Standard Article

The Pummerer Reaction of Sulfinyl Compounds

  1. Ottorino de Lucchi1,
  2. Umberto Miotti2,
  3. Giorgio Modena2

Published Online: 15 OCT 2004

DOI: 10.1002/0471264180.or040.03

Organic Reactions

Organic Reactions

How to Cite

de Lucchi, O., Miotti, U. and Modena, G. 2004. The Pummerer Reaction of Sulfinyl Compounds. Organic Reactions. 40:3:157–405.

Author Information

  1. 1

    Dipartimento di Chimica dell'Universitá, Sassari, Italy

  2. 2

    Centro Studi Meccanismi di Reazioni Organiche del C.N.R., Dipartimento di Chimica Organica dell'Universitá, Padova, Italy

Publication History

  1. Published Online: 15 OCT 2004

Chemistry Terms

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Abstract

The Pummerer reaction involves the formation of an α-functionalized sulfide from a sulfoxide bearing at least one α-hydrogen atom. The reaction can also be described as an internal redox process where the S[DOUBLE BOND]X group is reduced and the α carbon is oxidized.

The first report by Pummerer on the reaction which now bears his name appeared in 1909 and described the formation of thiophenol and glyoxylic acid on heating phenylsulfinylacetic acid with mineral acids. The products Pummerer observed resulted from hydrolysis of the initially formed α-substituted sulfides, which are the typical products of the reaction. The term “Pummerer reaction” was later extended to the reaction of sulfoxides with acid anhydrides.

Selenium and nitrogen analogs undergo similar reactions. The former is known as the seleno–Pummerer reaction, and the latter is usually referred to as the Polonovski reaction. The sila–Pummerer reaction, which is also discussed in this chapter, is the rearrangement of sulfoxides bearing a silyl group on the α carbon.

From a mechanistic point of view there are many other reactions, sometimes given specific names, such as the Sommelet–Hauser, Stevens, and Vilsmeier rearrangements, that appear to resemble the Pummerer reaction. Reactions in which the sulfoxide group acts as an oxidant in an intermolecular redox process have characteristics similar to the typical Pummerer reaction. The α-halogenation of sulfides, in which the sulfide sulfur may first be oxidized to a halosulfonium salt that rearranges to the final product, is formally similar to the Pummerer reaction.

For the sake of clarity and to be as exhaustive as possible, we have limited the scope of this chapter to the restrictive definition.

Keywords:

  • Pummerer reaction;
  • sulfinyl compounds;
  • mechanisms;
  • synthetic applications;
  • alpha-functionalized sulfides;
  • carbonyl compounds;
  • thiols;
  • vinyl sulfides;
  • Penicillin;
  • cephalosporin;
  • natural products;
  • Sleno-Plummerer reaction;
  • Sila Pummerer reaction;
  • vinylogous reaction;
  • additive reaction;
  • nucleophiles;
  • sulfoxides;
  • scope;
  • limitations;
  • experimental procedures

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:182.1335
Molecular Formula:C7H6N2O4
InChIKey:NORABPMBUQMZLT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:119.378
Molecular Formula:CHCl3
InChIKey:HEDRZPFGACZZDS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:378.466
Molecular Formula:C17H18N2O4S2
InChIKey:XHZPBNMPCBRBNV-INIZCTEOSA-N
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Compound Information
Molecular Weight:160.277
Molecular Formula:C8H16OS
InChIKey:CMOIWROGYQTXNN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:212.2439
Molecular Formula:C14H12O2
InChIKey:PYHXGXCGESYPCW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:214.348
Molecular Formula:C10H14OS2
InChIKey:VNWFGHMTHSMPRJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:137.018
Molecular Formula:C4H9Br
InChIKey:Not Available
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Compound Information
Molecular Weight:167.1189
Molecular Formula:C7H5NO4
InChIKey:Not Available
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Compound Information
Molecular Weight:239.2246
Molecular Formula:C11H13NO5
InChIKey:GNIDSOFZAKMQAO-VIFPVBQESA-N
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Compound Information
Molecular Weight:362.488
Molecular Formula:C13H18N2O4S3
InChIKey:DYUFADZLOGQGCH-LBPRGKRZSA-N
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Compound Information
Molecular Weight:108.1378
Molecular Formula:C7H8O
InChIKey:Not Available
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Compound Information
Molecular Weight:160.234
Molecular Formula:C7H12O2S
InChIKey:NAVDIEWKCQRMNM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:184.2753
Molecular Formula:C11H20O2
InChIKey:FRPZMMHWLSIFAZ-UHFFFAOYSA-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:266.337
Molecular Formula:C6HCl5O
InChIKey:IZUPBVBPLAPZRR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:220.3505
Molecular Formula:C15H24O
InChIKey:LKFLFUALEFBQSU-CDFKWJNJSA-N
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Compound Information
Molecular Weight:178.206
Molecular Formula:C6H10O4S
InChIKey:YGBAJPRXOODRBG-SRQIZXRXSA-N
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Compound Information
Molecular Weight:178.272
Molecular Formula:C6H10O2S2
InChIKey:BWPIGFCMTMAMFQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:182.24
Molecular Formula:C9H10O2S
InChIKey:OIKCBTMOZAMVLS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:152.1473
Molecular Formula:C8H8O3
InChIKey:Not Available
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Compound Information
Molecular Weight:268.289
Molecular Formula:C11H12N2O4S
InChIKey:FHVWQQUQRBRFCF-JTQLQIEISA-N
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Compound Information
Molecular Weight:186.167
Molecular Formula:C4H11O4PS
InChIKey:HVQSWUWTKXMPDF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:232.32
Molecular Formula:C9H12O3S2
InChIKey:UPQRJRIBBYXLLC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:174.142
Molecular Formula:C4H5F3O2S
InChIKey:UVLUHGDKRZRCDF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:223.2252
Molecular Formula:C11H13NO4
InChIKey:TYRGLVWXHJRKMT-QMMMGPOBSA-N
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Compound Information
Molecular Weight:253.317
Molecular Formula:C12H15NO3S
InChIKey:QNFJEGLBSURUBZ-NSHDSACASA-N
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Compound Information
Molecular Weight:138.252
Molecular Formula:C4H10OS2
InChIKey:FIWQKOIUXFENIV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:182.283
Molecular Formula:C10H14OS
InChIKey:UEKWZVJEJNRKNJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:134.24
Molecular Formula:C6H14OS
InChIKey:SNINRXCUMRCRPE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:283.343
Molecular Formula:C13H17NO4S
InChIKey:JZJCJKQQMSYGPF-JTQLQIEISA-N
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Compound Information
Molecular Weight:320.402
Molecular Formula:C14H24O6S
InChIKey:OVWWJEZVSROOQY-PUHVVEEASA-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:325.423
Molecular Formula:C16H23NO4S
InChIKey:UKAQTYSIVCLLJP-ZDUSSCGKSA-N
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Compound Information
Molecular Weight:204.612
Molecular Formula:C4H10ClO3PS
InChIKey:NYKZNEUFHGAOBA-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:357.384
Molecular Formula:C17H15N3O4S
InChIKey:AAXSPOGLNANSNY-INIZCTEOSA-N
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Compound Information
Molecular Weight:225.264
Molecular Formula:C10H11NO3S
InChIKey:UMKUQFYUVXYMIM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:260.2836
Molecular Formula:C12H20O6
InChIKey:NFHXOQDPQIQPKT-XBWDGYHZSA-N
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Compound Information
Molecular Weight:328.407
Molecular Formula:C13H16N2O4S2
InChIKey:LKWKRVWJSVPWCH-LBPRGKRZSA-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:212.265
Molecular Formula:C10H12O3S
InChIKey:HPFZAVSEVOURRY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:89.179
Molecular Formula:C4H8S
InChIKey:RAOIDOHSFRTOEL-UHFFFAOYSA-O
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Compound Information
Molecular Weight:190.346
Molecular Formula:C10H22OS
InChIKey:OSDYLRFKXGYOIK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:162.207
Molecular Formula:C6H10O3S
InChIKey:SEYJDVWMSAZHFG-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:282.175
Molecular Formula:C6H10F3O5PS
InChIKey:QCKGSUXOQABVEV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:244.393
Molecular Formula:C13H24O2S
InChIKey:MIPAFVAUHNZMKM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:228.203
Molecular Formula:C6H13O5PS
InChIKey:WBOUROXHLNQFJL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:256.278
Molecular Formula:C10H12N2O4S
InChIKey:SBUQMRSYODPSHI-ZHACJKMWSA-N
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Compound Information
Molecular Weight:326.368
Molecular Formula:C14H18N2O5S
InChIKey:FSUOVEGOOPPDKH-NSHDSACASA-N
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Compound Information
Molecular Weight:258.4292
Molecular Formula:C13H26O3Si
InChIKey:POTVAPXKASPNAL-CHWSQXEVSA-N
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Compound Information
Molecular Weight:359.439
Molecular Formula:C19H21NO4S
InChIKey:GYAKZYUZLBFTDT-KRWDZBQOSA-N
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Compound Information
Molecular Weight:344.382
Molecular Formula:C18H16O5S
InChIKey:DRVDDDBOXHYOOW-HZPDHXFCSA-N
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Compound Information
Molecular Weight:163.1302
Molecular Formula:C8H5NO3
InChIKey:Not Available
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Compound Information
Molecular Weight:216.685
Molecular Formula:C9H9ClO2S
InChIKey:OPIXEYUEPYFAKJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:138.185
Molecular Formula:C4H10O3S
InChIKey:XHKPPUVICXLDRJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:100.1589
Molecular Formula:C6H12O
InChIKey:ZCHHRLHTBGRGOT-SNAWJCMRSA-N
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Compound Information
Molecular Weight:398.475
Molecular Formula:C21H22N2O4S
InChIKey:YYXJVADPUJYZPO-IBGZPJMESA-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:343.462
Molecular Formula:C15H21NO4S2
InChIKey:KJAGWHCKUWCBDP-ZDUSSCGKSA-N
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Compound Information
Molecular Weight:222.069
Molecular Formula:C10H11BO3S
InChIKey:QGWGJCNPXDIJAE-WYPFBEBGSA-N
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Compound Information
Molecular Weight:198.327
Molecular Formula:C5H10O2S3
InChIKey:OYWLSGKFOFACAU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:212.265
Molecular Formula:C10H12O3S
InChIKey:KRCFDXCLYDVSHT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:223.248
Molecular Formula:C10H9NO3S
InChIKey:MQQJLEUDWQYOGJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:212.352
Molecular Formula:C12H20OS
InChIKey:FFQYCOMJUXSSDP-MNOVXSKESA-N
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Compound Information
Molecular Weight:182.283
Molecular Formula:C10H14OS
InChIKey:IIQFMHFUFAUVEA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:266.25
Molecular Formula:C12H14N2O5
InChIKey:Not Available
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Compound Information
Molecular Weight:84.0066
Molecular Formula:CHNaO3
InChIKey:UIIMBOGNXHQVGW-UHFFFAOYSA-M
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Compound Information
Molecular Weight:148.223
Molecular Formula:C6H12O2S
InChIKey:UWWQAJDVCDRHHP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:265.305
Molecular Formula:C14H19NO4
InChIKey:ZYJPUMXJBDHSIF-NSHDSACASA-N
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Compound Information
Molecular Weight:158.261
Molecular Formula:C8H14OS
InChIKey:LTOLLBPTRNSRBD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:341.423
Molecular Formula:C16H23NO5S
InChIKey:TUMJZCMNUAKQRD-ZDUSSCGKSA-N
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Compound Information
Molecular Weight:174.304
Molecular Formula:C9H18OS
InChIKey:IZSGEWCPEZHIGH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:114.0233
Molecular Formula:C2HF3O2
InChIKey:DTQVDTLACAAQTR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:108.159
Molecular Formula:C3H8O2S
InChIKey:XMSRCWAGWXZRRT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:280.469
Molecular Formula:C17H28OS
InChIKey:UADPYRPOGTWTIM-PZJKJEQHSA-N
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Compound Information
Molecular Weight:216.383
Molecular Formula:C12H24OS
InChIKey:UGAXJTPAJDYMCD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:302.37
Molecular Formula:C11H14N2O4S2
InChIKey:IEPGPGYHPGUUBZ-JTQLQIEISA-N
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Compound Information
Molecular Weight:176.32
Molecular Formula:C9H20OS
InChIKey:HREBQLCXYQHWLD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:114.1855
Molecular Formula:C7H14O
InChIKey:VTBOTOBFGSVRMA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:200.033
Molecular Formula:C7H6BrNO
InChIKey:UIIZGAXKZZRCBN-WEVVVXLNSA-N
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Compound Information
Molecular Weight:94.1112
Molecular Formula:C6H6O
InChIKey:ISWSIDIOOBJBQZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:178.272
Molecular Formula:C6H10O2S2
InChIKey:JLDAPQJZDDNMDW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:122.1644
Molecular Formula:C8H10O
InChIKey:WRMNZCZEMHIOCP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:467.622
Molecular Formula:C30H29NO2S
InChIKey:ZSDSHSVSPHXHPV-NDEPHWFRSA-N
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Compound Information
Molecular Weight:281.3044
Molecular Formula:C14H19NO5
InChIKey:CNBUSIJNWNXLQQ-NSHDSACASA-N
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Compound Information
Molecular Weight:228.225
Molecular Formula:C8H8N2O4S
InChIKey:YHLZIVPYFSFLNI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:141.928
Molecular Formula:C4H10BF3O
InChIKey:MZTVMRUDEFSYGQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:236.308
Molecular Formula:C8H12O4S2
InChIKey:SSFMFLXTPJWZFE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:106.187
Molecular Formula:C4H10OS
InChIKey:WOBARLJSXVAEGX-UHFFFAOYSA-N
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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:230.3761
Molecular Formula:C11H22O3Si
InChIKey:MUPHNLAMZYHISA-GHMZBOCLSA-N
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Compound Information
Molecular Weight:338.3572
Molecular Formula:C19H18N2O4
InChIKey:Not Available
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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:18.0153
Molecular Formula:H2O
InChIKey:XLYOFNOQVPJJNP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:158.175
Molecular Formula:C6H6O3S
InChIKey:SRSXLGNVWSONIS-UHFFFAOYSA-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:318.547
Molecular Formula:C15H30O3SSi
InChIKey:VNLLQNNSUSJAQC-HUUCEWRRSA-N
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Compound Information
Molecular Weight:299.343
Molecular Formula:C13H17NO5S
InChIKey:ZXUFRBCRGXHEQZ-NSHDSACASA-N
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Compound Information
Molecular Weight:196.1601
Molecular Formula:C8H8N2O4
InChIKey:HIJYJXGWKHLZPA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:146.207
Molecular Formula:C6H10O2S
InChIKey:IFEXAEIVIOYZDX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:172.202
Molecular Formula:C7H8O3S
InChIKey:JOXIMZWYDAKGHI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:206.3272
Molecular Formula:C13H22N2
InChIKey:QOSSAOTZNIDXMA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:212.33
Molecular Formula:C7H16O3S2
InChIKey:LBQNYGOIYZWPIW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:261.1972
Molecular Formula:C11H10F3NO3
InChIKey:WVHMOENDFIKQBZ-QMMMGPOBSA-N
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Compound Information
Molecular Weight:102.0886
Molecular Formula:C4H6O3
InChIKey:Not Available
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Compound Information
Molecular Weight:509.571
Molecular Formula:C27H27NO7S
InChIKey:KVFXLOQVUXSZJI-DEOSSOPVSA-N
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Compound Information
Molecular Weight:106.187
Molecular Formula:C4H10OS
InChIKey:KBGDIHYLFZNUNL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:417.502
Molecular Formula:C19H19N3O4S2
InChIKey:HDMIMDRZJZXQGM-SFHVURJKSA-N
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Compound Information
Molecular Weight:130.2279
Molecular Formula:C8H18O
InChIKey:Not Available
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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:162.164
Molecular Formula:C5H6O4S
InChIKey:DXRFKRUHRSOBFI-ZDBZNMESSA-N
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Compound Information
Molecular Weight:102.155
Molecular Formula:C4H6OS
InChIKey:JCAIBTLLMPPCQU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:256.278
Molecular Formula:C10H12N2O4S
InChIKey:BSDUEKVSSJQACF-KHPPLWFESA-N
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Compound Information
Molecular Weight:286.2794
Molecular Formula:C16H14O5
InChIKey:YGMHIBLUWGDWKP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:192.233
Molecular Formula:C7H12O4S
InChIKey:BJJLRBCDMWEPSU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:196.309
Molecular Formula:C11H16OS
InChIKey:BVAOYSXJYNNZLR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:386.418
Molecular Formula:C20H18O6S
InChIKey:BSDOLVZMIFVXLH-UWVAXJGDSA-N
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Compound Information
Molecular Weight:295.118
Molecular Formula:C14H8Cl2O3
InChIKey:MWUSAETYTBNPDG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:216.1278
Molecular Formula:C8H9O5P
InChIKey:YXJAQKPRTPHZQC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:154.229
Molecular Formula:C8H10OS
InChIKey:FHZZRIIWMOYGOA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:318.348
Molecular Formula:C15H14N2O4S
InChIKey:DGKPTYOJOLTVNM-AWEZNQCLSA-N
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Compound Information
Molecular Weight:266.378
Molecular Formula:C10H18O4S2
InChIKey:TXPGHURLHGQYST-UHFFFAOYSA-N
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Compound Information
Molecular Weight:227.237
Molecular Formula:C9H9NO4S
InChIKey:PBBABPWNLXPTGO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:139.1088
Molecular Formula:C6H5NO3
InChIKey:BTJIUGUIPKRLHP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:288.343
Molecular Formula:C10H12N2O4S2
InChIKey:HHKPCCJEEWQURO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:196.309
Molecular Formula:C11H16OS
InChIKey:OYAIFWAPCYGKQP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:218.293
Molecular Formula:C8H10O3S2
InChIKey:SQMWHCILMKZYIP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:158.2811
Molecular Formula:C10H22O
InChIKey:MWKFXSUHUHTGQN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:152.235
Molecular Formula:C4H8O2S2
InChIKey:XGISLVMWAFEKFQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:283.343
Molecular Formula:C13H17NO4S
InChIKey:Not Available
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Compound Information
Molecular Weight:136.17
Molecular Formula:C4H8O3S
InChIKey:NSVLVHKWTAPUSU-QWWZWVQMSA-N
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Compound Information
Molecular Weight:321.315
Molecular Formula:C13H14F3NO3S
InChIKey:QPOOUGOANBUNGP-JTQLQIEISA-N
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Compound Information
Molecular Weight:122.1644
Molecular Formula:C8H10O
InChIKey:Not Available
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Compound Information
Molecular Weight:198.304
Molecular Formula:C6H14O3S2
InChIKey:HXPUNBXKOXJTAF-UHFFFAOYSA-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:120.17
Molecular Formula:C4H8O2S
InChIKey:GAUOLZMDPTWNNX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:160.277
Molecular Formula:C8H16OS
InChIKey:IGJSWGQHITWSON-AATRIKPKSA-N
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Compound Information
Molecular Weight:264.295
Molecular Formula:C10H16O6S
InChIKey:RGSZATULVQVWTM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:193.1992
Molecular Formula:C10H11NO3
InChIKey:NSTPXGARCQOSAU-VIFPVBQESA-N
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Compound Information
Molecular Weight:355.408
Molecular Formula:C19H17NO4S
InChIKey:JIBURFRFFJGLNC-INIZCTEOSA-N
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Compound Information
Molecular Weight:168.256
Molecular Formula:C9H12OS
InChIKey:IEMQHSANHRUTQU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:334.387
Molecular Formula:C8H14O8S3
InChIKey:GHJHECYDPPJPOD-CSMHCCOUSA-N
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Compound Information
Molecular Weight:106.187
Molecular Formula:C4H10OS
InChIKey:CCAFPWNGIUBUSD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:344.595
Molecular Formula:C20H40O2S
InChIKey:NJMXAIKXTRUNMH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:78.133
Molecular Formula:C2H6OS
InChIKey:ZSSFPSNLAUYOFG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:141.9445
Molecular Formula:O5P2
InChIKey:YWEUIGNSBFLMFL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:210.0314
Molecular Formula:C4F6O3
InChIKey:QAEDZJGFFMLHHQ-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:272.362
Molecular Formula:C16H16O2S
InChIKey:MIAYDUKJVLFWCI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:449.4526
Molecular Formula:C25H23NO7
InChIKey:BFBGTMUCHUBFCZ-QFIPXVFZSA-N
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Compound Information
Molecular Weight:134.22
Molecular Formula:C4H6OS2
InChIKey:YEVFOUGMEPCZSM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:341.379
Molecular Formula:C15H19NO6S
InChIKey:FRQFWGDHKGDDKV-LBPRGKRZSA-N
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Compound Information
Molecular Weight:218.399
Molecular Formula:C12H26OS
InChIKey:ZOEBBQMMBGXTTI-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:262.28
Molecular Formula:C10H14O6S
InChIKey:JMQRFKVDMQRRKA-UTLUCORTSA-N
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Compound Information
Molecular Weight:320.402
Molecular Formula:C14H24O6S
InChIKey:VLVJYRRMLOEHDT-UPUXHGCUSA-N
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Compound Information
Molecular Weight:228.374
Molecular Formula:C11H16OS2
InChIKey:BGNWMGVAXCBKIY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:284.4772
Molecular Formula:C18H36O2
InChIKey:QIQXTHQIDYTFRH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:119.1207
Molecular Formula:C7H5NO
InChIKey:Not Available
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Compound Information
Molecular Weight:98.143
Molecular Formula:C6H10O
InChIKey:PQANGXXSEABURG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:97.9952
Molecular Formula:H3O4P
InChIKey:NBIIXXVUZAFLBC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:136.236
Molecular Formula:C4H8OS2
InChIKey:VBDLSQFQIUGPSA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:292.35
Molecular Formula:C6H12O7S3
InChIKey:FSCHWJSRBQWUSX-PHDIDXHHSA-N
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Compound Information
Molecular Weight:152.2334
Molecular Formula:C10H16O
InChIKey:YKYRCPFRUXTGHV-BDAKNGLRSA-N
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Compound Information
Molecular Weight:168.256
Molecular Formula:C9H12OS
InChIKey:SCFQXLALQFBVDI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:208.277
Molecular Formula:C11H12O2S
InChIKey:JEXLFDQEYGHOJG-BQYQJAHWSA-N
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Compound Information
Molecular Weight:295.2894
Molecular Formula:C17H13NO4
InChIKey:VAYRSTHMTWUHGE-AWEZNQCLSA-N
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Compound Information
Molecular Weight:226.2274
Molecular Formula:C14H10O3
InChIKey:CHIHQLCVLOXUJW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:199.227
Molecular Formula:C8H9NO3S
InChIKey:IBGZERXMBRREFH-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:281.2613
Molecular Formula:C13H15NO6
InChIKey:PVFCXMDXBIEMQG-JTQLQIEISA-N
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Compound Information
Molecular Weight:290.494
Molecular Formula:C13H26O3SSi
InChIKey:CEOYQZVLNSNHAJ-CHWSQXEVSA-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:299.3212
Molecular Formula:C17H17NO4
InChIKey:Not Available
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Compound Information
Molecular Weight:156.29
Molecular Formula:C3H8OS3
InChIKey:PVUZSKRNQWELBA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:148.223
Molecular Formula:C6H12O2S
InChIKey:DMNHXVSTWJJMMA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:220.243
Molecular Formula:C8H12O5S
InChIKey:NCPXHWYKOQUYEK-HTQZYQBOSA-N
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Compound Information
Molecular Weight:156.2652
Molecular Formula:C10H20O
InChIKey:CCOQPGVQAWPUPE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:37.467
Molecular Formula:ClH
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:162.293
Molecular Formula:C8H18OS
InChIKey:WBKYWYGVKKUKNR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:227.2585
Molecular Formula:C14H13NO2
InChIKey:OFSBBVCLWMCGNY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:182.283
Molecular Formula:C10H14OS
InChIKey:MTSODOPAKXQRIB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:122.1213
Molecular Formula:C7H6O2
InChIKey:WPYMKLBDIGXBTP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:134.24
Molecular Formula:C6H14OS
InChIKey:NWJSEMAXCSSRTP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:260.2836
Molecular Formula:C12H20O6
InChIKey:KEJGAYKWRDILTF-DEMCRKGTSA-N
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Compound Information
Molecular Weight:152.278
Molecular Formula:C5H12OS2
InChIKey:GOJNQUPPOYYXQA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:162.25
Molecular Formula:C7H14O2S
InChIKey:ZNQULQOUBAOOKI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:260.151
Molecular Formula:C9H10BrNOS
InChIKey:VYXQNQJEXXBWFJ-IZZDOVSWSA-N
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Compound Information
Molecular Weight:316.2225
Molecular Formula:C14H8N2O7
InChIKey:JYMVSZGJZRQOFY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:76.118
Molecular Formula:C2H4OS
InChIKey:PCYCVCFVEKMHGA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:239.057
Molecular Formula:C4H9Cl2O3PS
InChIKey:UJWFQNFEMNXTHE-UHFFFAOYSA-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:148.223
Molecular Formula:C6H12O2S
InChIKey:XNJFDDUZBFTGRP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:154.229
Molecular Formula:C8H10OS
InChIKey:USUGKGZNYHHQAW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:326.455
Molecular Formula:C8H5Cl5OS
InChIKey:OFNFZAQSOSQMHO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:136.191
Molecular Formula:C9H12O
InChIKey:BPRYUXCVCCNUFE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:120.17
Molecular Formula:C4H8O2S
InChIKey:LCUMNXCSNFGGGH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:100.1158
Molecular Formula:C5H8O2
InChIKey:YYPNJNDODFVZLE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:210.271
Molecular Formula:C6H10O4S2
InChIKey:QPUSWLUWUROOIU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:192.233
Molecular Formula:C7H12O4S
InChIKey:NIDRBHZAXVBJRK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:146.1412
Molecular Formula:C6H10O4
InChIKey:WNLRTRBMVRJNCN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:407.5036
Molecular Formula:C28H25NO2
InChIKey:XLDAXFJBEVRMHU-SANMLTNESA-N
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Compound Information
Molecular Weight:80.133
Molecular Formula:C2H6OS
InChIKey:IAZDPXIOMUYVGZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:230.3761
Molecular Formula:C11H22O3Si
InChIKey:MUPHNLAMZYHISA-QWRGUYRKSA-N
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Compound Information
Molecular Weight:290.494
Molecular Formula:C13H26O3SSi
InChIKey:CEOYQZVLNSNHAJ-STQMWFEESA-N
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Compound Information
Molecular Weight:230.3761
Molecular Formula:C11H22O3Si
InChIKey:MUPHNLAMZYHISA-WDEREUQCSA-N
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Compound Information
Molecular Weight:290.494
Molecular Formula:C13H26O3SSi
InChIKey:CEOYQZVLNSNHAJ-QWHCGFSZSA-N
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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:386.418
Molecular Formula:C20H18O6S
InChIKey:BSDOLVZMIFVXLH-FUHIMQAGSA-N
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Compound Information
Molecular Weight:136.17
Molecular Formula:C4H8O3S
InChIKey:NSVLVHKWTAPUSU-OBLUMXEWSA-N
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Compound Information
Molecular Weight:178.206
Molecular Formula:C6H10O4S
InChIKey:YGBAJPRXOODRBG-PBXRRBTRSA-N
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Compound Information
Molecular Weight:220.243
Molecular Formula:C8H12O5S
InChIKey:NCPXHWYKOQUYEK-SZIUVUDRSA-N
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Compound Information
Molecular Weight:262.28
Molecular Formula:C10H14O6S
InChIKey:JMQRFKVDMQRRKA-BBBLOLIVSA-N
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Compound Information
Molecular Weight:292.35
Molecular Formula:C6H12O7S3
InChIKey:FSCHWJSRBQWUSX-GDCRSALOSA-N
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Compound Information
Molecular Weight:334.387
Molecular Formula:C8H14O8S3
InChIKey:GHJHECYDPPJPOD-PRJMDXOYSA-N
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Compound Information
Molecular Weight:344.382
Molecular Formula:C18H16O5S
InChIKey:DRVDDDBOXHYOOW-LZFXEFOOSA-N
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Compound Information
Molecular Weight:386.418
Molecular Formula:C20H18O6S
InChIKey:BSDOLVZMIFVXLH-HLIPFELVSA-N
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Compound Information
Molecular Weight:267.11
Molecular Formula:C6H13Cl2O3PS
InChIKey:YHWGKFPZHCYHIQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:162.207
Molecular Formula:C6H10O3S
InChIKey:QWLQYJWYDDOEEZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:212.265
Molecular Formula:C10H12O3S
InChIKey:HVVJMTVECSPOGD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:224.276
Molecular Formula:C11H12O3S
InChIKey:QJPSKJVJHMBSKP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:176.233
Molecular Formula:C7H12O3S
InChIKey:BIEBUOIPQUUPPX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:195.238
Molecular Formula:C9H9NO2S
InChIKey:BBXNFQKLUYVXQY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:188.287
Molecular Formula:C9H16O2S
InChIKey:QBUQLAOCMYIBEI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:201.286
Molecular Formula:C9H15NO2S
InChIKey:CCKMOBDWRKOMQF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:154.229
Molecular Formula:C8H10OS
InChIKey:LISVNGUOWUKZQY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:162.207
Molecular Formula:C6H10O3S
InChIKey:UDACWWYDFFSTMP-RVOMKPBNSA-N
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Compound Information
Molecular Weight:250.237
Molecular Formula:C10H9F3O2S
InChIKey:XIRUVUFOHJLLGY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:228.269
Molecular Formula:C6H13O3PS2
InChIKey:AUQLRDMWKLCLDV-AATRIKPKSA-N
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Compound Information
Molecular Weight:174.261
Molecular Formula:C8H14O2S
InChIKey:GGFPXDIIWRCYOW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:220.287
Molecular Formula:C12H12O2S
InChIKey:IFGOVOJKJWUHAL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:208.277
Molecular Formula:C11H12O2S
InChIKey:AWBMXUCBYMGFKI-BQYQJAHWSA-N
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Compound Information
Molecular Weight:408.421
Molecular Formula:C16H24O10S
InChIKey:NJSSKOGXHHTXMM-UYCJLYLSSA-N
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Compound Information
Molecular Weight:208.237
Molecular Formula:C9H8N2O2S
InChIKey:PVMHAKZMYQYFII-UHFFFAOYSA-N
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Compound Information
Molecular Weight:242.273
Molecular Formula:C8H19O4PS
InChIKey:WDLAQSGUHGQQJH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:208.277
Molecular Formula:C11H12O2S
InChIKey:BFYLOSNYZNJKCW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:201.286
Molecular Formula:C9H15NO2S
InChIKey:FYFSTZMFCZXROQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:215.336
Molecular Formula:C9H13NOS2
InChIKey:GMEVDWBVLFQGBM-VQHVLOKHSA-N
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Compound Information
Molecular Weight:240.276
Molecular Formula:C11H12O4S
InChIKey:CUAZXMRCCMITAL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:222.303
Molecular Formula:C12H14O2S
InChIKey:AGAHZTAWFFGIDZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:130.1418
Molecular Formula:C6H10O3
InChIKey:WYVAMUWZEOHJOQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:246.777
Molecular Formula:C10H11ClOS2
InChIKey:HVQHBGUZUQQXMR-JXMROGBWSA-N
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Compound Information
Molecular Weight:292.31
Molecular Formula:C13H12N2O4S
InChIKey:RSYZQSQIENQNIB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:262.204
Molecular Formula:C7H9F3O5S
InChIKey:MYVQYKQVRKLPNK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:94.497
Molecular Formula:C2H3ClO2
InChIKey:Not Available
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Compound Information
Molecular Weight:212.265
Molecular Formula:C10H12O3S
InChIKey:IWHKLMYUEDUNQL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:218.359
Molecular Formula:C8H10OS3
InChIKey:RBUVYNDBSUETFA-VURMDHGXSA-N
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