Standard Article

The Pauson–Khand Cycloaddition Reaction for Synthesis of Cyclopentenones

  1. Neil E. Schore

Published Online: 15 OCT 2004

DOI: 10.1002/0471264180.or040.01

Organic Reactions

Organic Reactions

How to Cite

Schore, N. E. 2004. The Pauson–Khand Cycloaddition Reaction for Synthesis of Cyclopentenones. Organic Reactions. 40:1:1–90.

Author Information

  1. University of California, Department of Chemistry, Davis, California

Publication History

  1. Published Online: 15 OCT 2004

Chemistry Terms

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Abstract

The Pauson–Khand reaction is a cocycloaddition of alkynes, alkenes, and carbon monoxide to generate cyclopentenones in a formal [2 + 2 + 1] cycloaddition process. The reaction was discovered and first reported in detail by Ihsan U. Khand and Peter L. Pauson in 1973 in the course of a study aimed principally at the preparation and characterization of various alkene and alkyne complexes derived from Co2(CO)8. The generality of the reaction, typically carried out by heating a mixture of the alkene and the readily formed Co2(CO)6 complex of the alkyne in hydrocarbon or ethereal solvent, was established primarily by an extensive series of studies carried out by the Pauson group throughout the 1970s.

The earliest studies established that synthetically reasonable yields, usually in the 40–60% range, and significant regio- and stereoselectivity could be expected even for relatively simple examples. Development of this reaction has reached the point where predictable success and control of selectivity are possible. The variety of successful reactions and systems accessible by means of this cycloaddition is now quite substantial.

This chapter addresses the scope and generality of this reaction as well as the current state of the art with regard to control of regio- and stereochemistry. Both inter- and intramolecular versions of the cycloaddition are presented, and current models that have been put forth concerning the reaction mechanism are noted. Synthetic applications of the Pauson–Khand reaction have taken many forms, and representative examples of all major types of systems accessed are presented. The process exemplifies a nearly ideal merging of organometallic with synthetic chemistry, in which advances in each area have promoted development in the other in an almost symbiotic manner. Excellent shorter reviews on the Pauson–Khand reaction have been published. This chapter will provides the reader with both an overview of the reaction as well as a sufficiently detailed understanding of its complexities to permit meaningful evaluation as a possible solution to current or future research needs.

Keywords:

  • Pauson–Khand reaction;
  • cycloaddition;
  • intermolecular reaction;
  • cyclopentanones;
  • acyclic alkenes;
  • mechanism;
  • monocyclic alkenes;
  • ring fused bicyclics;
  • polycyclic alkenes;
  • bridged compounds;
  • intermolecular reaction;
  • all-carbon enynes;
  • heteroatom-linked alkenes;
  • synthesis applications;
  • experimental procedures;
  • ethylene;
  • scope;
  • enynes;
  • limitation

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  1. 1 - 250
Compound Information
Molecular Weight:0
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:192.2112
Molecular Formula:C11H12O3
InChIKey:SJIRIDSLOZMVJQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:126.1962
Molecular Formula:C8H14O
InChIKey:BYBSDCWTWYGDPM-VOTSOKGWSA-N
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Compound Information
Molecular Weight:116.1598
Molecular Formula:C9H8
InChIKey:GHUURDQYRGVEHX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:356.3353
Molecular Formula:C20H16CrO3
InChIKey:ZKXHPCTYMFIDSG-WPSKLUMWSA-N
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Compound Information
Molecular Weight:214.3459
Molecular Formula:C16H22
InChIKey:XAXBHLVDSGMZBE-AWGJLQHSSA-N
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Compound Information
Molecular Weight:236.3083
Molecular Formula:C17H16O
InChIKey:SFIQYOQIQVZENR-NXZHAISVSA-N
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Compound Information
Molecular Weight:274.621
Molecular Formula:C11H7ClCrO3
InChIKey:ZFBHXSZHQIZWGW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:278.345
Molecular Formula:C19H18O2
InChIKey:BPEHMJLYAZRGOU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:218.3159
Molecular Formula:C12H27OP
InChIKey:MNZAKDODWSQONA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:54.0904
Molecular Formula:C4H6
InChIKey:XSGHLZBESSREDT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:114.2285
Molecular Formula:C8H18
InChIKey:Not Available
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Molecular Weight:140.1366
Molecular Formula:C7H8O3
InChIKey:YNCKAQVPQJWLJW-UHFFFAOYSA-N
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Molecular Weight:226.312
Molecular Formula:C13H22O3
InChIKey:CQEJSFOLCCFONX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:113.2007
Molecular Formula:C7H15N
InChIKey:RWKDECTXBYSORQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:268.738
Molecular Formula:C17H13ClO
InChIKey:JQIYGARIRUAYEN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:168.3082
Molecular Formula:C9H16OSi
InChIKey:PEKCYYVUQIEQGG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:240.727
Molecular Formula:C16H13Cl
InChIKey:XLHSIACSHBDRSU-ZVSIBQGLSA-N
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Compound Information
Molecular Weight:122.1396
Molecular Formula:C8H7F
InChIKey:JWVTWJNGILGLAT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:234.2925
Molecular Formula:C17H14O
InChIKey:YHUCEEXFBYAMJY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:190.262
Molecular Formula:C11H10OS
InChIKey:KSADKRWZKSXYEE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:204.331
Molecular Formula:C13H16S
InChIKey:APYURLUIBYBGBT-FUZXSYEZSA-N
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Compound Information
Molecular Weight:172.2231
Molecular Formula:C12H12O
InChIKey:HYTOBZXFHCZOEC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:400.3448
Molecular Formula:C21H16CrO5
InChIKey:ZCLNGGSCKLPMDO-UHFFFAOYSA-N
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Molecular Weight:260.3282
Molecular Formula:C16H20O3
InChIKey:JOZQLQHQWNYYNL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:154.2063
Molecular Formula:C9H14O2
InChIKey:WWMSRZSZGZNEMT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:232.341
Molecular Formula:C14H16OS
InChIKey:YWHKPGVPWCMYRM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:268.738
Molecular Formula:C17H13ClO
InChIKey:NAUDDNVUEGOBAV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:384.3454
Molecular Formula:C21H16CrO4
InChIKey:JUORZOBXQCZHMV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:220.3089
Molecular Formula:C17H16
InChIKey:RLPHUWOYMLCVQW-RVPDKONISA-N
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Compound Information
Molecular Weight:138.594
Molecular Formula:C8H7Cl
InChIKey:KTZVZZJJVJQZHV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:270.4091
Molecular Formula:C19H26O
InChIKey:YACJRACEJMFJRY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:154.2063
Molecular Formula:C9H14O2
InChIKey:BKXMCMSBKYTEIA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:254.2021
Molecular Formula:C12H10CrO3
InChIKey:PBHXMDGHUCMCIU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:183.206
Molecular Formula:C12H9NO
InChIKey:SGOGNLSDFMLNOP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:150.2176
Molecular Formula:C10H14O
InChIKey:IVLCENBZDYVJPA-ONEGZZNKSA-N
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Compound Information
Molecular Weight:140.2658
Molecular Formula:C10H20
InChIKey:AFFLGGQVNFXPEV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:110.1968
Molecular Formula:C8H14
InChIKey:LDLDYFCCDKENPD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:232.3196
Molecular Formula:C18H16
InChIKey:BOBLSBAZCVBABY-WPWUJOAOSA-N
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Compound Information
Molecular Weight:404.764
Molecular Formula:C20H13ClCrO4
InChIKey:ZTCPYFBGDPVZEB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:94.1112
Molecular Formula:C6H6O
InChIKey:QQBUHYQVKJQAOB-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:254.2021
Molecular Formula:C12H10CrO3
InChIKey:VBBJECWYLBIXQC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:248.2744
Molecular Formula:C14H16O4
InChIKey:ANPNQJOMGQXDGY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:270.2015
Molecular Formula:C12H10CrO4
InChIKey:KZBCSVOJFVKIQB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:68.117
Molecular Formula:C5H8
InChIKey:NKTDTMONXHODTI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:183.206
Molecular Formula:C12H9NO
InChIKey:XNUZFMIXEJNOCG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:220.3089
Molecular Formula:C17H16
InChIKey:HWOHNKOFLQZHJO-NXZHAISVSA-N
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Compound Information
Molecular Weight:224.2546
Molecular Formula:C15H12O2
InChIKey:LLQZSIDZXIKODV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:370.3189
Molecular Formula:C20H14CrO4
InChIKey:HIFJEAGKOUHXSU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:232.341
Molecular Formula:C14H16OS
InChIKey:JGPYHRHYYXBHQM-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:220.287
Molecular Formula:C12H12O2S
InChIKey:URJPARLQAXWWSO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:254.2021
Molecular Formula:C12H10CrO3
InChIKey:DROHMQOVQUBZTB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:212.33
Molecular Formula:C16H20
InChIKey:CLFAFRQWODRFKD-FNCQTZNRSA-N
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Compound Information
Molecular Weight:99.1741
Molecular Formula:C6H13N
InChIKey:GKTJBVBQYZOQNJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:342.212
Molecular Formula:C21H18FeO
InChIKey:JJRLFGONPPUWLN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:138.2069
Molecular Formula:C9H14O
InChIKey:VEJCYYGKILCIFP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:242.356
Molecular Formula:C17H22O
InChIKey:GHARMEYTSNJOMM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:168.2328
Molecular Formula:C10H16O2
InChIKey:VYQSNYSJFCGYHK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:248.319
Molecular Formula:C18H16O
InChIKey:KARSGUXNBMPVLB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:229.3175
Molecular Formula:C15H19NO
InChIKey:VHQDIBMFHKCQFT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:260.3297
Molecular Formula:C19H16O
InChIKey:SPLHDIRDLPQTFB-VAWYXSNFSA-N
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Compound Information
Molecular Weight:150.2176
Molecular Formula:C10H14O
InChIKey:PUNQKBBBNHIIIX-ARJAWSKDSA-N
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Compound Information
Molecular Weight:212.352
Molecular Formula:C12H20OS
InChIKey:JSTUTEHUPUYFKH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:268.738
Molecular Formula:C17H13ClO
InChIKey:IDUOBVJGPMOVCA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:246.368
Molecular Formula:C15H18OS
InChIKey:UPLUQPGSJZYIHN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:192.2973
Molecular Formula:C13H20O
InChIKey:JOPHVTIQNMBDFK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:150.2606
Molecular Formula:C11H18
InChIKey:DLIZMWTUXLDHEH-YNRRLODASA-N
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Compound Information
Molecular Weight:142.1956
Molecular Formula:C8H14O2
InChIKey:NRAKYXXDEXCVMV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:226.312
Molecular Formula:C13H22O3
InChIKey:ACHPAHUVTRVJDD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:404.764
Molecular Formula:C20H13ClCrO4
InChIKey:ZAIPXPKBLLKEIV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:140.1366
Molecular Formula:C7H8O3
InChIKey:IAQZQUFZWSAUCE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:60.0843
Molecular Formula:O2Si
InChIKey:VYPSYNLAJGMNEJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:152.2334
Molecular Formula:C10H16O
InChIKey:XUMYZVPKJLICNW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:194.3132
Molecular Formula:C13H22O
InChIKey:TXUAGZAFNIOWJT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:243.344
Molecular Formula:C16H21NO
InChIKey:IPXHJPOCSUILBU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:296.383
Molecular Formula:C18H16O2S
InChIKey:YLKAQLLOKCPWNV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:110.1968
Molecular Formula:C8H14
InChIKey:YKCQGTKPNABNLF-VOTSOKGWSA-N
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Compound Information
Molecular Weight:116.224
Molecular Formula:C6H12S
InChIKey:VLMMKBGQSJLXIH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:258.166
Molecular Formula:C11H7CrFO3
InChIKey:IZLYDPPWHUYMFY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:54.0904
Molecular Formula:C4H6
InChIKey:XNMQEEKYCVKGBD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:116.1583
Molecular Formula:C6H12O2
InChIKey:XAYQGCCKMYHLLJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:212.352
Molecular Formula:C12H20OS
InChIKey:VVAVTDWAMOHGMF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:384.3454
Molecular Formula:C21H16CrO4
InChIKey:CRFDVXPQIONHKX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:106.949
Molecular Formula:C2H3Br
InChIKey:INLLPKCGLOXCIV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:150.2176
Molecular Formula:C10H14O
InChIKey:BHDFMGOSCXUMDG-ONEGZZNKSA-N
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Compound Information
Molecular Weight:254.3667
Molecular Formula:C18H22O
InChIKey:QZBIAZVHIHBIOY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:264.3184
Molecular Formula:C18H16O2
InChIKey:VAUBOEDQFVBDIF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:264.3184
Molecular Formula:C18H16O2
InChIKey:OSKWBLCDDNXCBM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:224.2546
Molecular Formula:C15H12O2
InChIKey:HCFWRAQLKZPPCU-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:254.3667
Molecular Formula:C18H22O
InChIKey:LNSDQBZPRKCTSL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:250.3349
Molecular Formula:C18H18O
InChIKey:VUHYBUWCJSUZPQ-ASVGJQBISA-N
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Compound Information
Molecular Weight:260.3282
Molecular Formula:C16H20O3
InChIKey:XBKDQMVLQPPIMZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:134.1751
Molecular Formula:C9H10O
InChIKey:UAJRSHJHFRVGMG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:198.2588
Molecular Formula:C11H18O3
InChIKey:WSORTJLOAFHTBE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:314.202
Molecular Formula:C20H18Fe
InChIKey:AUBUPYHVKDJRAM-JPOQIXDASA-N
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Compound Information
Molecular Weight:122.1644
Molecular Formula:C8H10O
InChIKey:UQKQRMXTLOLWNC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:122.1644
Molecular Formula:C8H10O
InChIKey:ZZKPAHYZVOZUMD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:224.2961
Molecular Formula:C13H20O3
InChIKey:KDHIOWQSFJTRQG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:376.754
Molecular Formula:C19H13ClCrO3
InChIKey:BJEVOINFBINBPC-SYJVDPRUSA-N
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Compound Information
Molecular Weight:224.2961
Molecular Formula:C13H20O3
InChIKey:VUMMULUQYDDSTK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:118.1757
Molecular Formula:C9H10
InChIKey:HJWLCRVIBGQPNF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:222.2802
Molecular Formula:C13H18O3
InChIKey:YEUQSYYJXXXZCH-RQOWECAXSA-N
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Compound Information
Molecular Weight:370.3189
Molecular Formula:C20H14CrO4
InChIKey:FOLKRRRHYZHSSZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:222.2802
Molecular Formula:C13H18O3
InChIKey:YLFBPSFAKVXKNX-RQOWECAXSA-N
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Compound Information
Molecular Weight:384.3454
Molecular Formula:C21H16CrO4
InChIKey:KMVRFOQSAHXTEJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:196.2429
Molecular Formula:C11H16O3
InChIKey:YMVXPGAZGIZLAJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:388.3093
Molecular Formula:C20H13CrFO4
InChIKey:RQJPPDJOWZVWGI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:222.3663
Molecular Formula:C15H26O
InChIKey:GIIZEMGLIOHVLB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:148.2017
Molecular Formula:C10H12O
InChIKey:Not Available
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Compound Information
Molecular Weight:224.2961
Molecular Formula:C13H20O3
InChIKey:DMPKZWGCCUQFEF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:240.3401
Molecular Formula:C17H20O
InChIKey:DJJMZDAWIUNBLS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:222.3663
Molecular Formula:C15H26O
InChIKey:JEZCPKIJSKGSBG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:240.1755
Molecular Formula:C11H8CrO3
InChIKey:ZVFGFFSBWYFTBN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:102.198
Molecular Formula:C5H10S
InChIKey:KTYYHDZDBJAYQT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:112.2126
Molecular Formula:C8H16
InChIKey:KWKAKUADMBZCLK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:130.2279
Molecular Formula:C8H18O
InChIKey:DURPTKYDGMDSBL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:268.738
Molecular Formula:C17H13ClO
InChIKey:QCLDIPHAJVJKDC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:278.345
Molecular Formula:C19H18O2
InChIKey:DHGFZTULNVGWEF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:124.1803
Molecular Formula:C8H12O
InChIKey:ZDWYQVBGIKBGDA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:242.356
Molecular Formula:C17H22O
InChIKey:MREZPAGJTQOZJA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:250.313
Molecular Formula:C13H14O3S
InChIKey:GDUIDRJCHFEWEM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:342.212
Molecular Formula:C21H18FeO
InChIKey:UXHBXXAFJRNNEV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:248.2744
Molecular Formula:C14H16O4
InChIKey:KCUDDRKXDCBNGW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:100.1589
Molecular Formula:C6H12O
InChIKey:PGYJSURPYAAOMM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:250.313
Molecular Formula:C13H14O3S
InChIKey:KFWASWOMMUKOSA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:218.358
Molecular Formula:C14H18S
InChIKey:AHWGZYYLVNIBLW-RCFWGOLESA-N
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Compound Information
Molecular Weight:215.3339
Molecular Formula:C15H21N
InChIKey:ZTVLUENXQNOXDL-KDYKCUIDSA-N
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Compound Information
Molecular Weight:194.25
Molecular Formula:C10H10O2S
InChIKey:HPKBNOKKLQPXCY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:168.3082
Molecular Formula:C9H16OSi
InChIKey:MWUSKPVDKKLREU-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:400.3448
Molecular Formula:C21H16CrO5
InChIKey:UTSDRTBBTSHMTE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:252.2829
Molecular Formula:C17H13FO
InChIKey:SJBDYNRSCMAFSG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:372.3347
Molecular Formula:C20H16CrO4
InChIKey:AWMFTRDKBPNYEF-VDHCIERPSA-N
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Compound Information
Molecular Weight:144.213
Molecular Formula:C11H12
InChIKey:BCRJHHFLBOQAMG-YNRRLODASA-N
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Compound Information
Molecular Weight:172.2231
Molecular Formula:C12H12O
InChIKey:KPIPKXAAUGXALH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:82.1436
Molecular Formula:C6H10
InChIKey:CGHIBGNXEGJPQZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:260.3297
Molecular Formula:C19H16O
InChIKey:MIFALJSCZSNGLZ-VAWYXSNFSA-N
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Compound Information
Molecular Weight:240.727
Molecular Formula:C16H13Cl
InChIKey:LASZRNUFCYQISX-KBXRYBNXSA-N
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Compound Information
Molecular Weight:164.2441
Molecular Formula:C11H16O
InChIKey:GVONPEQEUQYVNH-PLNGDYQASA-N
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Compound Information
Molecular Weight:112.245
Molecular Formula:C6H12Si
InChIKey:ULYLMHUHFUQKOE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:229.3175
Molecular Formula:C15H19NO
InChIKey:QXONJAKKLFFOBE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:152.2765
Molecular Formula:C11H20
InChIKey:GCDFTRNGRHQAJO-WJDMQLPWSA-N
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Compound Information
Molecular Weight:118.154
Molecular Formula:C4H6O2S
InChIKey:AFOSIXZFDONLBT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:196.2445
Molecular Formula:C14H12O
InChIKey:NEGLCKVMIYVNQX-LUZURFALSA-N
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Compound Information
Molecular Weight:270.4091
Molecular Formula:C19H26O
InChIKey:CNSCJDMHJKPKBF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:206.2824
Molecular Formula:C16H14
InChIKey:JFLKFZNIIQFQBS-FNCQTZNRSA-N
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Compound Information
Molecular Weight:164.2441
Molecular Formula:C11H16O
InChIKey:XMLSXPIVAXONDL-PLNGDYQASA-N
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Compound Information
Molecular Weight:218.2915
Molecular Formula:C14H18O2
InChIKey:FMKQATVGDGNUND-FUZXSYEZSA-N
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Compound Information
Molecular Weight:40.0639
Molecular Formula:C3H4
InChIKey:MWWATHDPGQKSAR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:256.3826
Molecular Formula:C18H24O
InChIKey:ACMDYOWGJDNJFE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:224.2961
Molecular Formula:C13H20O3
InChIKey:YAPOIOPWPMNNQP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:240.3401
Molecular Formula:C17H20O
InChIKey:QFEUIKMMXJJPRU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:246.368
Molecular Formula:C15H18OS
InChIKey:MMJQMZCBRSJYRU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:196.2429
Molecular Formula:C11H16O3
InChIKey:LAWHZMIVCGTTOY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:108.1809
Molecular Formula:C8H12
InChIKey:CLJGFLUQVGVHRX-ALCCZGGFSA-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:258.166
Molecular Formula:C11H7CrFO3
InChIKey:WOAVFQHRSKDVJF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:166.217
Molecular Formula:C10H14O2
InChIKey:QJCOQTJLNTYWGY-WAYWQWQTSA-N
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Compound Information
Molecular Weight:224.2728
Molecular Formula:C16H13F
InChIKey:LBZJODOUVVNCKN-KBXRYBNXSA-N
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Compound Information
Molecular Weight:112.1265
Molecular Formula:C6H8O2
InChIKey:NMQQBXHZBNUXGJ-SNAWJCMRSA-N
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Compound Information
Molecular Weight:248.319
Molecular Formula:C18H16O
InChIKey:MFUANGAPESLCQK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:94.1543
Molecular Formula:C7H10
InChIKey:NDBSYWQDUNOZGF-SREVYHEPSA-N
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Compound Information
Molecular Weight:342.3088
Molecular Formula:C19H14CrO3
InChIKey:PMPVAWVUWFAAOJ-XFJUYOQGSA-N
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Compound Information
Molecular Weight:101.9613
Molecular Formula:Al2O3
InChIKey:TWNQGVIAIRXVLR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:108.1378
Molecular Formula:C7H8O
InChIKey:FSKHBFWZOMLCDM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:194.3562
Molecular Formula:C14H26
InChIKey:IFIBQPBZFNQZGZ-PKBHSIMTSA-N
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Compound Information
Molecular Weight:150.2176
Molecular Formula:C10H14O
InChIKey:ZRPXEBBESHWNJZ-ARJAWSKDSA-N
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Compound Information
Molecular Weight:182.2594
Molecular Formula:C11H18O2
InChIKey:OXRDKMAZYOVCPY-WJPDYIDTSA-N
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Compound Information
Molecular Weight:208.3828
Molecular Formula:C15H28
InChIKey:MYRJWDWTCMMQNU-VVOKNZMXSA-N
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Compound Information
Molecular Weight:248.319
Molecular Formula:C18H16O
InChIKey:FXVLPRSYIIFTGI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:178.2292
Molecular Formula:C14H10
InChIKey:JRXXLCKWQFKACW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:168.2328
Molecular Formula:C10H16O2
InChIKey:XUVGNNBXORLBHE-HWKANZROSA-N
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Compound Information
Molecular Weight:256.3826
Molecular Formula:C18H24O
InChIKey:XFVGXEBOSQQKEZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:86.0892
Molecular Formula:C4H6O2
InChIKey:XTXRWKRVRITETP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:198.3019
Molecular Formula:C12H22O2
InChIKey:HPFUULDWQWVJHW-BLHCBFLLSA-N
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Compound Information
Molecular Weight:152.2334
Molecular Formula:C10H16O
InChIKey:ILHZVKAXFCDFMT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:212.069
Molecular Formula:C12H12Fe
InChIKey:VHFBWYOWUOEUBM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:252.2829
Molecular Formula:C17H13FO
InChIKey:GVMYRTIQWBFOSQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:190.262
Molecular Formula:C11H10OS
InChIKey:ICPWBZQTTNZFGD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:158.1965
Molecular Formula:C11H10O
InChIKey:UHTNKICWCQWOBM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:53.0626
Molecular Formula:C3H3N
InChIKey:NLHHRLWOUZZQLW-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:341.9472
Molecular Formula:C8Co2O8
InChIKey:NFWSABSVGZVHCA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:120.976
Molecular Formula:C3H5Br
InChIKey:BHELZAPQIKSEDF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:28.0101
Molecular Formula:CO
InChIKey:UGFAIRIUMAVXCW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:124.1803
Molecular Formula:C8H12O
InChIKey:TZJMINBYXYFIGT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:172.2231
Molecular Formula:C12H12O
InChIKey:KPIPKXAAUGXALH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:202.3165
Molecular Formula:C12H27P
InChIKey:TUQOTMZNTHZOKS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:242.399
Molecular Formula:C18H26
InChIKey:HFZFTFXFOCZADZ-MKQCFFQWSA-N
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Compound Information
Molecular Weight:356.3353
Molecular Formula:C20H16CrO3
InChIKey:TYHXFNJAKUGPMU-VDHCIERPSA-N
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Compound Information
Molecular Weight:270.2015
Molecular Formula:C12H10CrO4
InChIKey:BTVPYBRDEQYFBY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:94.1543
Molecular Formula:C7H10
InChIKey:WQJLVXFVPLIGBI-HWKANZROSA-N
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Compound Information
Molecular Weight:138.594
Molecular Formula:C8H7Cl
InChIKey:ISRGONDNXBCDBM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:130.1864
Molecular Formula:C10H10
InChIKey:XZKRXPZXQLARHH-XVNBXDOJSA-N
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Compound Information
Molecular Weight:110.1968
Molecular Formula:C8H14
InChIKey:QCQALVMFTWRCFI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:243.344
Molecular Formula:C16H21NO
InChIKey:PMUCNIFLMMIUIG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:360.2992
Molecular Formula:C19H13CrFO3
InChIKey:YOCXICXQBSWPNG-SYJVDPRUSA-N
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Compound Information
Molecular Weight:184.342
Molecular Formula:C11H20S
InChIKey:HUDBHQBXSAOWQH-BLHCBFLLSA-N
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Compound Information
Molecular Weight:108.1378
Molecular Formula:C7H8O
InChIKey:XCNKMUZHZUXPIS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:248.319
Molecular Formula:C18H16O
InChIKey:IZLNMXQJLOSFTG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:134.198
Molecular Formula:C8H6S
InChIKey:KTDJFTDAVHPTDO-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:166.26
Molecular Formula:C11H18O
InChIKey:YCIXWYOBMVNGTB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:158.1965
Molecular Formula:C11H10O
InChIKey:VHRGUJICHLPTDW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:156.2221
Molecular Formula:C9H16O2
InChIKey:QDOFUCCXJZBLCB-VNKDHWASSA-N
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Compound Information
Molecular Weight:172.2231
Molecular Formula:C12H12O
InChIKey:COKKKPKEKLIXHB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:198.2588
Molecular Formula:C11H18O3
InChIKey:AXVAUHHIWUOLNA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:166.26
Molecular Formula:C11H18O
InChIKey:NEZHCMOOOIHCJA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:388.3093
Molecular Formula:C20H13CrFO4
InChIKey:YBXYUCOPUQGHLE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:155.1959
Molecular Formula:C11H9N
InChIKey:JDCCCHBBXRQRGU-VDESZNBCSA-N
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Compound Information
Molecular Weight:104.1491
Molecular Formula:C8H8
InChIKey:PPBRXRYQALVLMV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:201.3074
Molecular Formula:C14H19N
InChIKey:JDLPAIZZSHAMGH-SWACZAGFSA-N
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Compound Information
Molecular Weight:84.1595
Molecular Formula:C6H12
InChIKey:PKXHXOTZMFCXSH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:234.2925
Molecular Formula:C17H14O
InChIKey:HTHQJAPXGRBADR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:26.0373
Molecular Formula:C2H2
InChIKey:HSFWRNGVRCDJHI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:192.2973
Molecular Formula:C13H20O
InChIKey:PFFIXJOAFBXHLL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:384.3454
Molecular Formula:C21H16CrO4
InChIKey:AYVIVUHGTSDYLX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:236.3929
Molecular Formula:C16H28O
InChIKey:HEWYOHFUUMRZJS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:138.2069
Molecular Formula:C9H14O
InChIKey:IJDOBJXZFNYSNG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:118.1757
Molecular Formula:C9H10
InChIKey:JLBJTVDPSNHSKJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:194.3132
Molecular Formula:C13H22O
InChIKey:NKYNHUACCNVEHH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:236.3929
Molecular Formula:C16H28O
InChIKey:YBNDBKQYABSMOR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:226.3135
Molecular Formula:C16H18O
InChIKey:KYUGEKVJFNTZBH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:56.0633
Molecular Formula:C3H4O
InChIKey:TVDSBUOJIPERQY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:130.1864
Molecular Formula:C10H10
InChIKey:Not Available
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Compound Information
Molecular Weight:94.1543
Molecular Formula:C7H10
InChIKey:LMULYBMQCQUKHQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:262.4625
Molecular Formula:C16H26OSi
InChIKey:YJAAABFBRQEMMT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:234.4094
Molecular Formula:C14H22OSi
InChIKey:XILYHHSAMKITBC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:232.3181
Molecular Formula:C15H20O2
InChIKey:NVHWTIFADTUUSO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:196.673
Molecular Formula:C11H13ClO
InChIKey:BNTIPLWTHSCFKU-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:209.3278
Molecular Formula:C13H23NO
InChIKey:NQTPTMWVXHKYDO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:118.154
Molecular Formula:C4H6O2S
InChIKey:MBDNRNMVTZADMQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:220.3089
Molecular Formula:C17H16
InChIKey:MCXUZXVIQZNGSA-SQIWNDBBSA-N
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Compound Information
Molecular Weight:184.2338
Molecular Formula:C13H12O
InChIKey:IUJFRTULAVELSH-UHFFFAOYSA-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:258.3569
Molecular Formula:C20H18
InChIKey:ZENGMMQJMCPHTK-FPPPDJHPSA-N
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Compound Information
Molecular Weight:230.3038
Molecular Formula:C18H14
InChIKey:BULLHRADHZGONG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:208.2536
Molecular Formula:C12H16O3
InChIKey:ZSKUANLLLAHJDU-IMDBTTTGSA-N
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Compound Information
Molecular Weight:178.2707
Molecular Formula:C12H18O
InChIKey:ANYIXRHGDAUBDW-DTHBNOIPSA-N
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Compound Information
Molecular Weight:234.4094
Molecular Formula:C14H22OSi
InChIKey:ZJFPHGWGDPEZNW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:260.2851
Molecular Formula:C15H16O4
InChIKey:FJRUHBRBPXVEIU-XOEAPDPESA-N
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Compound Information
Molecular Weight:168.1898
Molecular Formula:C9H12O3
InChIKey:TWQRQVWWYRDIDR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:202.2921
Molecular Formula:C14H18O
InChIKey:BCKHQHSGOAKSDW-ZJMQZLNVSA-N
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Compound Information
Molecular Weight:198.2604
Molecular Formula:C14H14O
InChIKey:AEYPWOJPYJAJMJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:134.1751
Molecular Formula:C9H10O
InChIKey:YMCXOGXGPAXVQN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:148.2017
Molecular Formula:C10H12O
InChIKey:LYRPISYGBPLNST-UHFFFAOYSA-N
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