Standard Article

Ketene Cycloadditions

  1. John A. Hyatt,
  2. Peter W. Raynolds

Published Online: 15 OCT 2004

DOI: 10.1002/0471264180.or045.02

Organic Reactions

Organic Reactions

How to Cite

Hyatt, J. A. and Raynolds, P. W. 2004. Ketene Cycloadditions. Organic Reactions. 45:2:159–646.

Author Information

  1. Eastman Chemical Co., Research Laboratories, Kingsport, Tennessee

Publication History

  1. Published Online: 15 OCT 2004

Chemistry Terms

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Abstract

The reaction of ketene with itself was described almost simultaneously in 1908 by Chick and Wilsmore in England, and by Staudinger and Klever in Germany; priority for the discovery was attributed to Wilsmore by the German group.

Ketene cycloaddition was an early example of a peculiar process, one that formed carbon–carbon bonds with ease, often without the need for solvent, catalyst, or high heat. Subsequent work by others was done in the shadow of Staudinger's exhaustive and rigorous study of all phases of ketene reactivity. Three factors led to a resurgence of interest in this reaction beginning in the 1960s. Haloketenes, which had previously eluded study, were found to have high reactivity, and the halogens could easily be removed after the reaction. The increasing sophistication of powerful analytical methods, particularly nuclear magnetic resonance spectroscopy, led to discovery of the interesting stereochemical aspects of this reaction. Finally, the new theory of orbital symmetry conservation provided a conceptual framework to rationalize these puzzling “no mechanism” reactions.

This chapter is a review of cycloaddition reactions of ketenes. Here, a cycloaddition is defined as a reaction of a ketene with an unsaturated organic compound to give a cyclic product by a mechanism that, in principle, involves the almost simultaneous formation of two bonds between two reactants. While there is no concern here as to whether bond formation is concerted or stepwise, no other chemical process can take place between the formation of the first and second bond. Definition here involves both structural and mechanistic factors, and it is difficult to avoid a certain amount of arbitrariness. Products, such as dehydroacetic acid, which seem to us to arise by concatenation of ketene molecules followed by cyclization are excluded. These reactions, are more properly considered to arise from a series of ionic reactions, and the prediction of the eventual product does not take advantage of the special mechanistic features commonly associated with true cycloadditions. Additions to imines to give β-lactams are numerous and will be covered in a separate review. The literature has been searched to the end of 1988.

Many reviews devoted partially or exclusively to ketene cycloadditions have been published. Specific topics that have been reviewed include haloketenes, fluoroketenes, cyanoketenes, intramolecular cycloadditions, conjugated ketenes, and β-lactam antibiotics. Ancillary topics pertinent to ketene cycloadditions that have been reviewed include cycloreversion reactions, ketene equivalents, which provide ketene functionality with olefin-like reactivity especially in [4 + 2] reactions, application of frontier molecular orbital theory to cycloadditions, and a critical discussion of cycloadditions with polar intermediates. Applications of cyclobutanones in synthesis have also been reviewed.

Keywords:

  • ketene cycloadditions;
  • cycloadditions;
  • acylketenes;
  • vinyl ketenes;
  • alpha, beta-unsaturated ketones;
  • alpha, beta-unsaturated thiones;
  • acyl isocyanates;
  • acyl azo compounds;
  • thioacyl imines;
  • thiacyl imines;
  • mesionic compounds;
  • experimental procedures;
  • scope;
  • limitations;
  • dienes;
  • azadienes;
  • amidines;
  • o-quinones;
  • heterocumulenes;
  • azo compounds

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Compound Information
Molecular Weight:0
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:252.3923
Molecular Formula:C16H28O2
InChIKey:LIGSTRZKISALTK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:152.963
Molecular Formula:C4H2Cl2O2
InChIKey:LULQZXIYRUTJDL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:444.4759
Molecular Formula:C27H24O6
InChIKey:RCXAMWBQUKCBMY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:360.401
Molecular Formula:C20H24O6
InChIKey:UZZUPNFJQSOSDU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:164.2011
Molecular Formula:C10H12O2
InChIKey:RNLGDQGIPVGFGQ-YVMONPNESA-N
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Compound Information
Molecular Weight:120.577
Molecular Formula:C5H9ClO
InChIKey:XGISHOFUAFNYQF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:138.1638
Molecular Formula:C8H10O2
InChIKey:JFWCNIBCXSXTIN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:354.3979
Molecular Formula:C24H18O3
InChIKey:VRGWLIUHHHKEGB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:209.07
Molecular Formula:C8H10Cl2O2
InChIKey:HXTYZWJVMWWWDK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:132.588
Molecular Formula:C6H9ClO
InChIKey:WEPUZBYKXNKSDH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:477.4245
Molecular Formula:C27H15N3O6
InChIKey:FIQFAODKLCEYRB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:123.1525
Molecular Formula:C7H9NO
InChIKey:PXMIEOACHDWJQE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:196.673
Molecular Formula:C11H13ClO
InChIKey:CUSBVJLSOMXCBJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:348.3918
Molecular Formula:C22H20O4
InChIKey:HDLOCUCUURYCNE-NTCAYCPXSA-N
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Compound Information
Molecular Weight:96.1271
Molecular Formula:C6H8O
InChIKey:ONUICCDUQUPKLA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:436.1068
Molecular Formula:C12F12O4
InChIKey:JIVLZNNZOMZPPM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:70.0898
Molecular Formula:C4H6O
InChIKey:VDOKWPVSGXHSNP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:144.1032
Molecular Formula:C7H5NaO2
InChIKey:WXMKPNITSTVMEF-UHFFFAOYSA-M
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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:130.1418
Molecular Formula:C6H10O3
InChIKey:WYVAMUWZEOHJOQ-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:356.0652
Molecular Formula:C8F12O2
InChIKey:MXJOVROEOLXOAN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:134.604
Molecular Formula:C6H11ClO
InChIKey:YWGHUJQYGPDNKT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:246.3049
Molecular Formula:C14H18N2O2
InChIKey:MGKVNSDJNQKCGP-KTKRTIGZSA-N
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Compound Information
Molecular Weight:140.1797
Molecular Formula:C8H12O2
InChIKey:DYKOGWMQOXNHDP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:272.2958
Molecular Formula:C16H16O4
InChIKey:UGCKADBZMQTJGI-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:168.1898
Molecular Formula:C9H12O3
InChIKey:UXDUBTRIJHHLDL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:229.898
Molecular Formula:C4H6Br2O
InChIKey:HHKDBXNYWNUHPL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:88.1283
Molecular Formula:C4H10NO
InChIKey:FVCOIAYSJZGECG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:133.341
Molecular Formula:AlCl3
InChIKey:VSCWAEJMTAWNJL-UHFFFAOYSA-K
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Compound Information
Molecular Weight:188.651
Molecular Formula:C9H13ClO2
InChIKey:QIHPBZZFQAMBMZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:164.2011
Molecular Formula:C10H12O2
InChIKey:QUKJDEISKNBWDR-YVMONPNESA-N
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Compound Information
Molecular Weight:152.963
Molecular Formula:C4H2Cl2O2
InChIKey:KILQGQFRJBMRBW-UPHRSURJSA-N
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Compound Information
Molecular Weight:277.585
Molecular Formula:C11H14BrClO
InChIKey:FVXWPEQCFKTWJT-GSYHAUMWSA-N
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Compound Information
Molecular Weight:140.1797
Molecular Formula:C8H12O2
InChIKey:OKAAPXFKYOTAEN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:92.524
Molecular Formula:C3H5ClO
InChIKey:Not Available
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Compound Information
Molecular Weight:192.2542
Molecular Formula:C12H16O2
InChIKey:TUECSRVQKHJHMP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:544.5917
Molecular Formula:C32H32O8
InChIKey:QHXRKLUBGDCBMB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:211.086
Molecular Formula:C8H12Cl2O2
InChIKey:PUIBKAHUQOOLSW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:320.4248
Molecular Formula:C22H24O2
InChIKey:RHLWVJKSMFPRLK-SZPZYZBQSA-N
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Compound Information
Molecular Weight:201.845
Molecular Formula:C2H2Br2O
InChIKey:Not Available
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Compound Information
Molecular Weight:252.3493
Molecular Formula:C15H24O3
InChIKey:SKJMYLKHNBQDCR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:146.1858
Molecular Formula:C10H10O
InChIKey:XLINTHZLBFGDAD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:196.286
Molecular Formula:C12H20O2
InChIKey:MJZLRAHODCHJCG-LUAWRHEFSA-N
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Compound Information
Molecular Weight:168.2328
Molecular Formula:C10H16O2
InChIKey:QLGNMKTXRQMIMH-YVMONPNESA-N
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Compound Information
Molecular Weight:284.3081
Molecular Formula:C20H12O2
InChIKey:AUZPINQLIPXVTP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:215.871
Molecular Formula:C3H4Br2O
InChIKey:ILLHORFDXDLILE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:158.625
Molecular Formula:C8H11ClO
InChIKey:RPWMIEJSNOFWTC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:248.3606
Molecular Formula:C16H24O2
InChIKey:MPMXLVXUVYZHBE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:106.551
Molecular Formula:C4H7ClO
InChIKey:DGMOBVGABMBZSB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:244.3288
Molecular Formula:C16H20O2
InChIKey:XCWBQGUMJKKDHB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:218.2054
Molecular Formula:C12H10O4
InChIKey:RMTJGYMSXVRJEA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:512.1005
Molecular Formula:C12F16O4
InChIKey:DIWLARQRHWJTRO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:356.0652
Molecular Formula:C8F12O2
InChIKey:FNXJSVSBVBZZKO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:151.9038551
Molecular Formula:CsF
InChIKey:XJHCXCQVJFPJIK-UHFFFAOYSA-M
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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:112.943
Molecular Formula:C2H2Cl2O
InChIKey:VGCXGMAHQTYDJK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:196.286
Molecular Formula:C12H20O2
InChIKey:ZXNNSNWXWTXRBG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:84.0734
Molecular Formula:C4H4O2
InChIKey:PZQGSZRQKQZCOJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:248.3606
Molecular Formula:C16H24O2
InChIKey:VPEUXMXNOPBZDU-KAMYIIQDSA-N
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Compound Information
Molecular Weight:178.0326
Molecular Formula:C4F6O
InChIKey:ZJOKQELGBASVKR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:320.4248
Molecular Formula:C22H24O2
InChIKey:IXXLXXZYWFZXQB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:160.641
Molecular Formula:C8H13ClO
InChIKey:VABYVFZVTIDNOA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:195.602
Molecular Formula:C9H6ClNO2
InChIKey:WWUNZQKHHWETGJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:120.577
Molecular Formula:C5H9ClO
InChIKey:Not Available
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Molecular Weight:146.615
Molecular Formula:C7H11ClO
InChIKey:RVOJTCZRIKWHDX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:136.315
Molecular Formula:Cl2Zn
InChIKey:Not Available
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Molecular Weight:244.3288
Molecular Formula:C16H20O2
InChIKey:NLEJMYIDTBUARH-UHFFFAOYSA-N
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Molecular Weight:244.3288
Molecular Formula:C16H20O2
InChIKey:MZPLZAULPFAEHN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:272.382
Molecular Formula:C18H24O2
InChIKey:DLKJHJODXUITMD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:68.074
Molecular Formula:C4H4O
InChIKey:XGIVOKYSENAIBM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:98.143
Molecular Formula:C6H10O
InChIKey:NWXORMWIWGSYJJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:172.652
Molecular Formula:C9H13ClO
InChIKey:CHBNNQBNTWGRKN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:136.1479
Molecular Formula:C8H8O2
InChIKey:VQIUDMMYMVRNLG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:186.679
Molecular Formula:C10H15ClO
InChIKey:RMBIEFVLEGANCN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:122.1644
Molecular Formula:C8H10O
InChIKey:VCISMABSBPXZPH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:304.3808
Molecular Formula:C18H24O4
InChIKey:WRPGVFJVYAEGDS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:256.0502
Molecular Formula:C6F8O2
InChIKey:AZTFVXMLMYXUJS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:162.657
Molecular Formula:C8H15ClO
InChIKey:REEZZSHJLXOIHL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:150.1778
Molecular Formula:C8H10N2O
InChIKey:NLKPDSAHCYSQMD-OLQVQODUSA-N
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Compound Information
Molecular Weight:355.688
Molecular Formula:C6Cl8
InChIKey:WNYCWKSFQDZCCY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:214.689
Molecular Formula:C11H15ClO2
InChIKey:BJFLBFJZUJVICY-AMXGMDGSSA-N
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Compound Information
Molecular Weight:112.1265
Molecular Formula:C6H8O2
InChIKey:ZSADIOZWRMCYNY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:216.661
Molecular Formula:C10H13ClO3
InChIKey:LWXFPFKFZNHICP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:680.7396
Molecular Formula:C40H40O10
InChIKey:PQMBZYPQSVLGNX-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:220.3074
Molecular Formula:C14H20O2
InChIKey:NQCABGRZRRCWPC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:118.561
Molecular Formula:C5H7ClO
InChIKey:JFWMYCVMQSLLOO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:252.3923
Molecular Formula:C16H28O2
InChIKey:ABJWZTIYAYNKFO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:112.1265
Molecular Formula:C6H8O2
InChIKey:CMSUQAHYZQWEKF-HYXAFXHYSA-N
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Compound Information
Molecular Weight:158.195
Molecular Formula:C8H14O3
InChIKey:YHASWHZGWUONAO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:168.2328
Molecular Formula:C10H16O2
InChIKey:DQQJQHVAPGGXHF-CLFYSBASSA-N
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Compound Information
Molecular Weight:300.4351
Molecular Formula:C20H28O2
InChIKey:NWVFECKAEHXRFR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:152.1919
Molecular Formula:C12H8
InChIKey:HXGDTGSAIMULJN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:170.1626
Molecular Formula:C8H10O4
InChIKey:AXJVPXNVESYGDT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:241.865
Molecular Formula:C4H2Br2O2
InChIKey:VCQSHQJGNVPOCA-UPHRSURJSA-N
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Compound Information
Molecular Weight:196.673
Molecular Formula:C11H13ClO
InChIKey:HHZACHCTBBRYEB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:154.594
Molecular Formula:C8H7ClO
InChIKey:Not Available
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Compound Information
Molecular Weight:220.2213
Molecular Formula:C12H12O4
InChIKey:DESNERTWJQDLQR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:84.0734
Molecular Formula:C4H4O2
InChIKey:WASQWSOJHCZDFK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:86.1754
Molecular Formula:C6H14
InChIKey:VLKZOEOYAKHREP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:239.537
Molecular Formula:C8H12BrClO
InChIKey:KCJDLFNKGINOPR-UHFFFAOYSA-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:183.033
Molecular Formula:C6H8Cl2O2
InChIKey:PWAXUOGZOSVGBO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:170.1674
Molecular Formula:C10H6N2O
InChIKey:URQUNWYOBNUYJQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:252.3923
Molecular Formula:C16H28O2
InChIKey:PSSKZWOEKWIMCZ-SQFISAMPSA-N
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Compound Information
Molecular Weight:408.4438
Molecular Formula:C24H24O6
InChIKey:VGHJZITXHPJPPI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:140.2227
Molecular Formula:C9H16O
InChIKey:FRUPMOJDDIVAIQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:436.4108
Molecular Formula:C24H20O8
InChIKey:DKGXDBFVGUBPSB-NHDPSOOVSA-N
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Compound Information
Molecular Weight:60.1182
Molecular Formula:C3H9N
InChIKey:GETQZCLCWQTVFV-UHFFFAOYSA-O
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Compound Information
Molecular Weight:107.1531
Molecular Formula:C7H9N
InChIKey:Not Available
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Compound Information
Molecular Weight:189.039
Molecular Formula:C8H6Cl2O
InChIKey:FGEAOSXMQZWHIQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:184.62
Molecular Formula:C9H9ClO2
InChIKey:CXJOONIFSVSFAD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:184.1892
Molecular Formula:C9H12O4
InChIKey:BCBIRSMSEPXOLY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:246.3032
Molecular Formula:C18H14O
InChIKey:LHMGUPFCUBAFSV-IYBDPMFKSA-N
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Compound Information
Molecular Weight:220.2213
Molecular Formula:C12H12O4
InChIKey:MCCLMTWMSSBBRV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:136.1479
Molecular Formula:C8H8O2
InChIKey:CMDGYJSBBVWRJC-QPJJXVBHSA-N
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Compound Information
Molecular Weight:118.561
Molecular Formula:C5H7ClO
InChIKey:IALGRRFZGRXFKT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:292.3716
Molecular Formula:C20H20O2
InChIKey:WRXLROZOOJNTQS-BGYRXZFFSA-N
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Compound Information
Molecular Weight:236.2653
Molecular Formula:C16H12O2
InChIKey:QGEIKMOHJVAECU-KAMYIIQDSA-N
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Compound Information
Molecular Weight:182.647
Molecular Formula:C10H11ClO
InChIKey:OWAWAFKVPTWIBP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:182.647
Molecular Formula:C10H11ClO
InChIKey:QGXMHCMPIAYMGT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:72.1057
Molecular Formula:C4H8O
InChIKey:WYURNTSHIVDZCO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:192.2542
Molecular Formula:C12H16O2
InChIKey:KJAIMMOVXNSJLB-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:222.2787
Molecular Formula:C10H22O5
InChIKey:ZUHZGEOKBKGPSW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:324.4565
Molecular Formula:C22H28O2
InChIKey:MZXRRJSFHIXKEN-RTNDPHFSSA-N
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Compound Information
Molecular Weight:188.694
Molecular Formula:C10H17ClO
InChIKey:YJNINJXESSDLSJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:264.3184
Molecular Formula:C18H16O2
InChIKey:UJHGRKVJAVUZDY-IYARVYRRSA-N
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Compound Information
Molecular Weight:296.3172
Molecular Formula:C18H16O4
InChIKey:GHBPUKKZHCDKRZ-WJDWOHSUSA-N
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Compound Information
Molecular Weight:210.2695
Molecular Formula:C12H18O3
InChIKey:ZPTFQBBMPKSAKY-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:134.604
Molecular Formula:C6H11ClO
InChIKey:BUTKIHRNYUEGKB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:211.484
Molecular Formula:C6H8BrClO
InChIKey:IGSJTKTYFZFEFT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:292.3716
Molecular Formula:C20H20O2
InChIKey:QHWFEXMTOZTLOP-BGYRXZFFSA-N
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Compound Information
Molecular Weight:256.4888
Molecular Formula:C12H24O2Si2
InChIKey:ZNNBRDVJEFASTP-XFFZJAGNSA-N
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Compound Information
Molecular Weight:237.521
Molecular Formula:C8H10BrClO
InChIKey:NOZICQCPLPRINB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:126.1962
Molecular Formula:C8H14O
InChIKey:RXVMCPFWIXNUBL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:156.1791
Molecular Formula:C8H12O3
InChIKey:LFSVADABIDBSBV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:160.641
Molecular Formula:C8H13ClO
InChIKey:CIYPNZYEUZQIHN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:168.62
Molecular Formula:C9H9ClO
InChIKey:FOTITZRWZUAVPH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:302.3251
Molecular Formula:C16H18N2O4
InChIKey:NEMSXVGTHJHAPO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:42.0367
Molecular Formula:C2H2O
InChIKey:CCGKOQOJPYTBIH-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:210.2695
Molecular Formula:C12H18O3
InChIKey:DXLKLICKNIROHG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:140.1797
Molecular Formula:C8H12O2
InChIKey:RGCDVHNITQEYPO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:164.705
Molecular Formula:C6H13ClOSi
InChIKey:JOLXPNFNBVPESL-UHFFFAOYSA-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:196.286
Molecular Formula:C12H20O2
InChIKey:BTPBFEPVFFQWKK-FPLPWBNLSA-N
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Compound Information
Molecular Weight:244.3288
Molecular Formula:C16H20O2
InChIKey:AODNQYGHDCNEII-ULKKZQANSA-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:140.1797
Molecular Formula:C8H12O2
InChIKey:OFSRUBQYHGLZMT-ALCCZGGFSA-N
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Compound Information
Molecular Weight:164.2011
Molecular Formula:C10H12O2
InChIKey:VFHGYGWDEXAIAE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:192.2542
Molecular Formula:C12H16O2
InChIKey:AVGUIOFWMBMPGE-HAQNSBGRSA-N
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Compound Information
Molecular Weight:254.666
Molecular Formula:C12H11ClO4
InChIKey:SDIIFGKUGXNKJR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:106.551
Molecular Formula:C4H7ClO
InChIKey:DVECBJCOGJRVPX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:304.4669
Molecular Formula:C20H32O2
InChIKey:XGXLWTCABQCYPT-UYRXBGFRSA-N
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Compound Information
Molecular Weight:173.277
Molecular Formula:AgZn
InChIKey:BSWGGJHLVUUXTL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:186.2481
Molecular Formula:C10H18O3
InChIKey:FREZLSIGWNCSOQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:187.624
Molecular Formula:C8H10ClNO2
InChIKey:XVMLWFUWKQJQEY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:63.546
Molecular Formula:Cu
InChIKey:RYGMFSIKBFXOCR-UHFFFAOYSA-N
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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:118.561
Molecular Formula:C5H7ClO
InChIKey:BDUBTLFQHNYXPC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:147.388
Molecular Formula:C2HCl3O
InChIKey:FBCCMZVIWNDFMO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:248.3606
Molecular Formula:C16H24O2
InChIKey:VFOXSWMRLDDTAY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:264.3184
Molecular Formula:C18H16O2
InChIKey:UJHGRKVJAVUZDY-HDICACEKSA-N
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Compound Information
Molecular Weight:292.3716
Molecular Formula:C20H20O2
InChIKey:WRXLROZOOJNTQS-MXVIHJGJSA-N
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Compound Information
Molecular Weight:292.3716
Molecular Formula:C20H20O2
InChIKey:QHWFEXMTOZTLOP-MXVIHJGJSA-N
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Compound Information
Molecular Weight:292.3716
Molecular Formula:C20H20O2
InChIKey:WRXLROZOOJNTQS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:320.4248
Molecular Formula:C22H24O2
InChIKey:RHLWVJKSMFPRLK-HZCBDIJESA-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:185.651
Molecular Formula:C9H12ClNO
InChIKey:BOAUYHJBWVUGPW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:532.9239
Molecular Formula:C36H68O2
InChIKey:NGDLSKPZMOTRTR-OAPYJULQSA-N
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Compound Information
Molecular Weight:278.3881
Molecular Formula:C20H22O
InChIKey:NFFXVSRCZKDGMT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:166.26
Molecular Formula:C11H18O
InChIKey:GJBHCOJCIQGZOV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:236.3083
Molecular Formula:C17H16O
InChIKey:WIRMNOOOMFTFEQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:68.117
Molecular Formula:C5H8
InChIKey:QIRVGKYPAOQVNP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:126.969
Molecular Formula:C3H4Cl2O
InChIKey:JEQDSBVHLKBEIZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:380.5628
Molecular Formula:C26H36O2
InChIKey:HJXJRSSEPGLQBN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:250.2488
Molecular Formula:C16H10O3
InChIKey:NQMCLTYFIJFWJE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:416.5104
Molecular Formula:C30H24O2
InChIKey:CZMRCWWTKQWFLI-RNPORBBMSA-N
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Compound Information
Molecular Weight:234.1389
Molecular Formula:C8H8F6O
InChIKey:PFRAUJHIEJDCQU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:420.7113
Molecular Formula:C28H52O2
InChIKey:KFZQEDMTUMUCCC-RFBIWTDZSA-N
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Compound Information
Molecular Weight:540.8183
Molecular Formula:C38H52O2
InChIKey:VLYFVUBFKLKHQO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:165.1891
Molecular Formula:C9H11NO2
InChIKey:VQQRWSYIKCJQTD-SREVYHEPSA-N
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Compound Information
Molecular Weight:202.678
Molecular Formula:C10H15ClO2
InChIKey:CQBJRZCQOPGSIP-SREVYHEPSA-N
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Compound Information
Molecular Weight:460.6906
Molecular Formula:C32H44O2
InChIKey:RZGDFSPITZEZNP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:204.769
Molecular Formula:C9H17ClOSi
InChIKey:VOLNBXXFZHFIPD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:213.06
Molecular Formula:C10H6Cl2O
InChIKey:JQIUAKCMZXIOFM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:180.2866
Molecular Formula:C12H20O
InChIKey:NJDFTXQKBBFAQY-PWSUYJOCSA-N
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Compound Information
Molecular Weight:253.3804
Molecular Formula:C15H27NO2
InChIKey:NDABHUGWXUJPPN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:179.2588
Molecular Formula:C11H17NO
InChIKey:MMQNFNPBNVLVGO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:68.117
Molecular Formula:C5H8
InChIKey:YIWFBNMYFYINAD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:140.2227
Molecular Formula:C9H16O
InChIKey:YFGKCGOSAVOMJE-NKWVEPMBSA-N
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Compound Information
Molecular Weight:250.3349
Molecular Formula:C18H18O
InChIKey:KDHQIZIEJKPXJF-KGLIPLIRSA-N
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Compound Information
Molecular Weight:352.5097
Molecular Formula:C24H32O2
InChIKey:LPXLZGPLQOOCRW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:207.2689
Molecular Formula:C12H17NO2
InChIKey:LQBYDVBHMHVNTC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:56.0633
Molecular Formula:C3H4O
InChIKey:UYLUJGRCKKSWHS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:82.1436
Molecular Formula:C6H10
InChIKey:MKPHNILWOMCVTH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:179.044
Molecular Formula:C7H8Cl2O
InChIKey:ZHEGZTCKKDJSHF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:171.42
Molecular Formula:C3H4BrClO
InChIKey:OZGMODDEIHYPRY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:214.3767
Molecular Formula:C11H22O2Si
InChIKey:RDYRYLKTLRLQHH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:152.2334
Molecular Formula:C10H16O
InChIKey:IWDHEHNCMWFIJH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:312.1565
Molecular Formula:C10H8F8O2
InChIKey:LRDADFRQTUBAMW-ONEGZZNKSA-N
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Compound Information
Molecular Weight:304.3392
Molecular Formula:C20H16O3
InChIKey:OMYXVVLNTDPUON-UHFFFAOYSA-N
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Compound Information
Molecular Weight:312.1565
Molecular Formula:C10H8F8O2
InChIKey:AXEYTUANVRMCJY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:188.651
Molecular Formula:C9H13ClO2
InChIKey:UVXYZMVSRAKJPI-WAYWQWQTSA-N
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Compound Information
Molecular Weight:388.4572
Molecular Formula:C28H20O2
InChIKey:NVNAGLLAVVYIAI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:211.3437
Molecular Formula:C13H25NO
InChIKey:BFOUNEYGGJHCBG-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:170.2487
Molecular Formula:C10H18O2
InChIKey:SMMMCYDINLOUID-UHFFFAOYSA-N
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Compound Information
Molecular Weight:246.817
Molecular Formula:C14H27ClO
InChIKey:Not Available
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Compound Information
Molecular Weight:84.1595
Molecular Formula:C6H12
InChIKey:LIKMAJRDDDTEIG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:214.689
Molecular Formula:C11H15ClO2
InChIKey:RUWZEKFIUDVSSH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:202.721
Molecular Formula:C11H19ClO
InChIKey:KGAZHHPYIJCKFU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:98.1861
Molecular Formula:C7H14
InChIKey:Not Available
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Compound Information
Molecular Weight:152.2334
Molecular Formula:C10H16O
InChIKey:NLQALFPDAXMFIM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:179.2588
Molecular Formula:C11H17NO
InChIKey:AXXGZCIICZORRY-IXIJJPBFSA-N
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Compound Information
Molecular Weight:476.8176
Molecular Formula:C32H60O2
InChIKey:BKSVJFGDPOUPBY-YCNYHXFESA-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:96.1702
Molecular Formula:C7H12
InChIKey:UEVOQCSGNIHNLH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:275.182
Molecular Formula:C12H19BrO2
InChIKey:LGLJWFBVSUIDER-CMDGGOBGSA-N
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Compound Information
Molecular Weight:94.517
Molecular Formula:C3H5ClO
InChIKey:RZWZRACFZGVKFM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:276.3722
Molecular Formula:C20H20O
InChIKey:RJZIQWHPORLELZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:140.996
Molecular Formula:C4H6Cl2O
InChIKey:KVQJVAOMYWTLEO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:266.806
Molecular Formula:C16H23ClO
InChIKey:WBVNYYPXQVVOAX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:298.13
Molecular Formula:C9H6F8O2
InChIKey:YHFFACBKSLERRG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:185.651
Molecular Formula:C9H12ClNO
InChIKey:CTTWEUDIJTXTTN-FJXKBIBVSA-N
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Compound Information
Molecular Weight:184.252
Molecular Formula:C11H18O2
InChIKey:YGGLBKISWWMKTG-NTMALXAHSA-N
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Compound Information
Molecular Weight:234.1389
Molecular Formula:C8H8F6O
InChIKey:IORDNIQTCGELAV-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:172.652
Molecular Formula:C9H13ClO
InChIKey:XHJJXFGSVRCMLW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:171.624
Molecular Formula:C8H10ClNO
InChIKey:FGQUCVYRIVCMKJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:220.1124
Molecular Formula:C7H6F6O
InChIKey:JPERQGFCHMRJQF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:202.678
Molecular Formula:C10H15ClO2
InChIKey:NVJJHCCWHWYLPW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:244.716
Molecular Formula:C15H13ClO
InChIKey:HRASKBHYJSRIJW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:142.1956
Molecular Formula:C8H14O2
InChIKey:OUACYWJQQCJNOB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:134.604
Molecular Formula:C6H11ClO
InChIKey:MFIQXAVMTLKUJR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:211.086
Molecular Formula:C8H12Cl2O2
InChIKey:ZQFXOLLXFCTLHA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:460.6906
Molecular Formula:C32H44O2
InChIKey:WKPHSONARIQLJO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:134.604
Molecular Formula:C6H11ClO
InChIKey:SMUKODJVMQOSAB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:112.1696
Molecular Formula:C7H12O
InChIKey:XCNUTNIUANPMKW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:56.1063
Molecular Formula:C4H8
InChIKey:VXNZUUAINFGPBY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:193.07
Molecular Formula:C8H10Cl2O
InChIKey:CDVCMCKVKFZZAW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:82.1436
Molecular Formula:C6H10
InChIKey:NFJPEKRRHIYYES-UHFFFAOYSA-N
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Compound Information
Molecular Weight:195.086
Molecular Formula:C8H12Cl2O
InChIKey:OYRGBEQRFXNGQS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:126.1962
Molecular Formula:C8H14O
InChIKey:Not Available
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Compound Information
Molecular Weight:244.331
Molecular Formula:C4H3Cl5O
InChIKey:KRNCRUFKDXQLJZ-UHFFFAOYSA-N
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