound Information
Molecular Weight:259.77
Molecular Formula:C12H15ClO2S
InChIKey:Not Available
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Compound Information
Molecular Weight:261.783
Molecular Formula:C12H15ClO2S
InChIKey:Not Available
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Compound Information
Molecular Weight:160.2519
Molecular Formula:C12H14
InChIKey:Not Available
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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:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:236.2653
Molecular Formula:C16H12O2
InChIKey:WYCXGQSQHAXLPK-VAWYXSNFSA-N
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Compound Information
Molecular Weight:234.3355
Molecular Formula:C18H18
InChIKey:XLGTYGXQYKXRNG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:266.311
Molecular Formula:C10H18O6S
InChIKey:BMICYSBNEWJRDP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:202.314
Molecular Formula:C10H18O2S
InChIKey:FVNOBOJNBYUMMH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:184.255
Molecular Formula:C9H12O2S
InChIKey:QXFZZULXEGYJJE-SPJNRGJMSA-N
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Compound Information
Molecular Weight:248.726
Molecular Formula:C10H13ClO3S
InChIKey:WMACVMWCJDQASA-CBMCFHRWSA-N
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Compound Information
Molecular Weight:74.1216
Molecular Formula:C4H10O
InChIKey:LRHPLDYGYMQRHN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:205.2545
Molecular Formula:C15H11N
InChIKey:NQUFFEOQBCAXSM-WGEIWTTOSA-N
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Compound Information
Molecular Weight:299.184
Molecular Formula:C12H11BrO2S
InChIKey:WCORRPYOVISRAN-QEWOUOOISA-N
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Compound Information
Molecular Weight:76.0944
Molecular Formula:C3H8O2
InChIKey:NKDDWNXOKDWJAK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:215.109
Molecular Formula:C5H11BrO2S
InChIKey:RHKVZNQNPIOTKZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:80.1277
Molecular Formula:C6H8
InChIKey:YWDBHFZUBPOPRQ-OLQVQODUSA-N
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Compound Information
Molecular Weight:248.726
Molecular Formula:C10H13ClO3S
InChIKey:HLJSJHBZPZPARS-CBMCFHRWSA-N
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Compound Information
Molecular Weight:70.1329
Molecular Formula:C5H10
InChIKey:MHNNAWXXUZQSNM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:149.189
Molecular Formula:C5H10O3S
InChIKey:BIYCHPUIIDCAPR-SNAWJCMRSA-M
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Compound Information
Molecular Weight:397.283
Molecular Formula:C17H17BrO4S
InChIKey:BYKVRRJLCIHNQZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:198.282
Molecular Formula:C10H14O2S
InChIKey:DUFIQZPRYPNQDC-AOOOYVTPSA-N
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Compound Information
Molecular Weight:254.733
Molecular Formula:C12H11ClO2S
InChIKey:HQZKPSYGFOOOFX-UTUOFQBUSA-N
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Compound Information
Molecular Weight:232.727
Molecular Formula:C10H13ClO2S
InChIKey:QIIPVORITGAESW-XVBQNVSMSA-N
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Compound Information
Molecular Weight:232.3196
Molecular Formula:C18H16
InChIKey:SHCAFRNIXFPCQX-IYARVYRRSA-N
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Compound Information
Molecular Weight:288.403
Molecular Formula:C14H24O4S
InChIKey:RRPGGAYWURUIOJ-WLPIGLKUSA-N
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Compound Information
Molecular Weight:291.162
Molecular Formula:C10H11BrO3S
InChIKey:HOYGYPPEGTVVGH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:114.1424
Molecular Formula:C6H10O2
InChIKey:XXHDAWYDNSXJQM-ONEGZZNKSA-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:300.415
Molecular Formula:C18H20O2S
InChIKey:BXOZNDMXFXFSHH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:259.118
Molecular Formula:C6H11BrO4S
InChIKey:UZWMDTOXAGFPIJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:148.1586
Molecular Formula:C9H8O2
InChIKey:WBYWAXJHAXSJNI-SREVYHEPSA-N
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Compound Information
Molecular Weight:150.2176
Molecular Formula:C10H14O
InChIKey:JKRPIYKMBITSBI-AOOOYVTPSA-N
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Compound Information
Molecular Weight:258.764
Molecular Formula:C12H15ClO2S
InChIKey:GPAIKHSCWSQBTK-GLXQMMQGSA-N
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Compound Information
Molecular Weight:301.469
Molecular Formula:C17H19NS2
InChIKey:LLTGNJNDMFUXSS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:307.161
Molecular Formula:C10H11BrO4S
InChIKey:RFRPTIWNSQNAPK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:321.188
Molecular Formula:C11H13BrO4S
InChIKey:KZMQTPKWWUTMIV-UHFFFAOYSA-N
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