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The Preparation of Organolithium Reagents and Intermediates

Organolithium Compounds (2004)

  1. Frédéric Leroux1,
  2. Manfred Schlosser2,
  3. Elinor Zohar3,
  4. Ilan Marek3

Published Online: 15 DEC 2009

DOI: 10.1002/9780470682531.pat0305

Patai's Chemistry of Functional Groups

Patai's Chemistry of Functional Groups

How to Cite

Leroux, F., Schlosser, M., Zohar, E. and Marek, I. 2009. The Preparation of Organolithium Reagents and Intermediates. Patai's Chemistry of Functional Groups. .

Author Information

  1. 1

    Université Louis Pasteur (ECPM), Laboratoire de stéréochimie, Strasbourg, France

  2. 2

    Swiss Federal Institute of Technology, Institute of Molecular and Biological Chemistry, Lausanne, Switzerland

  3. 3

    Technion—Israel Institute of Technology, Department of Chemistry and Institute of Catalysis, Science and Technology, Haifa, Israel

Publication History

  1. Published Online: 15 DEC 2009

Abstract

  • 1
    Introduction
  • 2
    Reductive Metal Insertion into Carbon–Halogen Bonds
  • 3
    Permutational Halogen/Metal Interconversions
  • 4
    Permutational Hydrogen/Metal Interconversions (‘Metalations’)
  • 5
    The Brook Isomerization
  • 6
    The Shapiro Reaction
  • 7
    The Sulfoxide/Lithium Displacement
  • 8
    Acknowledgments

Keywords:

  • organolithium reagents and intermediates;
  • permutational halogen/metal interconversions;
  • primary aliphatic organolithiums;
  • permutational hydrogen/metal interconversions;
  • Brook isomerization;
  • Shapiro reaction;
  • sulfoxide/lithium displacement;
  • alkenyl sulfoxide and sulfoxide–lithium exchange reaction

Featured Compounds

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  1. 1 - 155
Compound 87
Molecular Weight:64.055
Molecular Formula:C4H9Li
InChIKey:MZRVEZGGRBJDDB-UHFFFAOYSA-N
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Compound 2
Molecular Weight:142.167
Molecular Formula:C10H15Li
InChIKey:ACSFSGORTGKAJW-UHFFFAOYSA-N
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Compound 91
Molecular Weight:88.077
Molecular Formula:C6H9Li
InChIKey:FGWXZSMNTXJKPR-UHFFFAOYSA-N
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Compound 1
Molecular Weight:262.1306
Molecular Formula:C10H15I
InChIKey:PXVOATXCSSPUEM-UHFFFAOYSA-N
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Compound 105
Molecular Weight:86.1323
Molecular Formula:C5H10O
InChIKey:FDPIMTJIUBPUKL-UHFFFAOYSA-N
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Compound 3
Molecular Weight:277.941
Molecular Formula:C8H6Br2O
InChIKey:NJQJUJHJJZMVNB-UHFFFAOYSA-N
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Compound 4
Molecular Weight:565.9154
Molecular Formula:C11H9I3N2O
InChIKey:CEYZKDWPXOUDDM-UHFFFAOYSA-N
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Compound 5
Molecular Weight:434.949
Molecular Formula:C14H11Br3O
InChIKey:SFNAOGOPUIRQNH-UHFFFAOYSA-N
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Compound 6
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 7
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 8
Molecular Weight:173.299
Molecular Formula:C9H23N3
InChIKey:UKODFQOELJFMII-UHFFFAOYSA-N
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Compound 9
Molecular Weight:171.2368
Molecular Formula:C9H17NO2
InChIKey:LPQZERIRKRYGGM-UHFFFAOYSA-N
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Compound 10
Molecular Weight:228.4463
Molecular Formula:C13H28OSi
InChIKey:JVRWBVQTNCPSTP-OLZOCXBDSA-N
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Compound 11
Molecular Weight:157.2102
Molecular Formula:C8H15NO2
InChIKey:VQLIJOWSVJKBFP-UHFFFAOYSA-N
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Compound 12
Molecular Weight:185.2634
Molecular Formula:C10H19NO2
InChIKey:HDTFEWPWKHBMDX-UHFFFAOYSA-N
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Compound 13
Molecular Weight:211.3006
Molecular Formula:C12H21NO2
InChIKey:BQDXAJQNMXFTJA-UHFFFAOYSA-N
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Compound 14a
Molecular Weight:145.1613
Molecular Formula:C8H7N3
InChIKey:OKHGMSQINQQCIE-UHFFFAOYSA-N
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Compound 14b
Molecular Weight:159.1879
Molecular Formula:C9H9N3
InChIKey:DRWHCTRTNUOACY-UQCOIBPSSA-N
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Compound 14c
Molecular Weight:159.1879
Molecular Formula:C9H9N3
InChIKey:DRWHCTRTNUOACY-FARCUNLSSA-N
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Compound 15
Molecular Weight:198.3482
Molecular Formula:C12H26N2
InChIKey:XQDSZJSQHHRZDE-MDZDMXLPSA-N
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Compound 16
Molecular Weight:182.3058
Molecular Formula:C11H22N2
InChIKey:LZMBCHDFEZTJII-UHFFFAOYSA-N
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Compound 17
Molecular Weight:113.2007
Molecular Formula:C7H15N
InChIKey:MDFOQCKFSUMLET-UHFFFAOYSA-N
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Compound 18
Molecular Weight:129.2755
Molecular Formula:C6H15NSi
InChIKey:FFJKAASRNUVNRT-UHFFFAOYSA-N
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Compound 14
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 19b
Molecular Weight:72.1057
Molecular Formula:C4H8O
InChIKey:FJKIXWOMBXYWOQ-UHFFFAOYSA-N
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Compound 20
Molecular Weight:116.1583
Molecular Formula:C6H12O2
InChIKey:HLOSVYMHSXUVEM-UHFFFAOYSA-N
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Compound 21
Molecular Weight:164.2011
Molecular Formula:C10H12O2
InChIKey:ZALWPGMCEPAOFB-UHFFFAOYSA-N
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Compound 22
Molecular Weight:152.2334
Molecular Formula:C10H16O
InChIKey:BKOJSFOZFOXOGG-UHFFFAOYSA-N
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Compound 23
Molecular Weight:154.2493
Molecular Formula:C10H18O
InChIKey:CDOSHBSSFJOMGT-UHFFFAOYSA-N
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Compound 19
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 24
Molecular Weight:82.0245
Molecular Formula:C2HF3
InChIKey:MIZLGWKEZAPEFJ-UHFFFAOYSA-N
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Compound 25
Molecular Weight:140.13
Molecular Formula:C8H6F2
InChIKey:MRYRJRWSHBRIDR-SOFGYWHQSA-N
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Compound 26
Molecular Weight:162.2201
Molecular Formula:C9H16F2
InChIKey:BZVVAVVEEQITSM-HJWRWDBZSA-N
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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:192.3296
Molecular Formula:C11H16OSi
InChIKey:BCRZWEQCCUZXKL-UHFFFAOYSA-N
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Compound 30
Molecular Weight:176.162
Molecular Formula:C8H9LiO2S
InChIKey:CVMBHCCOALYSGQ-UHFFFAOYSA-N
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Compound 33
Molecular Weight:220.3828
Molecular Formula:C13H20OSi
InChIKey:KHOVUSCANSSXLT-ACAGNQJTSA-N
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Compound 34
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 35
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 36a
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 36b
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 39
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 37
Molecular Weight:258.4308
Molecular Formula:C16H22OSi
InChIKey:STVHSRVAHOQBFK-UHFFFAOYSA-N
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Compound 40
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 38
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 41
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 42
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 43
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 44
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 45
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 46
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 47
Molecular Weight:158.3134
Molecular Formula:C8H18OSi
InChIKey:LGOXIFWKYQZGSV-UHFFFAOYSA-N
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Compound 49
Molecular Weight:163.056
Molecular Formula:C6H11Br
InChIKey:ZODGKVNNDFRQMS-UHFFFAOYSA-N
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Compound 50
Molecular Weight:282.5368
Molecular Formula:C17H34OSi
InChIKey:BDIJSXYMAFWYBI-NXVVXOECSA-N
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Compound 51
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 52
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 53
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 54
Molecular Weight:116.087
Molecular Formula:C7H9LiO
InChIKey:YRMNNAORRZIRGC-UHFFFAOYSA-M
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Compound 55
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 56
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 57
Molecular Weight:183.251
Molecular Formula:C10H14LiNSi
InChIKey:IQEXMLPCGWHMTF-UHFFFAOYSA-N
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Compound 58
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 59
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 60
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 61
Molecular Weight:275.5044
Molecular Formula:C17H29NSi
InChIKey:RUKDQWVRVYAWIJ-NTCAYCPXSA-N
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Compound 62
Molecular Weight:289.5309
Molecular Formula:C18H31NSi
InChIKey:ZKKYUYJGQRLEEG-NXVVXOECSA-N
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Compound 63
Molecular Weight:281.437
Molecular Formula:C17H28LiNSi
InChIKey:FCNDOPWKOOFGKU-UNVLYCKESA-N
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Compound 64
Molecular Weight:288.095
Molecular Formula:C7H16Br2Si
InChIKey:XINIZQRUNWPXNM-UHFFFAOYSA-N
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Compound 66
Molecular Weight:506.272
Molecular Formula:C21H27Br2LiO2Si
InChIKey:YPMJDINEYCFRBZ-UHFFFAOYSA-N
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Compound 65
Molecular Weight:400.15
Molecular Formula:C14H21Br2LiOSi
InChIKey:BSAQTMUBDKYISU-UHFFFAOYSA-N
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Compound 68
Molecular Weight:165.235
Molecular Formula:C7H16LiNOSi
InChIKey:NYKMTLHOSGCJHN-UHDJGPCESA-M
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Compound 67
Molecular Weight:159.3015
Molecular Formula:C7H17NOSi
InChIKey:XHZOOXCBXCLEGI-UHFFFAOYSA-N
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Compound 71
Molecular Weight:217.3806
Molecular Formula:C10H23NO2Si
InChIKey:PKVCJULFISGIQR-UHFFFAOYSA-N
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Compound 70
Molecular Weight:223.314
Molecular Formula:C10H22LiNO2Si
InChIKey:IAJIKYZWPIYPJG-UHFFFAOYSA-N
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Compound 72
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 73
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 74
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 77
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 75
Molecular Weight:192.417
Molecular Formula:C7H16S2Si
InChIKey:BTTUMVHWIAXYPJ-UHFFFAOYSA-N
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Compound 76
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 78
Molecular Weight:234.497
Molecular Formula:C10H22S2Si
InChIKey:Not Available
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Compound 79
Molecular Weight:164.2011
Molecular Formula:C10H12O2
InChIKey:QNYBOILAKBSWFG-JTQLQIEISA-N
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Compound 80
Molecular Weight:404.631
Molecular Formula:C20H33LiO2S2Si
InChIKey:XQMYTLQSVZCREJ-GMUIIQOCSA-N
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Compound 81
Molecular Weight:92.524
Molecular Formula:C3H5ClO
InChIKey:BRLQWZUYTZBJKN-VKHMYHEASA-N
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Compound 82
Molecular Weight:853.46
Molecular Formula:C43H72O5S4Si2
InChIKey:MHBFSZJOLKRXGL-LJEWAXOPSA-N
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Compound 83
Molecular Weight:295.4542
Molecular Formula:C17H21N3Si
InChIKey:NSHDRTMLUUGTBQ-UHFFFAOYSA-N
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Compound 85
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 86
Molecular Weight:266.359
Molecular Formula:C13H18N2O2S
InChIKey:WMCVYCATQIGYIO-UHFFFAOYSA-N
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Compound 88
Molecular Weight:272.292
Molecular Formula:C13H17LiN2O2S
InChIKey:XEPNSHPPQIMRSI-UHFFFAOYSA-N
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Compound 89
Molecular Weight:278.225
Molecular Formula:C13H16Li2N2O2S
InChIKey:JVCDDZSGIDOXKX-QHXCTMFKSA-N
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Compound 90
Molecular Weight:116.09
Molecular Formula:C6H9LiN2
InChIKey:IFDMUOBUMLAFHH-UHFFFAOYSA-N
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Compound 92
Molecular Weight:82.1436
Molecular Formula:C6H10
InChIKey:HGCIXCUEYOPUTN-UHFFFAOYSA-N
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Compound 93
Molecular Weight:284.158
Molecular Formula:C13H15Li3N2O2S
InChIKey:CGGZQGOLXUVTLS-XPGLNUPKSA-N
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Compound 94
Molecular Weight:298.444
Molecular Formula:C15H26N2O2S
InChIKey:UGRVYFQFDZRNMQ-UHFFFAOYSA-N
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Compound 95
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 96
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 97
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 98
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 99
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 100
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 101
Molecular Weight:102.103
Molecular Formula:C7H11Li
InChIKey:URXKOVVBCINRNG-UHFFFAOYSA-N
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Compound 102
Molecular Weight:76.066
Molecular Formula:C5H9Li
InChIKey:HMXZECUBAKAJKT-UHFFFAOYSA-N
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Compound 103
Molecular Weight:308.439
Molecular Formula:C16H24N2O2S
InChIKey:KVEVUBBHNJCPDD-SAPNQHFASA-N
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Compound 104
Molecular Weight:320.45
Molecular Formula:C17H24N2O2S
InChIKey:CYHKGLOXAZMDCN-RRNJOWJLSA-N
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Compound 106
Molecular Weight:76.066
Molecular Formula:C5H9Li
InChIKey:WHILWMFGDYCBIA-UHFFFAOYSA-N
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Compound 109
Molecular Weight:338.508
Molecular Formula:C18H30N2O2S
InChIKey:DQJLVAMQVPQQGF-UHFFFAOYSA-N
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Compound 110
Molecular Weight:350.374
Molecular Formula:C18H28Li2N2O2S
InChIKey:RNKZUTNZGLTMPA-ZWXFCGGNSA-N
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Compound 111
Molecular Weight:414.574
Molecular Formula:C23H39LiN2O2S
InChIKey:VJMOVVHQOBUVHO-BMGIYVBOSA-N
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Compound 112
Molecular Weight:420.507
Molecular Formula:C23H38Li2N2O2S
InChIKey:DKCCMBYOCVYEOX-NABJOEGNSA-N
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Compound 113
Molecular Weight:118.146
Molecular Formula:C8H15Li
InChIKey:DSOQNAZJXBUQTR-UHFFFAOYSA-N
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Compound 114
Molecular Weight:128.212
Molecular Formula:C8H16O
InChIKey:ZPVFWPFBNIEHGJ-UHFFFAOYSA-N
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Compound 115
Molecular Weight:118.146
Molecular Formula:C8H15Li
InChIKey:YHBVLQVMBVGUIO-UHFFFAOYSA-N
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Compound 116
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 117
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 119
Molecular Weight:258.3984
Molecular Formula:C18H26O
InChIKey:PXGUDEXENWIANN-MHWRWJLKSA-N
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Compound 120
Molecular Weight:478.616
Molecular Formula:C27H39LiN2O3S
InChIKey:MRHTUPYWZODWDP-AYYDQZPKSA-N
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Compound 121
Molecular Weight:484.549
Molecular Formula:C27H38Li2N2O3S
InChIKey:WANVTYMFBBGRFX-POWVFBIKSA-N
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Compound 122Cu
Molecular Weight:354.883
Molecular Formula:C17H18CuLiNOS
InChIKey:AEOVUHUOJJAYNF-UHFFFAOYSA-N
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Compound 122Li
Molecular Weight:182.188
Molecular Formula:C12H15LiO
InChIKey:CNUKSLIKRRSJEJ-UHFFFAOYSA-N
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Compound 124
Molecular Weight:352.535
Molecular Formula:C19H32N2O2S
InChIKey:IWUVUJNQBJEKQR-HMMYKYKNSA-N
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Compound 123
Molecular Weight:72.1057
Molecular Formula:C4H8O
InChIKey:ZEXFAVZTIZXHFA-ONEGZZNKSA-N
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Compound 126
Molecular Weight:309.241
Molecular Formula:C16H21BrO
InChIKey:QVJUJSJTBSJZES-VGOFMYFVSA-N
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Compound 125Li
Molecular Weight:196.214
Molecular Formula:C13H17LiO
InChIKey:MVWJIXAKWPJWJH-UHFFFAOYSA-N
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Compound 129
Molecular Weight:254.4082
Molecular Formula:C16H30O2
InChIKey:XXPBOEBNDHAAQH-SREVYHEPSA-N
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Compound 127
Molecular Weight:216.322
Molecular Formula:C14H20N2
InChIKey:UNHVMXIJQJUFQP-NTCAYCPXSA-N
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Compound 128
Molecular Weight:458.7949
Molecular Formula:C28H50N2OSi
InChIKey:FLSLDNWYFUWWGN-WCTVFOPTSA-N
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Compound 130
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 133
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 132
Molecular Weight:182.283
Molecular Formula:C10H14OS
InChIKey:IMRHEMHQODDESO-UHFFFAOYSA-N
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Compound 131
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 134
Molecular Weight:334.431
Molecular Formula:C21H18O2S
InChIKey:LJCWMTGLSUMVPS-YHNKWQPZSA-N
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Compound 135
Molecular Weight:334.431
Molecular Formula:C21H18O2S
InChIKey:LJCWMTGLSUMVPS-LDJQHZOJSA-N
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Compound 136
Molecular Weight:210.2711
Molecular Formula:C15H14O
InChIKey:ZMEQMWLSJBXCMR-LSDHHAIUSA-N
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Compound 137
Molecular Weight:210.2711
Molecular Formula:C15H14O
InChIKey:ZMEQMWLSJBXCMR-GJZGRUSLSA-N
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Compound 138
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 139
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 140
Molecular Weight:333.447
Molecular Formula:C21H19NOS
InChIKey:BTLHWLDYMJGRQA-NJRHGXBZSA-N
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Compound 141
Molecular Weight:215.219
Molecular Formula:C15H14LiN
InChIKey:YPJZOIYLLPEMET-VPVGQWTESA-N
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Compound 142
Molecular Weight:378.506
Molecular Formula:C19H22O4S2
InChIKey:GQGNXGJLRVMCSD-QBROUFQSSA-N
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Compound 143
Molecular Weight:158.2396
Molecular Formula:C12H14
InChIKey:MMOPZNIENWEZPU-UHFFFAOYSA-N
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Compound 145
Molecular Weight:314.442
Molecular Formula:C19H22O2S
InChIKey:SNDMGRXDSJKYLB-UHFFFAOYSA-N
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Compound 144
Molecular Weight:182.283
Molecular Formula:C10H14OS
InChIKey:WNXVEFMOQSAQJV-UHFFFAOYSA-N
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Compound 146
Molecular Weight:222.346
Molecular Formula:C13H18OS
InChIKey:NPDJZUXSZRMTKC-UHFFFAOYSA-N
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Compound 148
Molecular Weight:158.2396
Molecular Formula:C12H14
InChIKey:LQEWBMUGVVQIHH-UHFFFAOYSA-N
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Compound 149
Molecular Weight:198.3034
Molecular Formula:C15H18
InChIKey:RXIAXTKFOJTKJE-UHFFFAOYSA-N
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Compound 152
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 153
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 150
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 151
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 154
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 155
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 158
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 157
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 156
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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