Standard Article

Long-Lived Cyclopropylcarbinyl Cations

Cyclopropyl Group (1995)

  1. George A. Olah,
  2. Prakash V. Reddy,
  3. G. K. Surya Prakash

Published Online: 15 DEC 2009

DOI: 10.1002/9780470682531.pat0040

Patai's Chemistry of Functional Groups

Patai's Chemistry of Functional Groups

How to Cite

Olah, G. A., Reddy, P. V. and Surya Prakash, G. K. 2009. Long-Lived Cyclopropylcarbinyl Cations. Patai's Chemistry of Functional Groups. .

Author Information

  1. University of Southern California, Loker Hydrocarbon Research Institute and Department of Chemistry, Los Angeles, CA, USA

Publication History

  1. Published Online: 15 DEC 2009

Abstract

  • 1
    Introduction
  • 2
    General Methods of Preparation of Long-Lived Cyclopropylcarbinyl Cations
  • 3
    Primary Cyclopropylcarbinyl Cations
  • 4
    Secondary and Tertiary Cyclopropylcarbinyl Cations
  • 5
    Spirocyclopropylcarbinyl Cations
  • 6
    Cyclopropylcarbinyl Dications
  • 7
    Extent of Positive Charge Delocalization into the Cyclopropyl Group
  • 8
    X-Ray Crystallographic Studies
  • 9
    Conclusions and Outlook

Keywords:

  • long-lived cyclopropylcarbinyl cations;
  • primary cyclopropylcarbinyl cations;
  • alcohol or halide ionization;
  • hydride ion abstraction from hydrocarbons;
  • secondary and tertiary cyclopropylcarbinyl cations;
  • allyl substituted cyclopropylcarbinyl cations

Featured Compounds

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  1. 1 - 93
Compound 16
Molecular Weight:135.2256
Molecular Formula:C10H15
InChIKey:CBILMSIZAIZYPO-UHFFFAOYSA-N
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Compound 4a
Molecular Weight:194.701
Molecular Formula:C12H15Cl
InChIKey:JHYBDWSTSJYQIS-UHFFFAOYSA-M
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Compound 17
Molecular Weight:70.1329
Molecular Formula:C5H10
InChIKey:FOTXAJDDGPYIFU-UHFFFAOYSA-N
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Compound 18
Molecular Weight:70.1329
Molecular Formula:C5H10
InChIKey:FOTXAJDDGPYIFU-UHFFFAOYSA-N
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Compound 20
Molecular Weight:83.151
Molecular Formula:C6H11
InChIKey:GPTFPTIFCIXLBQ-UHFFFAOYSA-N
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Compound 20a
Molecular Weight:97.1776
Molecular Formula:C7H13
InChIKey:ZNFZCSKROWTMPS-UHFFFAOYSA-N
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Compound 5a
Molecular Weight:75.1242
Molecular Formula:C4H8O
InChIKey:Not Available
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Compound 5b
Molecular Weight:75.1242
Molecular Formula:C4H8O
InChIKey:Not Available
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Compound 8
Molecular Weight:69.1244
Molecular Formula:C5H9
InChIKey:GFHWZRRJTCLQPE-UHFFFAOYSA-N
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Compound 10
Molecular Weight:72.1429
Molecular Formula:C5H9
InChIKey:Not Available
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Compound 12
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 13
Molecular Weight:67.1085
Molecular Formula:C5H8
InChIKey:RUEUVIBOEYSPRK-UHFFFAOYSA-N
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Compound 15
Molecular Weight:107.1724
Molecular Formula:C8H12
InChIKey:ADEATTONFWKXIV-UHFFFAOYSA-N
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Compound 19
Molecular Weight:68.117
Molecular Formula:C5H8
InChIKey:OGNAOIGAPPSUMG-UHFFFAOYSA-N
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Compound 21
Molecular Weight:109.1883
Molecular Formula:C8H13
InChIKey:HYGAWEMKWDDZSO-UHFFFAOYSA-N
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Compound 22
Molecular Weight:123.2149
Molecular Formula:C9H15
InChIKey:IAXSZQJCCAOVKV-UHFFFAOYSA-N
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Compound 23
Molecular Weight:95.1617
Molecular Formula:C7H11
InChIKey:GRCAPIWAMJNJGD-UHFFFAOYSA-N
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Compound 25
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 26
Molecular Weight:161.2628
Molecular Formula:C12H17
InChIKey:JKZPPDAZSUDZDI-UHFFFAOYSA-N
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Compound 26a
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 27
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 28
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 29
Molecular Weight:119.1831
Molecular Formula:C9H12
InChIKey:LSYNYLMPUOTZGT-UHFFFAOYSA-N
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Compound 30a
Molecular Weight:121.199
Molecular Formula:C9H14
InChIKey:VWPSVEABOJTRRL-UHFFFAOYSA-N
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Compound 30b
Molecular Weight:121.199
Molecular Formula:C9H14
InChIKey:VWPSVEABOJTRRL-UHFFFAOYSA-N
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Compound 31
Molecular Weight:135.2256
Molecular Formula:C10H15
InChIKey:AMIOEGRKHFOAFF-UHFFFAOYSA-N
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Compound 32a
Molecular Weight:131.1938
Molecular Formula:C10H11
InChIKey:OBAXXKFJLUHFAD-UHFFFAOYSA-N
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Compound 32b
Molecular Weight:145.2204
Molecular Formula:C11H13
InChIKey:AVGILSALGGVWEY-UHFFFAOYSA-N
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Compound 32c
Molecular Weight:301.183
Molecular Formula:C19H17Fe
InChIKey:GKVQWTLTXLMLKX-UHFFFAOYSA-N
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Compound 33
Molecular Weight:221.2733
Molecular Formula:C16H13O
InChIKey:CFALYXWZKWHIML-UHFFFAOYSA-N
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Compound 34
Molecular Weight:144.2119
Molecular Formula:C11H12
InChIKey:GKQWLCHCIUWJJJ-UHFFFAOYSA-N
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Compound 35
Molecular Weight:145.2204
Molecular Formula:C11H13
InChIKey:HQQXFPFBJXVLLD-UHFFFAOYSA-N
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Compound 36
Molecular Weight:171.2577
Molecular Formula:C13H15
InChIKey:NWEDWYUGLZKKQP-UHFFFAOYSA-N
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Compound 37
Molecular Weight:93.1458
Molecular Formula:C7H9
InChIKey:CWIMJCBJRMDAKC-UHFFFAOYSA-N
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Compound 38
Molecular Weight:107.1724
Molecular Formula:C8H11
InChIKey:FUWXEIQRNMPSMS-UHFFFAOYSA-N
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Compound 39
Molecular Weight:107.1724
Molecular Formula:C8H11
InChIKey:SCVJSGRPHVFROA-UHFFFAOYSA-N
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Compound 40
Molecular Weight:93.1458
Molecular Formula:C7H9
InChIKey:OCVLNVYQHHHSQL-NSCUHMNNSA-N
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Compound 41
Molecular Weight:330.91
Molecular Formula:C7H11F6Sb
InChIKey:OBIACTAQVNKDQW-UHFFFAOYSA-H
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Compound 43
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 48
Molecular Weight:83.151
Molecular Formula:C6H12
InChIKey:DVMGLDYFDGLDOV-UHFFFAOYSA-N
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Compound 51
Molecular Weight:97.1776
Molecular Formula:C7H14
InChIKey:FQTAUSYPBCULMU-UHFFFAOYSA-N
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Compound 53
Molecular Weight:97.1776
Molecular Formula:C7H14
InChIKey:IJCCTFUEIJJAFV-UHFFFAOYSA-N
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Compound 54
Molecular Weight:97.1776
Molecular Formula:C7H14
InChIKey:BROHACKPLOJVQT-UHFFFAOYSA-N
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Compound 55
Molecular Weight:84.1595
Molecular Formula:C6H12
InChIKey:SAHWBARCQUAFSM-UHFFFAOYSA-N
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Compound 56
Molecular Weight:229.3799
Molecular Formula:C17H25
InChIKey:YUZWILNZVXKLCA-UHFFFAOYSA-N
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Compound 57
Molecular Weight:98.143
Molecular Formula:C6H10O
InChIKey:DXESCHCZVDAYPL-UHFFFAOYSA-N
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Compound 59
Molecular Weight:81.1351
Molecular Formula:C6H9
InChIKey:VCPBDSYFLCZBQP-UHFFFAOYSA-N
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Compound 58
Molecular Weight:112.1696
Molecular Formula:C7H12O
InChIKey:YUZVFUMVDCKMOI-UHFFFAOYSA-N
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Compound 63
Molecular Weight:95.1617
Molecular Formula:C7H11
InChIKey:WCODBHYTHVWBPB-UHFFFAOYSA-N
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Compound 67
Molecular Weight:110.1968
Molecular Formula:C8H14
InChIKey:AKHMHYGTZRJYBS-UHFFFAOYSA-N
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Compound 68
Molecular Weight:124.2233
Molecular Formula:C9H16
InChIKey:FYECUAIUGWFPJF-UHFFFAOYSA-N
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Compound 69
Molecular Weight:109.1883
Molecular Formula:C8H13
InChIKey:YTOOOWFXJYHTTR-UHFFFAOYSA-N
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Compound 70
Molecular Weight:107.1724
Molecular Formula:C8H12
InChIKey:XSLNQPCWDRPLBZ-UHFFFAOYSA-N
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Compound 74
Molecular Weight:134.2182
Molecular Formula:C10H14
InChIKey:OPFJNDIKPJNLNK-UHFFFAOYSA-N
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Compound 75
Molecular Weight:133.2097
Molecular Formula:C10H14
InChIKey:HMBSCWSUFYDANS-UHFFFAOYSA-N
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Compound 77
Molecular Weight:161.2628
Molecular Formula:C12H17
InChIKey:AUEZEBLUFYDOBC-UHFFFAOYSA-N
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Compound 78
Molecular Weight:210.3141
Molecular Formula:C16H18
InChIKey:JNGLPTRDJPRPPF-UHFFFAOYSA-N
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Compound 80
Molecular Weight:147.2363
Molecular Formula:C11H15
InChIKey:MOTSPNXJPOLDTF-UHFFFAOYSA-N
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Compound 82
Molecular Weight:147.2363
Molecular Formula:C11H16
InChIKey:UIZUGFRACBYMPM-UHFFFAOYSA-N
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Compound 83a
Molecular Weight:118.1757
Molecular Formula:C9H10
InChIKey:RHNDWILNXCGXLR-UHFFFAOYSA-N
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Compound 87
Molecular Weight:320.2973
Molecular Formula:C15H16N2O6
InChIKey:NWEXNXUPQJRBCB-UHFFFAOYSA-N
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Compound 88
Molecular Weight:322.3132
Molecular Formula:C15H18N2O6
InChIKey:AEGZUDTUCOLGLE-UHFFFAOYSA-N
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Compound 89
Molecular Weight:334.3239
Molecular Formula:C16H18N2O6
InChIKey:SVCMELBDAIJMTR-UHFFFAOYSA-N
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Compound 90
Molecular Weight:336.3398
Molecular Formula:C16H20N2O6
InChIKey:CIROPWOAIAHUJE-UHFFFAOYSA-N
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Compound 91
Molecular Weight:332.457
Molecular Formula:C19H24O3S
InChIKey:JBJGMPLEUTTZPD-UHFFFAOYSA-N
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Compound 92
Molecular Weight:306.42
Molecular Formula:C17H22O3S
InChIKey:NXWLBPXMYIJVPC-UHFFFAOYSA-N
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Compound 93
Molecular Weight:301.3371
Molecular Formula:C17H19NO4
InChIKey:YZLNOEWUNSTJQR-UHFFFAOYSA-N
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Compound 94
Molecular Weight:335.3533
Molecular Formula:C20H17NO4
InChIKey:NUPCIYHZMIBVSW-UHFFFAOYSA-N
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Compound 95
Molecular Weight:349.3799
Molecular Formula:C21H19NO4
InChIKey:OQVRBENXOMCYLN-UHFFFAOYSA-N
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Compound 96
Molecular Weight:122.2075
Molecular Formula:C9H14
InChIKey:LMWNLUONWYANKL-UHFFFAOYSA-N
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Compound 97
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 101
Molecular Weight:110.1968
Molecular Formula:C8H14
InChIKey:FOEYMRPOKBCNCR-UHFFFAOYSA-N
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Compound 103
Molecular Weight:106.165
Molecular Formula:C8H10
InChIKey:YNQLUTRBYVCPMQ-UHFFFAOYSA-N
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Compound 104
Molecular Weight:106.165
Molecular Formula:C8H10
InChIKey:YNQLUTRBYVCPMQ-UHFFFAOYSA-N
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Compound 114-F
Molecular Weight:123.147
Molecular Formula:C8H8F
InChIKey:HGIAQOSHDISSGN-UHFFFAOYSA-N
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Compound 121
Molecular Weight:214.3448
Molecular Formula:C16H22
InChIKey:SUXLZVTUCNUCKJ-UHFFFAOYSA-N
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Compound 122
Molecular Weight:372.4998
Molecular Formula:C29H24
InChIKey:ISUSOPKOUWTNIJ-UHFFFAOYSA-N
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Compound 123
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 125
Molecular Weight:124.2222
Molecular Formula:C9H16
InChIKey:FZARCFVSSLLEJK-UHFFFAOYSA-N
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Compound 127
Molecular Weight:228.3714
Molecular Formula:C17H24
InChIKey:RTCNLHGKFIBDPR-UHFFFAOYSA-N
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Compound 129
Molecular Weight:260.3713
Molecular Formula:C17H24O2
InChIKey:JJWWCHMULFYRRR-UHFFFAOYSA-N
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Compound 130
Molecular Weight:258.3554
Molecular Formula:C17H22O2
InChIKey:HTHRIUVWIOJOQD-UHFFFAOYSA-N
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Compound 128
Molecular Weight:262.3871
Molecular Formula:C17H26O2
InChIKey:LWAZFEBGKPFMEW-UHFFFAOYSA-N
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Compound 131
Molecular Weight:194.701
Molecular Formula:C12H15Cl
InChIKey:AEOWEUFNSCGQLA-UHFFFAOYSA-N
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Compound 132
Molecular Weight:154.637
Molecular Formula:C9H11Cl
InChIKey:KPJKMUJJFXZGAX-UHFFFAOYSA-N
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Compound 133
Molecular Weight:172.2661
Molecular Formula:C13H16
InChIKey:ZPJDEKDFDRVYFE-KHPPLWFESA-N
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Compound 134
Molecular Weight:172.2661
Molecular Formula:C13H16
InChIKey:ZPJDEKDFDRVYFE-ZHACJKMWSA-N
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Compound 135
Molecular Weight:147.1932
Molecular Formula:C10H11O
InChIKey:HNSKLKNMMFTYNJ-UHFFFAOYSA-N
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Compound 136
Molecular Weight:111.1611
Molecular Formula:C7H11O
InChIKey:ROWAYGAXUZJNKH-UHFFFAOYSA-N
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Compound 137
Molecular Weight:149.2521
Molecular Formula:C11H17
InChIKey:PGKSBVUNCWCJAR-UHFFFAOYSA-N
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Compound 138
Molecular Weight:85.1238
Molecular Formula:C5H9O
InChIKey:GCKAOOUVLWHVCN-UHFFFAOYSA-N
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Compound 139
Molecular Weight:99.1504
Molecular Formula:C6H11O
InChIKey:UNZKLOKNOWXRGC-UHFFFAOYSA-N
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Compound 140
Molecular Weight:111.1611
Molecular Formula:C7H11O
InChIKey:BMXJJDJVIOQPNB-UHFFFAOYSA-N
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  1. 1 - 93