Standard Article

The Vinylcyclopropane–Cyclopentene Rearrangement

  1. Tomáš Hudlický,
  2. Toni M. Kutchan,
  3. Saiyid M. Naqvi

Published Online: 15 OCT 2004

DOI: 10.1002/0471264180.or033.02

Organic Reactions

Organic Reactions

How to Cite

Hudlický, T., Kutchan, T. M. and Naqvi, S. M. 2004. The Vinylcyclopropane–Cyclopentene Rearrangement. Organic Reactions. 33:2:247–335.

Author Information

  1. Virginia Polytechnic Institute and State University, Department of Chemistry, Blacksburg, Virginia

  1. St. Louis University, Medical School, Department of Biochemistry, St. Louis, Missouri

  2. Illinois Institute of Technology, Department of Chemistry, Chicago, Illinois

Publication History

  1. Published Online: 15 OCT 2004

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Abstract

The vinylcyclopropane-cyclopentene isomerization was discovered in 1959. After the mechanism was studied in detail, this rearrangement was incorporated into many useful synthetic schemes. Various heterocyclic permutations of the vinylcyclopropane system have also been investigated, yielding several synthetic methods based on the rearrangements of cyclopropyl ketones and cyclopropyl imines to dihydrofurans and dihydropyrroles, respectively. This chapter is concerned only with the rearrangements of vinylcyclopropanes to cyclopentenes. Excluded are Cope rearrangements of divinylcyclopropanes and rearrangements of cyclopropyl compounds not leading to cyclopentenes.

The isomerization of 2,2-dichlorovinylcyclopropane was described in 1959. The rearrangement of the parent hydrocarbon was reported independently by two laboratories a year later. Although no prior mention of this rearrangement exists in the literature, it appears likely that it occured unobserved as early as 1922 during the preparation of vinylcyclopropane by drastic methods. The presence of cyclopentene in the reaction mixtures resulting from the Hofmann elimination of a β-cyclopropylethylammonium salt is a likely possibility, considering the low temperature at which vinylcyclopropane rearranges. The detection and identification of reaction products by refractive indices only may have prevented recognition of the isomerization at that time.

During the decade following the discovery of the rearrangement, virtually every simple vinylcyclopropane was studied in an attempt to settle the question of biradical versus concerted mechanism. Later there was intense activity in the applications of this rearrangement and many of its analogs to organic synthesis. Studies have also emphasized transition-metal-catalyzed rearrangements of vinylcyclopropanes.

Keywords:

  • vinylcyclopropane;
  • cyclopentene;
  • rearrangement;
  • mechanisms;
  • thermal rearrangements;
  • photochemical rearrangements;
  • transition metal catalysts;
  • scope;
  • limitations;
  • annulations;
  • natural products;
  • 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:144.213
Molecular Formula:C11H12
InChIKey:NURGUZSYYMQRPI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:276.3309
Molecular Formula:C15H20N2O3
InChIKey:VSOSWQSLIKLSQB-WJNAGGCUSA-N
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Compound Information
Molecular Weight:80.1277
Molecular Formula:C6H8
InChIKey:LWDUGATUDNIVEU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:168.2759
Molecular Formula:C11H20O
InChIKey:JTHVYOIHZNYRCC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:328.3145
Molecular Formula:C15H20O8
InChIKey:XWUUCPJJUDKCLC-AATRIKPKSA-N
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Compound Information
Molecular Weight:128.985
Molecular Formula:C3H6Cl2O
InChIKey:LUTWEKBTDWRTSE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:124.1803
Molecular Formula:C8H12O
InChIKey:HAUNPYVLVAIUOO-UHFFFAOYSA-N
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Molecular Weight:124.1803
Molecular Formula:C8H12O
InChIKey:ANHGJPVVVCMVOS-UHFFFAOYSA-N
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Molecular Weight:98.143
Molecular Formula:C6H10O
InChIKey:FHYLDABSPVPDTJ-UHFFFAOYSA-N
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Molecular Weight:94.1543
Molecular Formula:C7H10
InChIKey:UDKCHWVGPNQSQK-UHFFFAOYSA-N
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Molecular Weight:232.3196
Molecular Formula:C18H16
InChIKey:JZSPDNUNYOINOM-UHFFFAOYSA-N
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Molecular Weight:82.1436
Molecular Formula:C6H10
InChIKey:FWMRUAODTCVEQK-UHFFFAOYSA-N
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Molecular Weight:80.1277
Molecular Formula:C6H8
InChIKey:IVEZRSRZCUPBIF-UHFFFAOYSA-N
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Molecular Weight:144.213
Molecular Formula:C11H12
InChIKey:OPIZCXOIOINPNM-GXSJLCMTSA-N
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Molecular Weight:110.177
Molecular Formula:C6H6S
InChIKey:RMVRSNDYEFQCLF-UHFFFAOYSA-N
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Molecular Weight:154.2063
Molecular Formula:C9H14O2
InChIKey:GCWPTUQEFGYCEC-VOTSOKGWSA-N
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Molecular Weight:82.1436
Molecular Formula:C6H10
InChIKey:PRBHEGAFLDMLAL-XQRVVYSFSA-N
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Compound Information
Molecular Weight:234.4524
Molecular Formula:C15H26Si
InChIKey:KEOYOTQSDRSSST-SDNWHVSQSA-N
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Compound Information
Molecular Weight:164.2441
Molecular Formula:C11H16O
InChIKey:JUFBYDNAUULLOP-UHFFFAOYSA-N
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Molecular Weight:338.4816
Molecular Formula:C20H34O4
InChIKey:NOFOAYPPHIUXJR-APNQCZIXSA-N
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Molecular Weight:258.1197
Molecular Formula:C9H15O2Rh
InChIKey:FOKWBJHDUWSGAS-FGSKAQBVSA-M
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Molecular Weight:68.117
Molecular Formula:C5H8
InChIKey:YIWFBNMYFYINAD-UHFFFAOYSA-N
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Molecular Weight:168.2328
Molecular Formula:C10H16O2
InChIKey:PGOOIXANZJQLLV-BQYQJAHWSA-N
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Compound Information
Molecular Weight:114.1424
Molecular Formula:C6H10O2
InChIKey:Not Available
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Molecular Weight:118.1757
Molecular Formula:C9H10
InChIKey:ZMCCSKLGOXNRGF-XCADPSHZSA-N
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Compound Information
Molecular Weight:262.3441
Molecular Formula:C16H22O3
InChIKey:KHDUSKYCWZWYOG-CCZPAOOHSA-N
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Compound Information
Molecular Weight:152.1506
Molecular Formula:C7H8N2O2
InChIKey:ACORAKNHLIAFNQ-ONEGZZNKSA-N
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Compound Information
Molecular Weight:78.133
Molecular Formula:C2H6OS
InChIKey:IAZDPXIOMUYVGZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:209.0705
Molecular Formula:C8H10Rh
InChIKey:GVSYKWXMORHZRJ-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:222.0237
Molecular Formula:C6H7IO
InChIKey:MAKRQTKPKWXSRR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:266.3343
Molecular Formula:C18H18O2
InChIKey:ONKIUCGBPRSYFU-UHFFFAOYSA-N
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Molecular Weight:184.3507
Molecular Formula:C10H20OSi
InChIKey:HXBXHHNUZZPEHK-UHFFFAOYSA-N
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Molecular Weight:232.3196
Molecular Formula:C18H16
InChIKey:IKTGGBRWDDMDKB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:208.3721
Molecular Formula:C12H20OSi
InChIKey:LYIDFBFOYUESJE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:108.1809
Molecular Formula:C8H12
InChIKey:DYXZJKIAFPNJKH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:112.1265
Molecular Formula:C6H8O2
InChIKey:ZFDIRQKJPRINOQ-HWKANZROSA-N
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Compound Information
Molecular Weight:266.3758
Molecular Formula:C16H26O3
InChIKey:AMTSBTUGJRIHOK-OYNZBZHQSA-N
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Compound Information
Molecular Weight:168.2328
Molecular Formula:C10H16O2
InChIKey:BKBOZHPBLJGXHG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:184.1892
Molecular Formula:C9H12O4
InChIKey:FPWXTIVSNZCBAS-ONEGZZNKSA-N
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Compound Information
Molecular Weight:68.117
Molecular Formula:C5H8
InChIKey:Not Available
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Molecular Weight:110.1537
Molecular Formula:C7H10O
InChIKey:PSKWDFVNXXATCG-ZMONIFLSSA-N
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Compound Information
Molecular Weight:82.1436
Molecular Formula:C6H10
InChIKey:ATQUFXWBVZUTKO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:178.2707
Molecular Formula:C12H18O
InChIKey:JXIOQVHDPUGBJM-HVFQMFNGSA-N
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Compound Information
Molecular Weight:140.1797
Molecular Formula:C8H12O2
InChIKey:BLBGVYGAARHWAQ-UHFFFAOYSA-N
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Molecular Weight:156.2975
Molecular Formula:C8H16OSi
InChIKey:KVVRUOOPLTUXAP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:248.3175
Molecular Formula:C15H20O3
InChIKey:WABOKNQHUBNDOR-NZBLATKJSA-N
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Compound Information
Molecular Weight:82.1436
Molecular Formula:C6H10
InChIKey:SDJHPPZKZZWAKF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:286.475
Molecular Formula:C19H26S
InChIKey:VTPXMWYPWOYNCH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:294.389
Molecular Formula:C23H18
InChIKey:WQHLKQYIBYUTOW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:194.3886
Molecular Formula:C12H22Si
InChIKey:YCAWDHISWXKJIE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:84.1164
Molecular Formula:C5H8O
InChIKey:WEIMJSIRDZDHAH-UHFFFAOYSA-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:94.1543
Molecular Formula:C7H10
InChIKey:ISSYTHPTTMFJKL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:136.191
Molecular Formula:C9H12O
InChIKey:BUIRJJNQHZEOTJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:168.2328
Molecular Formula:C10H18O2
InChIKey:LMHABVLVTRACNA-GOJKSUSPSA-N
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Compound Information
Molecular Weight:80.1277
Molecular Formula:C6H8
InChIKey:YWQLRBQGXHZJCF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:137.007
Molecular Formula:C5H6Cl2
InChIKey:GAAAGAHNGGKSQH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:94.1543
Molecular Formula:C7H10
InChIKey:WBRNPACSUWTMKL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:112.1696
Molecular Formula:C7H12O
InChIKey:CGZZMOTZOONQIA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:136.234
Molecular Formula:C10H16
InChIKey:TWCNAXRPQBLSNO-NXEZZACHSA-N
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Compound Information
Molecular Weight:138.2069
Molecular Formula:C9H14O
InChIKey:BHUHVPPNIYZEKE-DTWKUNHWSA-N
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Compound Information
Molecular Weight:210.388
Molecular Formula:C12H22OSi
InChIKey:PTGSLCZUMAKICT-GDNZZTSVSA-N
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Compound Information
Molecular Weight:84.1164
Molecular Formula:C5H8O
InChIKey:BGTOWKSIORTVQH-UHFFFAOYSA-N
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Molecular Weight:150.2176
Molecular Formula:C10H14O
InChIKey:VZPIFEFIPUCWEE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:136.191
Molecular Formula:C9H12O
InChIKey:NTIRPGKCDYESKP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:200.3193
Molecular Formula:C15H20
InChIKey:LFJYBLJPNLTFSV-UHFFFAOYSA-N
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Molecular Weight:80.1277
Molecular Formula:C6H8
InChIKey:MTFFBUSJVZMBOK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:261.762
Molecular Formula:C10H14CuO4
InChIKey:QYJPSWYYEKYVEJ-FDGPNNRMSA-L
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Compound Information
Molecular Weight:82.1005
Molecular Formula:C5H6O
InChIKey:Not Available
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Molecular Weight:164.2044
Molecular Formula:C9H12N2O
InChIKey:CUKILKNVUNFTDQ-SNAWJCMRSA-N
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Molecular Weight:194.2271
Molecular Formula:C11H14O3
InChIKey:RAHRRVXEBILMFB-KOLCDFICSA-N
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Molecular Weight:146.2289
Molecular Formula:C11H14
InChIKey:KEJMCDIIYHPJOW-RWPVZYMPSA-N
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Compound Information
Molecular Weight:158.2396
Molecular Formula:C12H14
InChIKey:JFVQYLQTZQQPOP-OIXVIMQBSA-N
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Compound Information
Molecular Weight:286.475
Molecular Formula:C19H26S
InChIKey:GUZCAEJYTYNWFG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:378.6208
Molecular Formula:C22H38O3Si
InChIKey:VTHPFIYXYVOLJQ-LMQGHGSNSA-N
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Compound Information
Molecular Weight:82.1436
Molecular Formula:C6H10
InChIKey:JVVPJIPOOZHNTM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:124.1803
Molecular Formula:C8H12O
InChIKey:ITPSWFWOYFCDGH-HTQZYQBOSA-N
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Compound Information
Molecular Weight:86.0892
Molecular Formula:C4H6O2
InChIKey:BAPJBEWLBFYGME-UHFFFAOYSA-N
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Compound Information
Molecular Weight:138.2069
Molecular Formula:C9H14O
InChIKey:HKVNEAQDSNSEOI-BRPSZJMVSA-N
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Compound Information
Molecular Weight:234.4524
Molecular Formula:C15H26Si
InChIKey:DUJVUEHCCYJVQF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:232.3196
Molecular Formula:C18H16
InChIKey:MMTJRSFVCYLZDN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:150.1778
Molecular Formula:C8H10N2O
InChIKey:HUVVKMYVPPUYLP-ONEGZZNKSA-N
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Compound Information
Molecular Weight:204.308
Molecular Formula:C14H20O
InChIKey:HHQGSUCDFAGXDN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:152.631
Molecular Formula:C6H10CuLi
InChIKey:ZOGGDIUJYIBAQO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:234.377
Molecular Formula:C16H26O
InChIKey:KEHDVKZWULPKQR-SDNWHVSQSA-N
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Compound Information
Molecular Weight:388.757
Molecular Formula:C4Cl2O4Rh2
InChIKey:FGKDXBICTVUSPK-UHFFFAOYSA-L
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Compound Information
Molecular Weight:196.3614
Molecular Formula:C11H20OSi
InChIKey:ZOZQBIOQVMRHFJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:136.191
Molecular Formula:C9H12O
InChIKey:UXSWKQVGKDBMOX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:194.3132
Molecular Formula:C13H22O
InChIKey:KAPRXOJRIZOMFO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:208.3721
Molecular Formula:C12H20OSi
InChIKey:MUYYXPQDZKMLRS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:80.1277
Molecular Formula:C6H8
InChIKey:ZBNBSZJUIQGIHK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:70.0898
Molecular Formula:C4H6O
InChIKey:FUSUHKVFWTUUBE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:108.1809
Molecular Formula:C8H12
InChIKey:BBLGCIHIXUVYFY-DAXSKMNVSA-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:232.3214
Molecular Formula:C14H20N2O
InChIKey:TWDMZLGBONFNNJ-GQCTYLIASA-N
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Compound Information
Molecular Weight:232.3196
Molecular Formula:C18H16
InChIKey:SEVFHPVKEMBOCO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:156.174
Molecular Formula:C9H9LiS
InChIKey:GHIGKAVOSCBWNO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:122.2075
Molecular Formula:C9H14
InChIKey:HNXYQJYBEOPJOC-PQZOIKATSA-N
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Compound Information
Molecular Weight:110.1537
Molecular Formula:C7H10O
InChIKey:UZLQSPYGTUMKGS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:200.3193
Molecular Formula:C15H20
InChIKey:TWQLRNADHLZVDO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:84.1164
Molecular Formula:C5H8O
InChIKey:CZVVRZRQISXRAB-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:69.1232
Molecular Formula:C5H8
InChIKey:Not Available
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Compound Information
Molecular Weight:124.1803
Molecular Formula:C8H12O
InChIKey:BZWUSACBFYCVTN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:136.234
Molecular Formula:C10H16
InChIKey:IBVJWOMJGCHRRW-DTWKUNHWSA-N
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Compound Information
Molecular Weight:102.905
Molecular Formula:Rh
InChIKey:OBDSITLACDGNMC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:110.1537
Molecular Formula:C7H10O
InChIKey:XSOSLVVAKBKYRV-LURJTMIESA-N
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Compound Information
Molecular Weight:21.976
Molecular Formula:CH3Li
InChIKey:Not Available
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Compound Information
Molecular Weight:98.143
Molecular Formula:C6H10O
InChIKey:GKIATJNLLNNGJV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:204.308
Molecular Formula:C14H20O
InChIKey:RTLYWDYEFAYBCU-JTNHKYCSSA-N
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Compound Information
Molecular Weight:208.0626
Molecular Formula:C8H9Rh
InChIKey:BHNKCIOSHVRXOS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:80.1277
Molecular Formula:C6H8
InChIKey:NFWSQSCIDYBUOU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:184.1892
Molecular Formula:C9H12O4
InChIKey:CRTKZGLKBFSASC-NKWVEPMBSA-N
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Compound Information
Molecular Weight:200.364
Molecular Formula:C10H16S2
InChIKey:ZFIFMQQVSDZNID-UHFFFAOYSA-N
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Compound Information
Molecular Weight:175.023
Molecular Formula:C6H7BrO
InChIKey:BVSMYYHGYVHWCD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:106.165
Molecular Formula:C8H10
InChIKey:CJTXNSXMYCBHQB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:94.1543
Molecular Formula:C7H10
InChIKey:XOSQFCUFISUYLS-ARJAWSKDSA-N
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Compound Information
Molecular Weight:210.388
Molecular Formula:C12H22OSi
InChIKey:FYIGABCEGUPGSJ-NWDGAFQWSA-N
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Compound Information
Molecular Weight:128.212
Molecular Formula:C8H16O
InChIKey:ZPVFWPFBNIEHGJ-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:122.2075
Molecular Formula:C9H14
InChIKey:DFBZILPYKSEQDY-HYXAFXHYSA-N
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Compound Information
Molecular Weight:124.1803
Molecular Formula:C8H12O
InChIKey:Not Available
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Compound Information
Molecular Weight:80.1277
Molecular Formula:C6H8
InChIKey:Not Available
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Compound Information
Molecular Weight:172.311
Molecular Formula:C8H12S2
InChIKey:JFFNLDMFGAJVTG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:267.8355
Molecular Formula:CH2I2
InChIKey:NZZFYRREKKOMAT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:96.1702
Molecular Formula:C7H12
InChIKey:KBBOLTBWRZESTH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:188.2655
Molecular Formula:C13H16O
InChIKey:AVGYZMXDPQJTCJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:202.3352
Molecular Formula:C15H22
InChIKey:KEVTZKPBXQTBSV-UHFFFAOYSA-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:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:172.311
Molecular Formula:C8H12S2
InChIKey:XGWRRKVCCPMFPE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:138.2069
Molecular Formula:C9H14O
InChIKey:HAMUKWWZXAKCAU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:142.271
Molecular Formula:C7H14OSi
InChIKey:JOAPBVRQZQYKMS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:124.1803
Molecular Formula:C8H12O
InChIKey:NZTVVUIIJPWANB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:378.6208
Molecular Formula:C22H38O3Si
InChIKey:TZOVAHAOMKJBQW-ATVISUAKSA-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:204.3511
Molecular Formula:C15H24
InChIKey:VBZRHXLPRWBPEH-OXRVDDMESA-N
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Compound Information
Molecular Weight:154.2493
Molecular Formula:C10H18O
InChIKey:YKFKEYKJGVSEIX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:108.1809
Molecular Formula:C8H12
InChIKey:BCSKKKCQWNGMIV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:200.364
Molecular Formula:C10H16S2
InChIKey:FYWKJEVHLVAHBT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:200.3193
Molecular Formula:C15H20
InChIKey:PLFTUSXANQWOGX-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:160.234
Molecular Formula:C7H12O2S
InChIKey:SYJIAOOAJKIWNZ-SNAWJCMRSA-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:194.2271
Molecular Formula:C11H14O3
InChIKey:IDVRGSJRWPVYIY-AATRIKPKSA-N
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Compound Information
Molecular Weight:150.2176
Molecular Formula:C10H14O
InChIKey:QQIOVZCSUDXYPA-VQHVLOKHSA-N
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Compound Information
Molecular Weight:137.007
Molecular Formula:C5H6Cl2
InChIKey:GVZSEVSNGREDBC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:148.2017
Molecular Formula:C10H12O
InChIKey:NOXKUHSBIXPZBJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:128.955
Molecular Formula:CuZn
InChIKey:TVZPLCNGKSPOJA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:152.2334
Molecular Formula:C10H16O
InChIKey:KOHZFTUBIQKPNF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:204.3511
Molecular Formula:C15H24
InChIKey:Not Available
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Compound Information
Molecular Weight:136.191
Molecular Formula:C9H12O
InChIKey:BZUDJXIQAPEUDV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:124.1372
Molecular Formula:C7H8O2
InChIKey:XYRFGFRTVXZAIU-WDSKDSINSA-N
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Compound Information
Molecular Weight:234.377
Molecular Formula:C16H26O
InChIKey:JCIKTYSYQAMXJJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:120.236
Molecular Formula:C4H8S2
InChIKey:WQADWIOXOXRPLN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:32.0419
Molecular Formula:CH4O
InChIKey:OKKJLVBELUTLKV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:150.2176
Molecular Formula:C10H14O
InChIKey:OPTFVSHBGNEZEP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:226.2705
Molecular Formula:C15H14O2
InChIKey:SNRLVRBZACMUHU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:146.2289
Molecular Formula:C11H14
InChIKey:WZNHNAUGNUXVCX-ZJUUUORDSA-N
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Compound Information
Molecular Weight:166.8743
Molecular Formula:C8H12Ni
InChIKey:OHLZVWFESFOWTL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:80.1277
Molecular Formula:C6H8
InChIKey:XBDUWBOCEFNGGU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:122.1644
Molecular Formula:C8H10O
InChIKey:BTDXLOZJMXSYRM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:196.3614
Molecular Formula:C11H20OSi
InChIKey:PSRLQMVPYNSKQS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:239.936
Molecular Formula:C6H8Br2
InChIKey:PMZBTQHSPQUSAV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:172.311
Molecular Formula:C8H12S2
InChIKey:BRNFGFMXNVVSKK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:164.2441
Molecular Formula:C11H16O
InChIKey:CSJAIUYJNMOUDL-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:226.337
Molecular Formula:C15H14S
InChIKey:YXCIOUFSRRFVDB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:200.364
Molecular Formula:C10H16S2
InChIKey:FYWZDWZOLFZOIX-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:168.2328
Molecular Formula:C10H16O2
InChIKey:UXRAAZNTTGRBGN-MKSVKPQVSA-N
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Compound Information
Molecular Weight:290.3575
Molecular Formula:C16H22N2O3
InChIKey:LJQFCQKDRXTXLJ-DJYHAJFQSA-N
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Compound Information
Molecular Weight:92.524
Molecular Formula:C3H5ClO
InChIKey:XTIGGAHUZJWQMD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:112.1696
Molecular Formula:C7H12O
InChIKey:MKLARKDYEBNZFK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:118.1757
Molecular Formula:C9H10
InChIKey:ZASATNXXFMERCZ-RKDXNWHRSA-N
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Compound Information
Molecular Weight:1155.56
Molecular Formula:C72H60P4Pd
InChIKey:NFHFRUOZVGFOOS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:108.1809
Molecular Formula:C8H12
InChIKey:RXCSODBXHNSSCQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:122.1644
Molecular Formula:C8H10O
InChIKey:IHEHQTSUDJRWCQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:158.2396
Molecular Formula:C12H14
InChIKey:UXYOUHKSBUXYKR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:98.143
Molecular Formula:C6H10O
InChIKey:KTHYNBDPCSXGSI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:249.685
Molecular Formula:CuH10O9S
InChIKey:Not Available
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Compound Information
Molecular Weight:124.1803
Molecular Formula:C8H12O
InChIKey:OBDPTOBECPVDMB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:150.2176
Molecular Formula:C10H14O
InChIKey:HFGJGLXNMSXRIG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:294.389
Molecular Formula:C23H18
InChIKey:YMXDJWYBTXXWBM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:139.2525
Molecular Formula:C10H16
InChIKey:Not Available
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Compound Information
Molecular Weight:96.1702
Molecular Formula:C7H12
InChIKey:FONFXXNTLGAHGI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:141.2684
Molecular Formula:C10H18
InChIKey:Not Available
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Compound Information
Molecular Weight:238.2366
Molecular Formula:C12H14O5
InChIKey:QUKBVEXAKLFOLN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:122.1644
Molecular Formula:C8H10O
InChIKey:HMMDXMOYKXSSQU-BQBZGAKWSA-N
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Compound Information
Molecular Weight:122.1644
Molecular Formula:C8H10O
InChIKey:IJGPTRGYEZQWQS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:142.271
Molecular Formula:C7H14OSi
InChIKey:OOCMVRXBUSLCRM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:98.143
Molecular Formula:C6H10O
InChIKey:KEXJDRIDGBUTMG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:170.3241
Molecular Formula:C9H18OSi
InChIKey:OWMYMBVOOLHDET-VQHVLOKHSA-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:136.191
Molecular Formula:C9H12O
InChIKey:HCDXUEHTYDACME-UHFFFAOYSA-N
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Compound Information
Molecular Weight:80.1277
Molecular Formula:C6H8
InChIKey:Not Available
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Compound Information
Molecular Weight:98.143
Molecular Formula:C6H10O
InChIKey:GHHGVSCQWPVENX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:184.2322
Molecular Formula:C10H16O3
InChIKey:IZCWKOFOIDAIMK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:136.191
Molecular Formula:C9H12O
InChIKey:OXFXQPYSYRINER-UHFFFAOYSA-N
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Compound Information
Molecular Weight:140.1797
Molecular Formula:C8H12O2
InChIKey:VAXNALQNFKJVAU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:194.3886
Molecular Formula:C12H22Si
InChIKey:PZFXGMASXHWYTN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:82.1005
Molecular Formula:C5H6O
InChIKey:Not Available
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Compound Information
Molecular Weight:69.1232
Molecular Formula:C5H8
InChIKey:Not Available
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Compound Information
Molecular Weight:69.1232
Molecular Formula:C5H8
InChIKey:Not Available
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Compound Information
Molecular Weight:69.1232
Molecular Formula:C5H8
InChIKey:Not Available
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Compound Information
Molecular Weight:69.1232
Molecular Formula:C5H8
InChIKey:Not Available
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Compound Information
Molecular Weight:69.1232
Molecular Formula:C5H8
InChIKey:Not Available
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Compound Information
Molecular Weight:139.2525
Molecular Formula:C10H16
InChIKey:Not Available
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Compound Information
Molecular Weight:139.2525
Molecular Formula:C10H16
InChIKey:Not Available
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Compound Information
Molecular Weight:158.2396
Molecular Formula:C12H14
InChIKey:JFVQYLQTZQQPOP-SWGQDTFXSA-N
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Compound Information
Molecular Weight:168.2328
Molecular Formula:C10H16O2
InChIKey:UXRAAZNTTGRBGN-RWBYNWAKSA-N
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Compound Information
Molecular Weight:164.2441
Molecular Formula:C11H16O
InChIKey:VFJKRODSDNVBHG-KWQFWETISA-N
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Compound Information
Molecular Weight:118.1757
Molecular Formula:C9H10
InChIKey:ZASATNXXFMERCZ-BDAKNGLRSA-N
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Compound Information
Molecular Weight:146.2289
Molecular Formula:C11H14
InChIKey:WZNHNAUGNUXVCX-NXEZZACHSA-N
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Compound Information
Molecular Weight:108.1809
Molecular Formula:C8H12
InChIKey:BBLGCIHIXUVYFY-QPJJXVBHSA-N
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Compound Information
Molecular Weight:194.2271
Molecular Formula:C11H14O3
InChIKey:RAHRRVXEBILMFB-MWLCHTKSSA-N
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Compound Information
Molecular Weight:144.213
Molecular Formula:C11H12
InChIKey:OPIZCXOIOINPNM-MWLCHTKSSA-N
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Compound Information
Molecular Weight:108.1809
Molecular Formula:C8H12
InChIKey:BBLGCIHIXUVYFY-DAXSKMNVSA-N
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Compound Information
Molecular Weight:184.1892
Molecular Formula:C9H12O4
InChIKey:CRTKZGLKBFSASC-RNFRBKRXSA-N
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Compound Information
Molecular Weight:102.9055
Molecular Formula:Rh
InChIKey:MHOVAHRLVXNVSD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:80.1277
Molecular Formula:C6H8
InChIKey:ATQUFXWBVZUTKO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:110.1537
Molecular Formula:C7H10O
InChIKey:JQSSIIPMEVASOF-RRKCRQDMSA-N
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Compound Information
Molecular Weight:184.1892
Molecular Formula:C9H12O4
InChIKey:BTHUKAQVHWDTAH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:107.1531
Molecular Formula:C7H9N
InChIKey:CPROOEGTSQBHDQ-RQJHMYQMSA-N
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Compound Information
Molecular Weight:163.044
Molecular Formula:C7H8Cl2
InChIKey:PZXQVKQPZVCXHQ-OLQVQODUSA-N
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Compound Information
Molecular Weight:275.968
Molecular Formula:C9H8Br2
InChIKey:MLZKLKSSTQZXIC-XCADPSHZSA-N
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Compound Information
Molecular Weight:96.1702
Molecular Formula:C7H12
InChIKey:LNAVSCYUHFMDNS-FWDZIHJBSA-N
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Compound Information
Molecular Weight:166.1772
Molecular Formula:C8H10N2O2
InChIKey:ZPPJXZDRULODEO-MQQKCMAXSA-N
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Compound Information
Molecular Weight:151.034
Molecular Formula:C6H8Cl2
InChIKey:SPSFOLKETVFCTP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:156.2221
Molecular Formula:C9H16O2
InChIKey:HDCPOYMRKNZICF-BQYQJAHWSA-N
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Compound Information
Molecular Weight:98.1789
Molecular Formula:C7H10
InChIKey:Not Available
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Compound Information
Molecular Weight:106.165
Molecular Formula:C8H10
InChIKey:ZRFAFEJNCKPMCE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:96.1702
Molecular Formula:C7H12
InChIKey:PQMFTBQGLFFXOQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:122.2075
Molecular Formula:C9H14
InChIKey:CJKYISGZRPUIBG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:82.1436
Molecular Formula:C6H10
InChIKey:IVEZRSRZCUPBIF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:80.1277
Molecular Formula:C6H8
InChIKey:YWDBHFZUBPOPRQ-OLQVQODUSA-N
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Compound Information
Molecular Weight:136.191
Molecular Formula:C9H12O
InChIKey:NREINIKOQZTJNA-SUQDCXIYSA-N
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Compound Information
Molecular Weight:110.1537
Molecular Formula:C7H10O
InChIKey:XHRNQDMNINGCES-UHFFFAOYSA-N
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Compound Information
Molecular Weight:107.1531
Molecular Formula:C7H9N
InChIKey:PYQVZXKIZAECMT-WUCZRCLBSA-N
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Compound Information
Molecular Weight:110.1537
Molecular Formula:C7H10O
InChIKey:PJZNWOZWRMDBHQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:96.1271
Molecular Formula:C6H8O
InChIKey:RMCWOSMNBMMDPL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:70.1293
Molecular Formula:C5H8
InChIKey:Not Available
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Compound Information
Molecular Weight:116.589
Molecular Formula:C6H9Cl
InChIKey:IZZVBYCKDVTPGU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:120.1916
Molecular Formula:C9H12
InChIKey:PVXMNXKZWYCDMZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:124.1803
Molecular Formula:C8H12O
InChIKey:XGOFCBNEZVLFLK-ONEGZZNKSA-N
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Compound Information
Molecular Weight:298.15
Molecular Formula:C12H10MoO3
InChIKey:ZNSRWRULTFGRBD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:124.2127
Molecular Formula:C9H10
InChIKey:Not Available
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