Standard Article

Olefin Synthesis by Deoxygenation of Vicinal Diols

  1. Eric Block

Published Online: 15 JUL 2005

DOI: 10.1002/0471264180.or030.02

Organic Reactions

Organic Reactions

How to Cite

Block, E. 2005. Olefin Synthesis by Deoxygenation of Vicinal Diols. Organic Reactions. 30:2:457–566.

Author Information

  1. State University of New York at Albany, Albany, New York

Publication History

  1. Published Online: 15 JUL 2005

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Abstract

Since the discovery in 1963 that 1,3-dioxolane-2-thiones (cyclic thionocarbonates) undergo stereospecific fragmentation to olefins on heating with trivalent phosphorus compounds (the Corey–Winter reaction), a variety of approaches have been developed for the regio- and stereospecific (or stereo-selective) deoxygenation of vicinal diols based on syn elimination from cyclic derivatives. These methods have been particularly useful in synthesizing substrates with delicate structural features such as strained and twisted olefins, unsaturated carbohydrates, macrocyclic lactones, lipids, and polyenes, as well as in establishing the stereochemistry of diol functions in natural products.

This chapter deals primarily with deoxygenation of vicinal diols via cyclic species with X = C, P, Ti, W, or S (suitably functionalized). Brief coverage is given to deoxygenation processes that do not involve cyclic intermediates, whereas routes proceeding via oxiranes or vic-dihalides as separately isolated intermediates are excluded from consideration. The stereochemical equilibration of vicinal diols and the conversion of vicinal hydroxy thiols and dithiols to olefins are also covered in this chapter. Brief reviews have appeared in the literature of the Corey–Winter reaction and of the general topic of deoxygenation of vicinal diols.

Keywords:

  • olefin synthesis;
  • deoxygenation;
  • desulfurization;
  • thionocarbonates;
  • 1,3-dioxolanes;
  • reduction-elimination;
  • vicinal diols;
  • cyclic phosphates;
  • cyclic phosphoramidates;
  • transition metals;
  • cyclic sulfoxylates;
  • stereochemical equilibration;
  • scope;
  • mechanism;
  • experimental procedures

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Compound Information
Molecular Weight:0
Molecular Formula:Not Available
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:128.1705
Molecular Formula:C10H8
InChIKey:UFWIBTONFRDIAS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:224.9
Molecular Formula:HgMg
InChIKey:LHPHQPXEEUZMSG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:84.1595
Molecular Formula:C6H12
InChIKey:BEQGRRJLJLVQAQ-XQRVVYSFSA-N
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Compound Information
Molecular Weight:86.1323
Molecular Formula:C5H10O
InChIKey:Not Available
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Compound Information
Molecular Weight:72.1057
Molecular Formula:C4H8O
InChIKey:ZSPTYLOMNJNZNG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:146.2273
Molecular Formula:C8H18O2
InChIKey:XMTUJCWABCYSIV-SFYZADRCSA-N
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Compound Information
Molecular Weight:110.1968
Molecular Formula:C8H14
InChIKey:URYYVOIYTNXXBN-UPHRSURJSA-N
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Compound Information
Molecular Weight:96.1702
Molecular Formula:C7H12
InChIKey:MVUIDYODAQLMEF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:90.0349
Molecular Formula:C2H2O4
InChIKey:MUBZPKHOEPUJKR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:106.1219
Molecular Formula:C7H6O
InChIKey:BYUGRALWTPEHMX-XBQGMCBBSA-N
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Compound Information
Molecular Weight:116.1583
Molecular Formula:C6H12O2
InChIKey:ZKDRILDNFHGHFS-DUAGOPDLSA-N
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Compound Information
Molecular Weight:110.1968
Molecular Formula:C8H14
InChIKey:FZBNRBFHQXNXHG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:166.1553
Molecular Formula:C6H15O3P
InChIKey:BDZBKCUKTQZUTL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:162.1406
Molecular Formula:C6H10O5
InChIKey:HXZYFFHCVDPSHW-UOWFLXDJSA-N
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Compound Information
Molecular Weight:102.1317
Molecular Formula:C5H10O2
InChIKey:MQPRWPYARBPQJW-ROTTUQNMSA-N
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Compound Information
Molecular Weight:128.235
Molecular Formula:C7H12S
InChIKey:OQIKWIYGPAKNOZ-OWOJBTEDSA-N
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Compound Information
Molecular Weight:178.214
Molecular Formula:C7H6N4S
InChIKey:RAFNCPHFRHZCPS-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:106.1204
Molecular Formula:C4H10O3
InChIKey:ARXKVVRQIIOZGF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:68.117
Molecular Formula:C5H8
InChIKey:NFTHULPHIBKNNM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:72.1488
Molecular Formula:C5H12
InChIKey:OFBQJSOFQDEBGM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:112.2126
Molecular Formula:C8H16
InChIKey:ILPBINAXDRFYPL-HWKANZROSA-N
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Compound Information
Molecular Weight:116.1583
Molecular Formula:C6H12O2
InChIKey:PFURGBBHAOXLIO-OLQVQODUSA-N
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Compound Information
Molecular Weight:94.1112
Molecular Formula:C6H6O
InChIKey:YKCNBNDWSATCJL-OLQVQODUSA-N
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Compound Information
Molecular Weight:122.1198
Molecular Formula:C4H10O4
InChIKey:UNXHWFMMPAWVPI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:250.3147
Molecular Formula:C12H27O3P
InChIKey:XTTGYFREQJCEML-UHFFFAOYSA-N
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Compound Information
Molecular Weight:42.0797
Molecular Formula:C3H6
InChIKey:QQONPFPTGQHPMA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:76.0944
Molecular Formula:C3H8O2
InChIKey:Not Available
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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:178.2292
Molecular Formula:C14H10
InChIKey:MWPLVEDNUUSJAV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:195.896
Molecular Formula:C5FeO5
InChIKey:FYOFOKCECDGJBF-UHFFFAOYSA-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:102.1317
Molecular Formula:C5H10O2
InChIKey:VCVOSERVUCJNPR-SYDPRGILSA-N
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Compound Information
Molecular Weight:110.539
Molecular Formula:C3H7ClO2
InChIKey:SSZWWUDQMAHNAQ-UHFFFAOYSA-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:194.1825
Molecular Formula:C7H14O6
InChIKey:HOVAGTYPODGVJG-VEIUFWFVSA-N
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Compound Information
Molecular Weight:110.1968
Molecular Formula:C8H14
InChIKey:WAXBWZULOIZPKQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:134.1736
Molecular Formula:C6H14O3
InChIKey:XXJWXESWEXIICW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:73.0938
Molecular Formula:C3H7NO
InChIKey:ZMXDDKWLCZADIW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:140.567
Molecular Formula:C7H5ClO
InChIKey:PASDCCFISLVPSO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:96.1702
Molecular Formula:C7H12
InChIKey:CTMHWPIWNRWQEG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:206.1932
Molecular Formula:C8H14O6
InChIKey:YSAVZVORKRDODB-WDSKDSINSA-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:100.1158
Molecular Formula:C5H8O2
InChIKey:IHVWAXHWELFEAT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:70.0898
Molecular Formula:C4H6O
InChIKey:Not Available
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Compound Information
Molecular Weight:142.1956
Molecular Formula:C8H14O2
InChIKey:XHYBKMGLASBLOT-PPSBICQBSA-N
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Compound Information
Molecular Weight:116.1583
Molecular Formula:C6H12O2
InChIKey:WEKSLMZQHJLBGL-WHFBIAKZSA-N
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Compound Information
Molecular Weight:334.0597
Molecular Formula:C6H2F12O2
InChIKey:GKDCWKGUOZVDFX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:114.1424
Molecular Formula:C6H10O2
InChIKey:JCHWRFLELZDWBJ-WHFBIAKZSA-N
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Compound Information
Molecular Weight:134.1305
Molecular Formula:C5H10O4
InChIKey:KZVAAIRBJJYZOW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:54.0904
Molecular Formula:C4H6
InChIKey:CFBGXYDUODCMNS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:72.1057
Molecular Formula:C4H8O
InChIKey:ZEXFAVZTIZXHFA-ONEGZZNKSA-N
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Compound Information
Molecular Weight:76.141
Molecular Formula:CS2
InChIKey:QGJOPFRUJISHPQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:118.1742
Molecular Formula:C6H14O2
InChIKey:IVDFJHOHABJVEH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:37.954
Molecular Formula:AlH4Li
InChIKey:OCZDCIYGECBNKL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:134.1305
Molecular Formula:C5H10O4
InChIKey:QXAMTEJJAZOINB-IMJSIDKUSA-N
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Compound Information
Molecular Weight:172.2646
Molecular Formula:C10H20O2
InChIKey:YQUNEXSJGIVACX-DJLDLDEBSA-N
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Compound Information
Molecular Weight:124.0755
Molecular Formula:C3H9O3P
InChIKey:Not Available
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Compound Information
Molecular Weight:190.647
Molecular Formula:C7H7ClO2S
InChIKey:YYROPELSRYBVMQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:130.1849
Molecular Formula:C7H14O2
InChIKey:IOZFUGDROBQPNP-RQJHMYQMSA-N
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Compound Information
Molecular Weight:136.315
Molecular Formula:Cl2Zn
InChIKey:Not Available
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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:84.045
Molecular Formula:C6H5Li
InChIKey:DBYQHFPBWKKZAT-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:39.9971
Molecular Formula:HNaO
InChIKey:HEMHJVSKTPXQMS-UHFFFAOYSA-M
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Compound Information
Molecular Weight:114.0993
Molecular Formula:C5H6O3
InChIKey:AWNLUIGMHSSXHB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:138.2499
Molecular Formula:C10H18
InChIKey:PJTMQLHFQYFBBB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:146.2273
Molecular Formula:C8H18O2
InChIKey:RJOVKNVJGPMWDT-OCAPTIKFSA-N
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Compound Information
Molecular Weight:98.1861
Molecular Formula:C7H14
InChIKey:OTTZHAVKAVGASB-HYXAFXHYSA-N
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Compound Information
Molecular Weight:418.6337
Molecular Formula:C24H51O3P
InChIKey:FSHIYDNYAOJCPR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:82.1436
Molecular Formula:C6H10
InChIKey:HGCIXCUEYOPUTN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:130.1418
Molecular Formula:C6H10O3
InChIKey:JXLJXLLGFKRPQR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:90.121
Molecular Formula:C4H10O2
InChIKey:Not Available
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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:128.1259
Molecular Formula:C6H8O3
InChIKey:YATRXMNGSLWFHT-LAXKNYFCSA-N
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Compound Information
Molecular Weight:227.773
Molecular Formula:C13H22ClN
InChIKey:HTZCNXWZYVXIMZ-UHFFFAOYSA-M
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Compound Information
Molecular Weight:128.1259
Molecular Formula:C6H8O3
InChIKey:XSJCOWCIXXWUMM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:96.1702
Molecular Formula:C7H12
InChIKey:Not Available
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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:176.2102
Molecular Formula:C8H16O4
InChIKey:YLMFFJPPIFKCBQ-CWKFCGSDSA-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:76.525
Molecular Formula:C3H5Cl
InChIKey:OSDWBNJEKMUWAV-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:164.1565
Molecular Formula:C6H12O5
InChIKey:ZBDGHWFPLXXWRD-AZGQCCRYSA-N
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Compound Information
Molecular Weight:22.98976928
Molecular Formula:Na
InChIKey:MPMYQQHEHYDOCL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:82.1436
Molecular Formula:C6H10
InChIKey:LDPRWJVPCXEVEY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:142.1956
Molecular Formula:C8H14O2
InChIKey:QQDIHWFCXJBTHP-XEDAXZNXSA-N
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Compound Information
Molecular Weight:106.1204
Molecular Formula:C4H10O3
InChIKey:Not Available
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Compound Information
Molecular Weight:114.551
Molecular Formula:CH3ClO2S
InChIKey:QARBMVPHQWIHKH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:186.231
Molecular Formula:C7H10N2O2S
InChIKey:ICGLPKIVTVWCFT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:108.1809
Molecular Formula:C8H12
InChIKey:NSATUTLGIUBWCR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:118.1742
Molecular Formula:C6H14O2
InChIKey:RLWWHEFTJSHFRN-RITPCOANSA-N
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Compound Information
Molecular Weight:169.9922
Molecular Formula:C3H7I
InChIKey:FMKOJHQHASLBPH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:94.1543
Molecular Formula:C7H10
InChIKey:JFNLZVQOOSMTJK-KNVOCYPGSA-N
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Compound Information
Molecular Weight:142.1525
Molecular Formula:C7H10O3
InChIKey:GXVKKBQCNCBKKD-CQMSUOBXSA-N
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Compound Information
Molecular Weight:176.1672
Molecular Formula:C7H12O5
InChIKey:ZSGFRYHJVWRKEA-CKYZJGBBSA-N
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Compound Information
Molecular Weight:92.1384
Molecular Formula:C7H8
InChIKey:YXFVVABEGXRONW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:88.1051
Molecular Formula:C4H8O2
InChIKey:MHPMXFUDCYMCOE-ZXZARUISSA-N
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Compound Information
Molecular Weight:310.2837
Molecular Formula:C18H15O3P
InChIKey:HVLLSGMXQDNUAL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:62.0678
Molecular Formula:C2H6O2
InChIKey:Not Available
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Compound Information
Molecular Weight:166.0219
Molecular Formula:C3F6O
InChIKey:VBZWSGALLODQNC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:248.2744
Molecular Formula:C14H16O4
InChIKey:CULHEDOHPOHBOT-RFQIPJPRSA-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:148.2001
Molecular Formula:C7H16O3
InChIKey:GKASDNZWUGIAMG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:142.1956
Molecular Formula:C8H14O2
InChIKey:QDNGXASCFKSQNV-SFYZADRCSA-N
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Compound Information
Molecular Weight:80.1277
Molecular Formula:C6H8
InChIKey:JYHKXHJIGKWRAV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:58.0791
Molecular Formula:C3H6O
InChIKey:XXROGKLTLUQVRX-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:142.1956
Molecular Formula:C8H14O2
InChIKey:IWRNMIOUWHDUKR-OCAPTIKFSA-N
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Compound Information
Molecular Weight:108.1809
Molecular Formula:C8H12
InChIKey:IBJMNXAEDQNPFI-OCAPTIKFSA-N
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Compound Information
Molecular Weight:141.939
Molecular Formula:CH3I
InChIKey:INQOMBQAUSQDDS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:300.045
Molecular Formula:C6F12
InChIKey:CUKJWRYRLCTJNJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:130.1849
Molecular Formula:C7H14O2
InChIKey:DCYPPXGEIQTVPI-RNFRBKRXSA-N
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Compound Information
Molecular Weight:154.226
Molecular Formula:Cl3Ti
InChIKey:YONPGGFAJWQGJC-UHFFFAOYSA-K
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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:243.945
Molecular Formula:C8H6Cl4
InChIKey:DTTXIZRMECHQPB-RHAWHZQYSA-N
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Compound Information
Molecular Weight:204.2219
Molecular Formula:C12H12O3
InChIKey:LZNWSTSLSVBRTP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:119.1622
Molecular Formula:C5H13NO2
InChIKey:ZSXGLVDWWRXATF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:92.0938
Molecular Formula:C3H8O3
InChIKey:Not Available
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Compound Information
Molecular Weight:84.1595
Molecular Formula:C6H12
InChIKey:LGAQJENWWYGFSN-PLNGDYQASA-N
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Compound Information
Molecular Weight:277.96
Molecular Formula:C8H8Cl4O2
InChIKey:CZLSDQKJRJFKJL-YXZLLOMISA-N
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Compound Information
Molecular Weight:102.971
Molecular Formula:Cl2S
InChIKey:FWMUJAIKEJWSSY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:162.445
Molecular Formula:C3H6Cl3N
InChIKey:NRNFKRFWZQQDMD-UHFFFAOYSA-M
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Compound Information
Molecular Weight:172.1785
Molecular Formula:C8H12O4
InChIKey:Not Available
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Compound Information
Molecular Weight:138.1638
Molecular Formula:C8H10O2
InChIKey:PWMWNFMRSKOCEY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:39.0983
Molecular Formula:K
InChIKey:NTTOTNSKUYCDAV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:177.284
Molecular Formula:C8H17O2S
InChIKey:POXZHAVYUQSNIT-KHSUWTBESA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:130.1849
Molecular Formula:C7H14O2
InChIKey:JWQDBZRAEVKBEN-BOJSHJERSA-N
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Compound Information
Molecular Weight:272.772
Molecular Formula:C5Cl6
InChIKey:VUNCWTMEJYMOOR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:108.1809
Molecular Formula:C8H12
InChIKey:SSPNLRVPYROWLU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:120.147
Molecular Formula:C5H12O3
InChIKey:WEAYWASEBDOLRG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:58.0791
Molecular Formula:C3H6O
InChIKey:CSCPPACGZOOCGX-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:112.2126
Molecular Formula:C8H16
InChIKey:XTUXVDJHGIEBAA-FPLPWBNLSA-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:144.2114
Molecular Formula:C8H16O2
InChIKey:NBKYHXDYYXTFJU-BOJSHJERSA-N
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Compound Information
Molecular Weight:148.114
Molecular Formula:C5H8O5
InChIKey:CUOKHACJLGPRHD-BXXZVTAOSA-N
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Compound Information
Molecular Weight:318.495
Molecular Formula:C24H30
InChIKey:MVZVDAGWAAZJPE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:128.169
Molecular Formula:C7H12O2
InChIKey:HNMVZUWXQLASRL-CYDAGYADSA-N
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Compound Information
Molecular Weight:104.1045
Molecular Formula:C4H8O3
InChIKey:SSYDTHANSGMJTP-ZXZARUISSA-N
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Compound Information
Molecular Weight:182.2301
Molecular Formula:C5H15O3PSi
InChIKey:HWMXPTIFAGBDIK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:28.0532
Molecular Formula:C2H4
InChIKey:Not Available
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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:132.2007
Molecular Formula:C7H16O2
InChIKey:VUVZASHBYYMLRC-NKWVEPMBSA-N
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Compound Information
Molecular Weight:149.89424
Molecular Formula:INa
InChIKey:FVAUCKIRQBBSSJ-UHFFFAOYSA-M
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Compound Information
Molecular Weight:104.1491
Molecular Formula:C8H8
InChIKey:PPBRXRYQALVLMV-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:65.409
Molecular Formula:Zn
InChIKey:HCHKCACWOHOZIP-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:80.1277
Molecular Formula:C6H8
InChIKey:AFVDZBIIBXWASR-AATRIKPKSA-N
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Compound Information
Molecular Weight:82.1436
Molecular Formula:C6H10
InChIKey:ZLUNIANKFULIMZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:114.1424
Molecular Formula:C6H10O2
InChIKey:KUQWZSZYIQGTHT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:90.121
Molecular Formula:C4H10O2
InChIKey:XTHFKEDIFFGKHM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:104.1045
Molecular Formula:C4H8O3
InChIKey:SSYDTHANSGMJTP-IMJSIDKUSA-N
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Compound Information
Molecular Weight:56.1063
Molecular Formula:C4H8
InChIKey:IAQRGUVFOMOMEM-ONEGZZNKSA-N
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Compound Information
Molecular Weight:90.121
Molecular Formula:C4H10O2
InChIKey:Not Available
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Compound Information
Molecular Weight:90.121
Molecular Formula:C4H10O2
InChIKey:Not Available
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Compound Information
Molecular Weight:56.1063
Molecular Formula:C4H8
InChIKey:IAQRGUVFOMOMEM-ONEGZZNKSA-N
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Compound Information
Molecular Weight:102.1317
Molecular Formula:C5H10O2
InChIKey:VCVOSERVUCJNPR-WHFBIAKZSA-N
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Compound Information
Molecular Weight:80.1277
Molecular Formula:C6H8
InChIKey:AFVDZBIIBXWASR-WAYWQWQTSA-N
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Compound Information
Molecular Weight:116.1583
Molecular Formula:C6H12O2
InChIKey:PFURGBBHAOXLIO-PHDIDXHHSA-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:124.2111
Molecular Formula:C6H14O2
InChIKey:Not Available
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Compound Information
Molecular Weight:90.1965
Molecular Formula:C6H12
InChIKey:Not Available
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Compound Information
Molecular Weight:124.2111
Molecular Formula:C6H14O2
InChIKey:Not Available
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Compound Information
Molecular Weight:90.1965
Molecular Formula:C6H12
InChIKey:Not Available
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Compound Information
Molecular Weight:118.1742
Molecular Formula:C6H14O2
InChIKey:RLWWHEFTJSHFRN-WDSKDSINSA-N
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Compound Information
Molecular Weight:84.1595
Molecular Formula:C6H12
InChIKey:BEQGRRJLJLVQAQ-GQCTYLIASA-N
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Compound Information
Molecular Weight:118.1742
Molecular Formula:C6H14O2
InChIKey:RNKURRDNOYXATR-NTSWFWBYSA-N
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Compound Information
Molecular Weight:84.1595
Molecular Formula:C6H12
InChIKey:LGAQJENWWYGFSN-SNAWJCMRSA-N
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Compound Information
Molecular Weight:118.1742
Molecular Formula:C6H14O2
InChIKey:RNKURRDNOYXATR-PHDIDXHHSA-N
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Compound Information
Molecular Weight:130.1849
Molecular Formula:C7H14O2
InChIKey:IOZFUGDROBQPNP-RNFRBKRXSA-N
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Compound Information
Molecular Weight:132.2007
Molecular Formula:C7H16O2
InChIKey:VUVZASHBYYMLRC-RNFRBKRXSA-N
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Compound Information
Molecular Weight:98.1861
Molecular Formula:C7H14
InChIKey:OTTZHAVKAVGASB-HWKANZROSA-N
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Compound Information
Molecular Weight:206.1932
Molecular Formula:C8H14O6
InChIKey:YSAVZVORKRDODB-OLQVQODUSA-N
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Compound Information
Molecular Weight:172.1785
Molecular Formula:C8H12O4
InChIKey:Not Available
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Compound Information
Molecular Weight:144.2114
Molecular Formula:C8H16O2
InChIKey:HUSOFJYAGDTKSK-OCAPTIKFSA-N
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Compound Information
Molecular Weight:144.2114
Molecular Formula:C8H16O2
InChIKey:HUSOFJYAGDTKSK-YUMQZZPRSA-N
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Compound Information
Molecular Weight:110.1968
Molecular Formula:C8H14
InChIKey:URYYVOIYTNXXBN-OWOJBTEDSA-N
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Compound Information
Molecular Weight:146.2238
Molecular Formula:C8H16O2
InChIKey:Not Available
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Compound Information
Molecular Weight:112.2091
Molecular Formula:C8H14
InChIKey:Not Available
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Compound Information
Molecular Weight:112.2091
Molecular Formula:C8H14
InChIKey:Not Available
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Compound Information
Molecular Weight:112.2126
Molecular Formula:C8H16
InChIKey:ILPBINAXDRFYPL-HYXAFXHYSA-N
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Compound Information
Molecular Weight:146.2273
Molecular Formula:C8H18O2
InChIKey:XMTUJCWABCYSIV-YUMQZZPRSA-N
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Compound Information
Molecular Weight:308.2851
Molecular Formula:C11H20N2O8
InChIKey:LIEXTAHTMBZPAF-OKNNCHMLSA-N
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Compound Information
Molecular Weight:282.2891
Molecular Formula:C14H18O6
InChIKey:VVSWDMJYIDBTMV-ORWNZLQRSA-N
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Compound Information
Molecular Weight:282.5368
Molecular Formula:C17H34OSi
InChIKey:ZPCWLMWFRBSJMR-BUHFOSPRSA-N
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Compound Information
Molecular Weight:234.2463
Molecular Formula:C10H18O6
InChIKey:UHXMUDFLKWDAGN-HFYYSOHNSA-N
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Compound Information
Molecular Weight:152.1904
Molecular Formula:C9H12O2
InChIKey:AYFITXXXKCZALT-NUDGYGSGSA-N
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Compound Information
Molecular Weight:204.2219
Molecular Formula:C12H12O3
InChIKey:HTSRAUGLDNWFOF-NSHDSACASA-N
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Compound Information
Molecular Weight:238.2366
Molecular Formula:C12H14O5
InChIKey:AJNNHEUSPPQEDM-GMTAPVOTSA-N
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Compound Information
Molecular Weight:162.94
Molecular Formula:C2H5Cl2O2P
InChIKey:YZBOZNXACBQJHI-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:188.287
Molecular Formula:C9H16O2S
InChIKey:LIDUMFPWPMLPJP-NFXAZMQOSA-N
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Compound Information
Molecular Weight:348.3026
Molecular Formula:C14H20O10
InChIKey:ZQLBHQSQMQLFBM-XNBXPENISA-N
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Compound Information
Molecular Weight:360.4855
Molecular Formula:C19H36O6
InChIKey:XCFUBHITRBTHAH-MSOLQXFVSA-N
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Compound Information
Molecular Weight:200.2747
Molecular Formula:C11H20O3
InChIKey:NQQVEHXCDAHESB-MXWKQRLJSA-N
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Compound Information
Molecular Weight:316.5514
Molecular Formula:C17H36O3Si
InChIKey:YIXAHBYHMNNSDC-HMUVLFPJSA-N
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Compound Information
Molecular Weight:192.2542
Molecular Formula:C12H16O2
InChIKey:QPEQUWINSFQFTB-KKOKHZNYSA-N
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Compound Information
Molecular Weight:170.2487
Molecular Formula:C10H18O2
InChIKey:WHVGOCCZWVVJTC-AOOOYVTPSA-N
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Compound Information
Molecular Weight:296.3603
Molecular Formula:C19H20O3
InChIKey:RWLCFEKJZDRTFX-RTBURBONSA-N
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Compound Information
Molecular Weight:196.2445
Molecular Formula:C14H12O
InChIKey:OTKCEEWUXHVZQI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:280.3609
Molecular Formula:C19H20O2
InChIKey:JFPWOMOGZNTYSH-VMPITWQZSA-N
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Compound Information
Molecular Weight:134.1736
Molecular Formula:C6H14O3
InChIKey:SBZXBUIDTXKZTM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:200.2316
Molecular Formula:C10H16O4
InChIKey:UGUGKJWRGVNGJJ-BZNPZCIMSA-N
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Compound Information
Molecular Weight:296.4879
Molecular Formula:C19H36O2
InChIKey:QYDYPVFESGNLHU-ZHACJKMWSA-N
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Compound Information
Molecular Weight:174.2805
Molecular Formula:C10H22O2
InChIKey:FUGIIBWTNARRSF-AOOOYVTPSA-N
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Compound Information
Molecular Weight:164.2872
Molecular Formula:C12H20
InChIKey:FJHVMZDLYBHASM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:474.75
Molecular Formula:Cl6K2W
InChIKey:GGTCFCRCVCBPCQ-UHFFFAOYSA-H
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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:134.2182
Molecular Formula:C10H14
InChIKey:DFNKMHNASPGWAY-BECAKDQMSA-N
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Compound Information
Molecular Weight:310.3423
Molecular Formula:C16H22O6
InChIKey:NKCNUNUEQRYLNZ-VQJWOFKYSA-N
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Compound Information
Molecular Weight:17.0305
Molecular Formula:H3N
InChIKey:QGZKDVFQNNGYKY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:170.2487
Molecular Formula:C10H18O2
InChIKey:IYRZZSKRQNSOTP-RMKNXTFCSA-N
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Compound Information
Molecular Weight:166.3031
Molecular Formula:C12H22
InChIKey:HYPABJGVBDSCIT-UPHRSURJSA-N
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Compound Information
Molecular Weight:156.2237
Molecular Formula:C12H12
InChIKey:VYXKGSGHMAIJLR-OYMHRQQLSA-N
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Compound Information
Molecular Weight:251.2817
Molecular Formula:C12H17N3O3
InChIKey:RYCSBVNUERPNNO-LMLFDSFASA-N
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Compound Information
Molecular Weight:170.2487
Molecular Formula:C10H18O2
InChIKey:AYEOSGBMQHXVER-NSDNXHHOSA-N
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Compound Information
Molecular Weight:156.2221
Molecular Formula:C9H16O2
InChIKey:YFXRPWRVFHWHPK-ASIUWFKXSA-N
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Compound Information
Molecular Weight:258.3538
Molecular Formula:C14H26O4
InChIKey:DQORBBZJHOOPKG-CSKARUKUSA-N
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Compound Information
Molecular Weight:232.3196
Molecular Formula:C18H16
InChIKey:BOBLSBAZCVBABY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:164.2011
Molecular Formula:C10H12O2
InChIKey:FFFIRKXTFQCCKJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:180.2451
Molecular Formula:C14H12
InChIKey:PJANXHGTPQOBST-QXMHVHEDSA-N
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Compound Information
Molecular Weight:314.2879
Molecular Formula:C14H18O8
InChIKey:REXNPDYWUANMIX-IGQOVBAYSA-N
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Compound Information
Molecular Weight:234.3355
Molecular Formula:C18H18
InChIKey:MFDMOFOUVPINDU-DCVNBTNUSA-N
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Compound Information
Molecular Weight:136.234
Molecular Formula:C10H16
InChIKey:KUKRLSJNTMLPPK-WCBMZHEXSA-N
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Compound Information
Molecular Weight:180.2451
Molecular Formula:C14H12
InChIKey:XPUFPFFAQIJKNL-LLZFXZEUSA-N
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Compound Information
Molecular Weight:326.4709
Molecular Formula:C19H34O4
InChIKey:JCJBHPDRFZQWRO-HYXAFXHYSA-N
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Compound Information
Molecular Weight:204.2649
Molecular Formula:C13H16O2
InChIKey:ZEJZANDYGUGCQE-CHWSQXEVSA-N
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Compound Information
Molecular Weight:164.2441
Molecular Formula:C11H16O
InChIKey:OVGORFFCBUIFIA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:256.3395
Molecular Formula:C17H20O2
InChIKey:CIIODFLMEGKVDU-DLBZAZTESA-N
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Compound Information
Molecular Weight:393.7321
Molecular Formula:CHI3
InChIKey:OKJPEAGHQZHRQV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:68.0773
Molecular Formula:C3H4N2
InChIKey:RAXXELZNTBOGNW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:136.234
Molecular Formula:C10H16
InChIKey:IHPKGUQCSIINRJ-CSKARUKUSA-N
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Compound Information
Molecular Weight:290.3542
Molecular Formula:C17H22O4
InChIKey:PLNYWGHOYDEIHQ-ZMKYACIDSA-N
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Compound Information
Molecular Weight:140.2658
Molecular Formula:C10H20
InChIKey:YKNMBTZOEVIJCM-HYXAFXHYSA-N
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Compound Information
Molecular Weight:58.6934
Molecular Formula:Ni
InChIKey:PXHVJJICTQNCMI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:144.08
Molecular Formula:CKNSe
InChIKey:KYEKHFSRAXRJBR-UHFFFAOYSA-M
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Compound Information
Molecular Weight:118.1757
Molecular Formula:C9H10
InChIKey:FQCISEZKCHBFSX-SPJNRGJMSA-N
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Compound Information
Molecular Weight:294.474
Molecular Formula:C13H26O3S2
InChIKey:OKSMNUIJVINMSY-IJLUTSLNSA-N
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Compound Information
Molecular Weight:255.517
Molecular Formula:C6H4BrClO2S
InChIKey:KMMHZIBWCXYAAH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:198.3019
Molecular Formula:C12H22O2
InChIKey:AHXIONNOXQTDNQ-VQHVLOKHSA-N
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Compound Information
Molecular Weight:194.2133
Molecular Formula:C10H15N2P
InChIKey:CYKFZCQRONDMOZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:170.7338
Molecular Formula:C4NiO4
InChIKey:AWDHUGLHGCVIEG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:122.1677
Molecular Formula:C7H10N2
InChIKey:VHYFNPMBLIVWCW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:253.80894
Molecular Formula:I2
InChIKey:PNDPGZBMCMUPRI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:138.2499
Molecular Formula:C10H18
InChIKey:UCIYGNATMHQYCT-UPHRSURJSA-N
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