Standard Article

Oxidation of Alcohols to Carbonyl Compounds via Alkoxysulfonium Ylides: The Moffatt, Swern, and Related Oxidations

  1. Thomas T. Tidwell

Published Online: 15 OCT 2004

DOI: 10.1002/0471264180.or039.03

Organic Reactions

Organic Reactions

How to Cite

Tidwell, T. T. 2004. Oxidation of Alcohols to Carbonyl Compounds via Alkoxysulfonium Ylides: The Moffatt, Swern, and Related Oxidations. Organic Reactions. 39:3:297–555.

Author Information

  1. University of Toronto, Department of Chemistry, Scarborough, Ontario, Canada

Publication History

  1. Published Online: 15 OCT 2004

Chemistry Terms

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Abstract

The use of dimethyl sulfoxide as an oxidizing agent began with the discoveries by Kornblum and co-workers that certain α-bromo ketones were converted into glyoxals under mild conditions by treatment with dimethyl sulfoxide, and that primary tosylates such as n-octyl tosylate were converted into the corresponding aldehydes using dimethyl sulfoxide and sodium bicarbonate at 150° for 3 minutes. The initial step of the reactions involves a displacement by dimethyl sulfoxide giving an alkoxysulfonium ion and this species undergoes a 1,2 elimination assisted by base to give the carbonyl product

A few years later it was discovered that alcohols were oxidized at room temperature to carbonyl compounds by dimethyl sulfoxide, dicyclohexylcarbodiimide (DCC), and phosphoric acid. This reaction was immediately recognized as an effective and mild procedure for sensitive substrates, and the extensive studies by this group and the development of alternative variations elsewhere have been the subject of several earlier reviews.

The course of the Moffatt procedure is summarized. The key intermediate in this process is the oxysulfonium ylide, which appears to be common to all of the variations of dimethyl sulfoxide oxidations, and which reacts intramolecularly to give the products.

Other related procedures that were soon developed utilize dimethyl sulfoxide activated by acetic anhydride, phosphorus pentoxide, sulfur trioxide/pyridine complex, and chlorine. Reaction of alcohols with phosgene to give chloroformates which react with dimethyl sulfoxide to give alkoxysulfonium ions, followed by reaction with triethylamine, also effects oxidation.

The reaction of the complexes of dimethyl sulfide and chlorine or N-chlorosuccinimide (NCS) with alcohols is proposed to give the same alkoxysulfonium complexes, which are efficiently converted into carbonyl products upon addition of triethylamine. Electrochemical activation of sulfides has also been successfully utilized.

The activation of dimethyl sulfoxide is effected by many reagents, and these reactions as well as those involving activated sulfides evidently involve the alkoxysulfonium ion and the decisive oxidation step which occurs via the alkoxysulfonium ylide in all the reactions. Activation of dimethyl sulfoxide by oxalyl chloride, has become the most used of these oxidation procedures, but several of the other methods are also convenient and efficient.

Keywords:

  • oxidation;
  • alcohols;
  • carbonyls;
  • oxidants;
  • Moffat oxidation;
  • Swern oxidation;
  • scope;
  • limitations;
  • activators;
  • amine bases;
  • alcohol substrates;
  • side reactions;
  • ketols;
  • polyols;
  • non-alcohol substrates;
  • other oxidations;
  • primary alcohols;
  • carbohydrate alcohols;
  • secondary alcohols;
  • diols;
  • experimental procedures

Featured Compounds

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  1. 1 - 250
Compound Information
Molecular Weight:72.1057
Molecular Formula:C4H8O
InChIKey:AMIMRNSIRUDHCM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:112.1696
Molecular Formula:C7H12O
InChIKey:Not Available
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Compound Information
Molecular Weight:86.1323
Molecular Formula:C5H10O
InChIKey:Not Available
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Compound Information
Molecular Weight:82.1005
Molecular Formula:C5H6O
InChIKey:VWYVHZFRBJJWSM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:128.212
Molecular Formula:C8H16O
InChIKey:NLONCNDGTVCHTN-SFYZADRCSA-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:213.1975
Molecular Formula:C8H14F3NO2
InChIKey:BGCYSPBEPMOQII-UHFFFAOYSA-N
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Compound Information
Molecular Weight:140.567
Molecular Formula:C7H5ClO
InChIKey:FPYUJUBAXZAQNL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:171.1937
Molecular Formula:C8H13NO3
InChIKey:ZSXRKAJYQOYRFW-ZETCQYMHSA-N
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Compound Information
Molecular Weight:107.11
Molecular Formula:C6H5NO
InChIKey:Not Available
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Compound Information
Molecular Weight:130.2603
Molecular Formula:C6H14OSi
InChIKey:DLZRCTHPQQALDW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:153.1354
Molecular Formula:C7H7NO3
InChIKey:BWRBVBFLFQKBPT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:108.066
Molecular Formula:C8H5Li
InChIKey:Not Available
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Compound Information
Molecular Weight:112.1696
Molecular Formula:C7H12O
InChIKey:OGDYROFIIXDTQK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:153.1354
Molecular Formula:C7H7NO3
InChIKey:CWNPOQFCIIFQDM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:130.1418
Molecular Formula:C6H10O3
InChIKey:RLBQTMYBGOKQBU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:132.2761
Molecular Formula:C6H16OSi
InChIKey:YNUUCDHAZGAVEZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:192.178
Molecular Formula:C7H8N6O
InChIKey:CYNARAWTVHQHDI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:126.1962
Molecular Formula:C8H14O
InChIKey:NXKMMWGHYIZNSK-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:112.1696
Molecular Formula:C7H12O
InChIKey:DBDRAMKGMQVTLR-MEKDEQNOSA-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:114.1855
Molecular Formula:C7H14O
InChIKey:Not Available
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Compound Information
Molecular Weight:120.1485
Molecular Formula:C8H8O
InChIKey:DTUQWGWMVIHBKE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:297.345
Molecular Formula:C14H17FNO3S
InChIKey:HXUOPSAHPZTNGS-UHFFFAOYSA-M
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Compound Information
Molecular Weight:124.1803
Molecular Formula:C8H12O
InChIKey:LWFSGMOGTFTZDN-GGWOSOGESA-N
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Compound Information
Molecular Weight:124.964
Molecular Formula:C2H5BrO
InChIKey:LDLCZOVUSADOIV-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:299.03
Molecular Formula:Cl5Sb
InChIKey:VMPVEPPRYRXYNP-UHFFFAOYSA-I
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Compound Information
Molecular Weight:110.1537
Molecular Formula:C7H10O
InChIKey:XWZLMLGAYCVWAU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:128.169
Molecular Formula:C7H12O2
InChIKey:GENLUEWRJJTDQS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:112.1696
Molecular Formula:C7H12O
InChIKey:PSWHODJVUOXHKA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:186.3235
Molecular Formula:C9H18O2Si
InChIKey:SLFQAFMYMFDIOX-BQYQJAHWSA-N
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Compound Information
Molecular Weight:157.233
Molecular Formula:C7H11NOS
InChIKey:MXRILYGHQGAJEB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:146.1843
Molecular Formula:C7H14O3
InChIKey:YYEZYENJAMOWHW-LURJTMIESA-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:100.1589
Molecular Formula:C6H12O
InChIKey:ZCHHRLHTBGRGOT-SNAWJCMRSA-N
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Compound Information
Molecular Weight:146.294
Molecular Formula:C8H18S
InChIKey:HTIRHQRTDBPHNZ-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:151.1195
Molecular Formula:C7H5NO3
InChIKey:ZETIVVHRRQLWFW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:128.169
Molecular Formula:C7H12O2
InChIKey:XAAMQNSLMJCNOO-RQJHMYQMSA-N
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Compound Information
Molecular Weight:88.1482
Molecular Formula:C5H12O
InChIKey:KPSSIOMAKSHJJG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:109.1259
Molecular Formula:C6H7NO
InChIKey:PTMBWNZJOQBTBK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:137.179
Molecular Formula:C8H11NO
InChIKey:ZUGAIMFLQLPTKB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:174.196
Molecular Formula:C2H6O5S2
InChIKey:IZDROVVXIHRYMH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:106.551
Molecular Formula:C4H7ClO
InChIKey:DOQLCJMCQWQQHK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:130.1849
Molecular Formula:C7H14O2
InChIKey:UAWSSJWVDSZYPU-RNFRBKRXSA-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:122.507
Molecular Formula:C3H3ClO3
InChIKey:ZXUQEPZWVQIOJE-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:109.1259
Molecular Formula:C6H7NO
InChIKey:SHNUBALDGXWUJI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:128.169
Molecular Formula:C7H12O2
InChIKey:YWYMVFBMJWNDIX-ZETCQYMHSA-N
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Compound Information
Molecular Weight:109.03
Molecular Formula:C2H6Se
InChIKey:RVIXKDRPFPUUOO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:144.1684
Molecular Formula:C7H12O3
InChIKey:BASUVKNKERZYGZ-LURJTMIESA-N
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Compound Information
Molecular Weight:107.11
Molecular Formula:C6H5NO
InChIKey:Not Available
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Compound Information
Molecular Weight:72.1057
Molecular Formula:C4H8O
InChIKey:ZTQSAGDEMFDKMZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:130.1849
Molecular Formula:C7H14O2
InChIKey:TWUZZZWSLBSFGG-RQJHMYQMSA-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:102.1317
Molecular Formula:C5H10O2
InChIKey:HJXAWVLTVYGIBH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:504.7431
Molecular Formula:C34H48O3
InChIKey:VINIYLWAMAFFEX-BNQRXEIYSA-N
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Compound Information
Molecular Weight:98.916
Molecular Formula:CCl2O
InChIKey:Not Available
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Compound Information
Molecular Weight:173.2096
Molecular Formula:C8H15NO3
InChIKey:VWWDYDCOZHYNJG-ZETCQYMHSA-N
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Compound Information
Molecular Weight:136.1479
Molecular Formula:C8H8O2
InChIKey:ZRSNZINYAWTAHE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:96.0841
Molecular Formula:C5H4O2
InChIKey:AZVSIHIBYRHSLB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:96.1271
Molecular Formula:C6H8O
InChIKey:VVRVSKFQOPUGNO-RITPCOANSA-N
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Compound Information
Molecular Weight:102.1748
Molecular Formula:C6H14O
InChIKey:ZSIAUFGUXNUGDI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:74.1216
Molecular Formula:C4H10O
InChIKey:ZXEKIIBDNHEJCQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:31.9988
Molecular Formula:O2
InChIKey:MHAJPDPJQMAIIY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:98.078
Molecular Formula:H2O4S
InChIKey:QAOWNCQODCNURD-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:84.1164
Molecular Formula:C5H8O
InChIKey:CRWVOXFUXPYTRK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:134.1736
Molecular Formula:C6H14O3
InChIKey:AGDCYCRHQFDLPD-LURJTMIESA-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:110.1537
Molecular Formula:C7H10O
InChIKey:RRDUXTLFKYGTML-MEKDEQNOSA-N
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Compound Information
Molecular Weight:190.1621
Molecular Formula:C7H6N6O
InChIKey:QBSIXCBKOMWSBZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:118.24
Molecular Formula:C6H14S
InChIKey:XYWDPYKBIRQXQS-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:62.043
Molecular Formula:C2H3FO
InChIKey:YYDWYJJLVYDJLV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:211.1816
Molecular Formula:C8H12F3NO2
InChIKey:DWJLGBRTRRHYQC-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:102.0886
Molecular Formula:C4H6O3
InChIKey:Not Available
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Compound Information
Molecular Weight:114.1855
Molecular Formula:C7H14O
InChIKey:VSSAZBXXNIABDN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:179.2004
Molecular Formula:C6H18N3OP
InChIKey:GNOIPBMMFNIUFM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:108.1378
Molecular Formula:C7H8O
InChIKey:WVDDGKGOMKODPV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:62.134
Molecular Formula:C2H6S
InChIKey:QMMFVYPAHWMCMS-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:124.1803
Molecular Formula:C8H12O
InChIKey:NHIXWDCCYHGFMD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:98.143
Molecular Formula:C6H10O
InChIKey:Not Available
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Compound Information
Molecular Weight:96.1271
Molecular Formula:C6H8O
InChIKey:BATOPAZDIZEVQF-MQQKCMAXSA-N
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Compound Information
Molecular Weight:64.0589
Molecular Formula:C2H5FO
InChIKey:GGDYAKVUZMZKRV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:156.2975
Molecular Formula:C8H16OSi
InChIKey:ZWGKEUBNJYCXGM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:114.1855
Molecular Formula:C7H14O
InChIKey:IHZLWFWSVIGUST-ZCFIWIBFSA-N
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Compound Information
Molecular Weight:154.2817
Molecular Formula:C8H14OSi
InChIKey:NBCKPIFPOYTSFE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:136.1479
Molecular Formula:C8H8O2
InChIKey:XFFILAFLGDUMBF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:98.143
Molecular Formula:C6H10O
InChIKey:MEIRRNXMZYDVDW-MQQKCMAXSA-N
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Compound Information
Molecular Weight:98.143
Molecular Formula:C6H10O
InChIKey:HXVBFRLIDBYJMF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:124.1803
Molecular Formula:C8H12O
InChIKey:DUUGWLGPIZCNLM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:204.3403
Molecular Formula:C12H16OSi
InChIKey:AGPNRAWVEQKMQA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:258.3123
Molecular Formula:C16H18O3
InChIKey:Not Available
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Compound Information
Molecular Weight:126.1962
Molecular Formula:C8H14O
InChIKey:YRNFKLLSHCOTBF-GGWOSOGESA-N
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Compound Information
Molecular Weight:126.1531
Molecular Formula:C7H10O2
InChIKey:LIEHUKGXYCBIKA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:283.319
Molecular Formula:C13H15FNO3S
InChIKey:HQWDKLAIDBOLFE-UHFFFAOYSA-M
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Compound Information
Molecular Weight:141.534
Molecular Formula:CClNO3S
InChIKey:WRJWRGBVPUUDLA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:114.1855
Molecular Formula:C7H14O
InChIKey:ZSJUABCTGCNBPF-SSDOTTSWSA-N
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Compound Information
Molecular Weight:144.2868
Molecular Formula:C7H16OSi
InChIKey:BWNLJXBYSUHUET-UHFFFAOYSA-N
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Compound Information
Molecular Weight:104.223
Molecular Formula:C4H12OSi
InChIKey:ZQKNBDOVPOZPLY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:126.1995
Molecular Formula:C7H14N2
InChIKey:BDNKZNFMNDZQMI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:78.498
Molecular Formula:C2H3ClO
InChIKey:WETWJCDKMRHUPV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:153.1354
Molecular Formula:C7H7NO3
InChIKey:Not Available
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Compound Information
Molecular Weight:130.1849
Molecular Formula:C7H14O2
InChIKey:WZLAWJLXUDNHSD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:157.2102
Molecular Formula:C8H15NO2
InChIKey:KBPLQOJEEXMFMY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:138.1638
Molecular Formula:C8H10O2
InChIKey:MSHFRERJPWKJFX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:132.1577
Molecular Formula:C6H12O3
InChIKey:MPEMSDRABAGGLU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:151.1195
Molecular Formula:C7H5NO3
InChIKey:BXRFQSNOROATLV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:80.063
Molecular Formula:O3S
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:126.1962
Molecular Formula:C8H14O
InChIKey:BCBRYLGSFZGALI-SFYZADRCSA-N
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Compound Information
Molecular Weight:108.567
Molecular Formula:C4H9ClO
InChIKey:Not Available
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Compound Information
Molecular Weight:129.2432
Molecular Formula:C8H19N
InChIKey:JGFZNNIVVJXRND-UHFFFAOYSA-N
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Compound Information
Molecular Weight:112.15
Molecular Formula:C5H4OS
InChIKey:Not Available
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Compound Information
Molecular Weight:502.7272
Molecular Formula:C34H46O3
InChIKey:CIXHKILLRPWAPJ-RDLNWRCOSA-N
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Compound Information
Molecular Weight:283.2407
Molecular Formula:C10H13N5O5
InChIKey:CFOQUIOWNVKBIC-FJFJXFQQSA-N
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Compound Information
Molecular Weight:142.583
Molecular Formula:C7H7ClO
InChIKey:PTHGDVCPCZKZKR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:144.2114
Molecular Formula:C8H16O2
InChIKey:PFEZFCUFFWFUKS-HTQZYQBOSA-N
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Compound Information
Molecular Weight:81.0727
Molecular Formula:C4H3NO
InChIKey:KSMNKZULGQZFCH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:100.1589
Molecular Formula:C6H12O
InChIKey:JARKCYVAAOWBJS-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:83.0886
Molecular Formula:C4H5NO
InChIKey:LZJDCFUZEZQGQR-OWOJBTEDSA-N
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Compound Information
Molecular Weight:98.143
Molecular Formula:C6H10O
InChIKey:BBEUBSMPIQDNHL-RITPCOANSA-N
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Compound Information
Molecular Weight:126.1962
Molecular Formula:C8H14O
InChIKey:FMBSEAXLUWAECJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:128.169
Molecular Formula:C7H12O2
InChIKey:MGPOZFJWYRNWBH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:109.1259
Molecular Formula:C6H7NO
InChIKey:MVQVNTPHUGQQHK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:142.271
Molecular Formula:C7H14OSi
InChIKey:IJZVXORTZQWNLO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:525.746
Molecular Formula:C22H39N5O6Si2
InChIKey:AVNRGPRFBYSGHF-QTQZEZTPSA-N
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Compound Information
Molecular Weight:142.1956
Molecular Formula:C8H14O2
InChIKey:YWFUECKBUFORTA-HTQZYQBOSA-N
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Compound Information
Molecular Weight:114.166
Molecular Formula:C5H6OS
InChIKey:ZPHGMBGIFODUMF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:96.1271
Molecular Formula:C6H8O
InChIKey:JJSQZROPSFMJFW-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:140.567
Molecular Formula:C7H5ClO
InChIKey:AVPYQKSLYISFPO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:126.1531
Molecular Formula:C7H10O2
InChIKey:ZBBHXNGZHKUXSV-RNFRBKRXSA-N
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Compound Information
Molecular Weight:116.2013
Molecular Formula:C7H16O
InChIKey:YGZVAQICDGBHMD-SSDOTTSWSA-N
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Compound Information
Molecular Weight:151.1195
Molecular Formula:C7H5NO3
InChIKey:CMWKITSNTDAEDT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:126.1962
Molecular Formula:C8H14O
InChIKey:YGBJEJWGTXEPQB-IAROGAJJSA-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:124.1372
Molecular Formula:C7H8O2
InChIKey:GWRQHQCUFUBCKJ-RNFRBKRXSA-N
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Compound Information
Molecular Weight:124.1803
Molecular Formula:C8H12O
InChIKey:FUIDWNGSIAABEJ-IAROGAJJSA-N
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Compound Information
Molecular Weight:100.1158
Molecular Formula:C5H8O2
InChIKey:GLZFKAYNZITDIA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:110.1537
Molecular Formula:C7H10O
InChIKey:XWZLMLGAYCVWAU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:135.1632
Molecular Formula:C8H9NO
InChIKey:MQGVOSGGRHAKOE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:126.1962
Molecular Formula:C8H14O
InChIKey:TTWYFVOMGMBZCF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:98.0999
Molecular Formula:C5H6O2
InChIKey:STJIISDMSMJQQK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:130.1849
Molecular Formula:C7H14O2
InChIKey:OIMFRUOWDFCALV-ZETCQYMHSA-N
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Compound Information
Molecular Weight:362.4013
Molecular Formula:C23H23O2P
InChIKey:KZENFXVDPUMQOE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:124.1803
Molecular Formula:C8H12O
InChIKey:CZEGJNUXOXZUDR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:116.2013
Molecular Formula:C7H16O
InChIKey:IWWVOLGZHKFWKK-ZCFIWIBFSA-N
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Compound Information
Molecular Weight:142.583
Molecular Formula:C7H7ClO
InChIKey:MBYQPPXEXWRMQC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:107.11
Molecular Formula:C6H5NO
InChIKey:CSDSSGBPEUDDEE-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:132.1577
Molecular Formula:C6H12O3
InChIKey:QMLOPHHMLMSUAU-LURJTMIESA-N
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Compound Information
Molecular Weight:155.1943
Molecular Formula:C8H13NO2
InChIKey:VNVCCHXGWLFUHW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:128.169
Molecular Formula:C7H12O2
InChIKey:YYPIRPUJHAFFAO-RNFRBKRXSA-N
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Compound Information
Molecular Weight:122.949
Molecular Formula:C2H3BrO
InChIKey:NMPVEAUIHMEAQP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:318.68
Molecular Formula:C4H6HgO4
InChIKey:BRMYZIKAHFEUFJ-UHFFFAOYSA-L
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Compound Information
Molecular Weight:155.217
Molecular Formula:C7H9NOS
InChIKey:ZHDUCEKSKRLFFR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:210.982
Molecular Formula:C6H5Cl2O2P
InChIKey:Not Available
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Compound Information
Molecular Weight:126.926
Molecular Formula:C2Cl2O2
InChIKey:CTSLXHKWHWQRSH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:138.1638
Molecular Formula:C8H10O2
InChIKey:QCDWFXQBSFUVSP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:152.2334
Molecular Formula:C10H16O
InChIKey:Not Available
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Compound Information
Molecular Weight:180.3189
Molecular Formula:C10H16OSi
InChIKey:PTPNVXDZVXYKNE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:198.2588
Molecular Formula:C11H18O3
InChIKey:ZUNKHQNFVYBJJJ-HZTONROUSA-N
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Compound Information
Molecular Weight:186.2481
Molecular Formula:C10H18O3
InChIKey:WZOKEHJNDMTROH-KRBWIIOGSA-N
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Compound Information
Molecular Weight:182.2669
Molecular Formula:C9H11FOSi
InChIKey:HWHFYSIMANENSF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:192.2031
Molecular Formula:C9H14F2O2
InChIKey:TVGBPWAXTUUZIA-SFYZADRCSA-N
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Compound Information
Molecular Weight:176.2548
Molecular Formula:C12H16O
InChIKey:XPYKOJLMORBJQP-NSHDSACASA-N
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Compound Information
Molecular Weight:202.2906
Molecular Formula:C11H22O3
InChIKey:AUVYISJKWXXSCT-VHSXEESVSA-N
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Compound Information
Molecular Weight:156.1791
Molecular Formula:C8H12O3
InChIKey:APLLAACNTMNDSE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:201.3058
Molecular Formula:C11H23NO2
InChIKey:FZGORZGEKIXNPS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:198.2588
Molecular Formula:C11H18O3
InChIKey:IRWYTLXEZJKYIR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:202.2906
Molecular Formula:C11H22O3
InChIKey:NHCIXEPZNPKEAR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:284.093
Molecular Formula:C11H9IO
InChIKey:LEZXJGCBDJGUPN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:242.401
Molecular Formula:C12H18OS2
InChIKey:OVAIPKDZCBCPSE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:244.417
Molecular Formula:C12H20OS2
InChIKey:WHXMOHPGIAMONJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:423.569
Molecular Formula:C21H34N3O4S
InChIKey:GBCAVSYHPPARHX-UHFFFAOYSA-M
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Compound Information
Molecular Weight:140.2227
Molecular Formula:C9H16O
InChIKey:GHEWOVQEZDDGPR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:217.3052
Molecular Formula:C11H23NO3
InChIKey:LQTMEOSBXTVYRM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:207.2689
Molecular Formula:C12H17NO2
InChIKey:QTMGPNFCVVYLHR-HOSYDEDBSA-N
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Compound Information
Molecular Weight:178.2707
Molecular Formula:C12H18O
InChIKey:BLQURGBJSSSGAU-BKUVIOGVSA-N
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Compound Information
Molecular Weight:230.3761
Molecular Formula:C11H22O3Si
InChIKey:RKOCBRZUOIWVQU-UWVGGRQHSA-N
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Compound Information
Molecular Weight:136.191
Molecular Formula:C9H12O
InChIKey:XTJONMNIEHIOOX-AYMMMOKOSA-N
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Compound Information
Molecular Weight:196.2429
Molecular Formula:C11H16O3
InChIKey:RNDKORNZLPJJLH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:154.2493
Molecular Formula:C10H18O
InChIKey:LDWAIHWGMRVEFR-CFCGPWAMSA-N
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Compound Information
Molecular Weight:230.2576
Molecular Formula:C11H18O5
InChIKey:WQQSWEXRXFUPJG-DTWKUNHWSA-N
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Compound Information
Molecular Weight:150.1745
Molecular Formula:C9H10O2
InChIKey:NFNOAHXEQXMCGT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:200.2747
Molecular Formula:C11H20O3
InChIKey:PRGUNFCZRODZGQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:208.3721
Molecular Formula:C12H20OSi
InChIKey:MMCIZENKIQGCEY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:138.2069
Molecular Formula:C9H14O
InChIKey:CZYVCAJKUNEWLC-HRDYMLBCSA-N
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Compound Information
Molecular Weight:224.21
Molecular Formula:C11H12O5
InChIKey:NIPCRRFDAHDJAU-SNZBGZMYSA-N
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Compound Information
Molecular Weight:184.2322
Molecular Formula:C10H16O3
InChIKey:NOQXZVKCFUOBCC-KRBWIIOGSA-N
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Compound Information
Molecular Weight:172.2215
Molecular Formula:C9H16O3
InChIKey:ZIJFFXCELDVXGD-ZETCQYMHSA-N
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Compound Information
Molecular Weight:195.2582
Molecular Formula:C11H17NO2
InChIKey:JPEHJIJAAYFOKF-VHSXEESVSA-N
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Compound Information
Molecular Weight:182.2594
Molecular Formula:C11H18O2
InChIKey:BDVSFVZMCZREJV-ONGXEEELSA-N
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Compound Information
Molecular Weight:152.1904
Molecular Formula:C9H12O2
InChIKey:CUZKCNWZBXLAJX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:192.2542
Molecular Formula:C12H16O2
InChIKey:VQQHSISYNCIVGD-WDEREUQCSA-N
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Compound Information
Molecular Weight:136.191
Molecular Formula:C9H12O
InChIKey:RNDNSYIPLPAXAZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:252.2234
Molecular Formula:C11H12N2O5
InChIKey:KNZGEULBKPEOMZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:180.2435
Molecular Formula:C11H16O2
InChIKey:SKCXVVPAQZXSBM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:172.3077
Molecular Formula:C11H24O
InChIKey:Not Available
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Compound Information
Molecular Weight:203.2786
Molecular Formula:C10H21NO3
InChIKey:OOQRRYDVICNJGC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:180.2866
Molecular Formula:C12H20O
InChIKey:ZBIDZPHRNBZTLT-BKUVIOGVSA-N
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Compound Information
Molecular Weight:172.2215
Molecular Formula:C9H16O3
InChIKey:QBLWUOXMRZHBGS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:333.192
Molecular Formula:C11H23Cl2N2O3P
InChIKey:NGEYWPDTKLTCRN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:242.1483
Molecular Formula:C10H6CrO4
InChIKey:XHHASBGJGDBKRX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:235.344
Molecular Formula:C10H21NO3S
InChIKey:IPIBDQMAIDPJBU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:180.2435
Molecular Formula:C11H16O2
InChIKey:NGRZOWQXYGMVQS-JTQLQIEISA-N
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Compound Information
Molecular Weight:198.2588
Molecular Formula:C11H18O3
InChIKey:LAHVPIKTYRFEDX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:281.3028
Molecular Formula:C11H23NO7
InChIKey:KLENBKMTFRHHRY-UWVGGRQHSA-N
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Compound Information
Molecular Weight:188.2209
Molecular Formula:C9H16O4
InChIKey:MURDZYWJAAACCE-JGVFFNPUSA-N
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Compound Information
Molecular Weight:232.34
Molecular Formula:C11H20O3S
InChIKey:RTQOBXUAPBLPTL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:210.2695
Molecular Formula:C12H18O3
InChIKey:JPPDBNADLKIUOM-BJMVGYQFSA-N
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Compound Information
Molecular Weight:151.2056
Molecular Formula:C9H13NO
InChIKey:VIIZJXNVVJKISZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:164.2011
Molecular Formula:C10H12O2
InChIKey:ZOXCMZXXNOSBHU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:160.2108
Molecular Formula:C8H16O3
InChIKey:BGCAYLDVVXYLOZ-MRVPVSSYSA-N
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Compound Information
Molecular Weight:211.2576
Molecular Formula:C11H17NO3
InChIKey:CVBCDVVGJLJYRO-GARJFASQSA-N
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Compound Information
Molecular Weight:232.2735
Molecular Formula:C11H20O5
InChIKey:HLVMKHVPRFGNHY-DTWKUNHWSA-N
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Compound Information
Molecular Weight:128.212
Molecular Formula:C8H16O
InChIKey:NUJGJRNETVAIRJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:198.2588
Molecular Formula:C11H18O3
InChIKey:VCOBNZIQUBQAGZ-XQRVVYSFSA-N
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Compound Information
Molecular Weight:136.191
Molecular Formula:C9H12O
InChIKey:UYWHLJLZZZHTDQ-NSCUHMNNSA-N
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Compound Information
Molecular Weight:182.3025
Molecular Formula:C12H22O
InChIKey:QGUDMPDYXLMJNK-ARJAWSKDSA-N
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Compound Information
Molecular Weight:170.2487
Molecular Formula:C10H18O2
InChIKey:MTCNKAYPKJJGNQ-UXBLZVDNSA-N
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Compound Information
Molecular Weight:170.2918
Molecular Formula:C11H22O
InChIKey:VXUUJYSSICSSIX-NSHDSACASA-N
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Compound Information
Molecular Weight:232.392
Molecular Formula:C11H24O3Si
InChIKey:LTPKMYSWIFPQBV-UWVGGRQHSA-N
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Compound Information
Molecular Weight:235.302
Molecular Formula:C12H13NO2S
InChIKey:RPDQQKZUOMATMP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:174.2374
Molecular Formula:C9H18O3
InChIKey:ZWFCLXDYXYMEFX-VIFPVBQESA-N
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Compound Information
Molecular Weight:138.2069
Molecular Formula:C9H14O
InChIKey:ZWXKJEZWEXSXKW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:164.2011
Molecular Formula:C10H12O2
InChIKey:Not Available
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Compound Information
Molecular Weight:216.2741
Molecular Formula:C11H20O4
InChIKey:GLQIMIZDXAREEF-MXWKQRLJSA-N
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Compound Information
Molecular Weight:138.2069
Molecular Formula:C9H14O
InChIKey:LGOVJWMIZULEPH-NSCUHMNNSA-N
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Compound Information
Molecular Weight:142.2386
Molecular Formula:C9H18O
InChIKey:AAKBYYSSEPSTTE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:196.286
Molecular Formula:C12H20O2
InChIKey:XVQWCVMVPHXGTK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:168.2759
Molecular Formula:C11H20O
InChIKey:PANBRUWVURLWGY-KTKRTIGZSA-N
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Compound Information
Molecular Weight:178.2707
Molecular Formula:C12H18O
InChIKey:GPYDXUZTYMFYAZ-DVVUODLYSA-N
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Compound Information
Molecular Weight:200.2747
Molecular Formula:C11H20O3
InChIKey:WIZZPXLYPKTTAG-MTULOOOASA-N
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Compound Information
Molecular Weight:173.2096
Molecular Formula:C8H15NO3
InChIKey:OEQRZPWMXXJEKU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:134.1751
Molecular Formula:C9H10O
InChIKey:OOCCDEMITAIZTP-QPJJXVBHSA-N
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Compound Information
Molecular Weight:170.2918
Molecular Formula:C11H22O
InChIKey:KMPQYAYAQWNLME-UHFFFAOYSA-N
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Compound Information
Molecular Weight:175.2255
Molecular Formula:C8H17NO3
InChIKey:PDAFIZPRSXHMCO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:236.202
Molecular Formula:C9H17O5P
InChIKey:OLVOAVLIEKGADJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:210.2695
Molecular Formula:C12H18O3
InChIKey:YODDEHYDMMDDCV-NXAIOARDSA-N
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Compound Information
Molecular Weight:152.2334
Molecular Formula:C10H16O
InChIKey:NQLKPDBZZUIQGM-RKDXNWHRSA-N
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Compound Information
Molecular Weight:186.2481
Molecular Formula:C10H18O3
InChIKey:COLUEOOWVQELHN-SOFGYWHQSA-N
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