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Synthesis of Anilines

Anilines (2007)

  1. John F. Hartwig,
  2. Shashank Shekhar,
  3. Qilong Shen,
  4. Fabiola Barrios-Landeros

Published Online: 15 DEC 2009

DOI: 10.1002/9780470682531.pat0391

Patai's Chemistry of Functional Groups

Patai's Chemistry of Functional Groups

How to Cite

Hartwig, J. F., Shekhar, S., Shen, Q. and Barrios-Landeros, F. 2009. Synthesis of Anilines. Patai's Chemistry of Functional Groups. .

Author Information

  1. Yale University, Department of Chemistry, New Haven, Connecticut, USA

  1. Current Address: A410 CLSL, Box 58-6, MC-712, Department of Chemistry, University of Illinois, 600 South Mathews Av., Urbana, Illinois 61801, USA. Fax: 217-244-8024; e-mail: jhartwig@uiuc.edu

Publication History

  1. Published Online: 15 DEC 2009

Abstract

  • 1
    Introduction
  • 2
    Uncatalyzed Reactions
  • 3
    Palladium-Catalyzed Methods
  • 4
    Mechanism of Palladium-Catalyzed Amination of Aryl Halides
  • 5
    Copper-Mediated Methods
  • 6
    Mechanism of Copper-Mediated/Catalyzed Reactions

Keywords:

  • aromatic amines;
  • direct nucleophilic substitution;
  • palladium-catalyzed methods;
  • ligand aniline arylation;
  • palladium-catalyzed arylation;
  • functionalized aryl bromide reactions;
  • aryl halide palladium-catalyzed amination mechanism;
  • copper-mediated methods

Featured Compounds

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  1. 1 - 107
Compound 1
Molecular Weight:616.548
Molecular Formula:C21H27Na3O9PS3
InChIKey:LCDPAEBECORMBA-UHFFFAOYSA-K
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Compound 2
Molecular Weight:1439.299
Molecular Formula:C50H52Na4O24P2S8
InChIKey:NZIWDAFQRWXGJK-UHFFFAOYSA-F
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Compound 3
Molecular Weight:304.3652
Molecular Formula:C21H21P
InChIKey:COIOYMYWGDAQPM-UHFFFAOYSA-N
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Compound 4
Molecular Weight:554.379
Molecular Formula:C34H28FeP2
InChIKey:Not Available
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Compound 5
Molecular Weight:622.6724
Molecular Formula:C44H32P2
InChIKey:Not Available
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Compound 6
Molecular Weight:578.6183
Molecular Formula:C39H32OP2
InChIKey:CXNIUSPIQKWYAI-UHFFFAOYSA-N
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Compound 7
Molecular Weight:506.396
Molecular Formula:C31H31FeOP
InChIKey:CPXQTIASMRZZKA-UHFFFAOYSA-N
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Compound 8
Molecular Weight:393.5445
Molecular Formula:C26H36NP
InChIKey:ZEMZPXWZVTUONV-UHFFFAOYSA-N
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Compound 9a
Molecular Weight:348.3747
Molecular Formula:C22H21O2P
InChIKey:IAEFMXYVOKQBEA-UHFFFAOYSA-N
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Compound 9b
Molecular Weight:360.47
Molecular Formula:C22H33O2P
InChIKey:ZQASITYRQOCACA-UHFFFAOYSA-N
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Compound 10a
Molecular Weight:412.5063
Molecular Formula:C27H29N2P
InChIKey:VKWQKEOBEYGWFN-UHFFFAOYSA-N
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Compound 10b
Molecular Weight:440.5595
Molecular Formula:C29H33N2P
InChIKey:JAIIBHBCNPAPPF-UHFFFAOYSA-N
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Compound 11
Molecular Weight:469.4328
Molecular Formula:C25H24CrNO3P
InChIKey:QFFWSFAKWADVTP-DEXDRMDJSA-N
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Compound 12
Molecular Weight:350.4767
Molecular Formula:C24H31P
InChIKey:LCSNDSFWVKMJCT-UHFFFAOYSA-N
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Compound 13
Molecular Weight:298.4021
Molecular Formula:C20H27P
InChIKey:CNXMDTWQWLGCPE-UHFFFAOYSA-N
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Compound 14
Molecular Weight:710.706
Molecular Formula:C48H47FeP
InChIKey:BOBUBHOXRCYKLI-UHFFFAOYSA-N
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Compound 15
Molecular Weight:202.3165
Molecular Formula:C12H27P
InChIKey:BWHDROKFUHTORW-UHFFFAOYSA-N
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Compound 16
Molecular Weight:292.3099
Molecular Formula:C16H21O3P
InChIKey:Not Available
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Compound 17
Molecular Weight:300.4231
Molecular Formula:C15H33N4P
InChIKey:NTSXQHCKGLSIFB-UHFFFAOYSA-N
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Compound 18
Molecular Weight:388.5881
Molecular Formula:C27H36N2
InChIKey:NJLYZISHBSABMZ-UHFFFAOYSA-N
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Compound 19
Molecular Weight:474.42
Molecular Formula:C26H44FeP2
InChIKey:WDUDHEOUGWAKFD-UHFFFAOYSA-N
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Compound 20
Molecular Weight:337.4382
Molecular Formula:C22H28NP
InChIKey:HDZRDZCQFYUOHE-UHFFFAOYSA-N
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Compound 21
Molecular Weight:358.5402
Molecular Formula:C24H39P
InChIKey:Not Available
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Compound 22
Molecular Weight:180.2899
Molecular Formula:C11H20N2
InChIKey:WLZCDCXFXATHNC-UHFFFAOYSA-N
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Compound 23
Molecular Weight:388.5881
Molecular Formula:C27H36N2
InChIKey:NJLYZISHBSABMZ-UHFFFAOYSA-N
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Compound 24
Molecular Weight:390.604
Molecular Formula:C27H38N2
InChIKey:UWINQFQLMRKGBB-UHFFFAOYSA-N
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Compound 25
Molecular Weight:304.4287
Molecular Formula:C21H24N2
InChIKey:RSTLYZXJMXWXEI-UHFFFAOYSA-N
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Compound 26
Molecular Weight:306.4445
Molecular Formula:C21H26N2
InChIKey:RUKVGXGTVPPWDD-UHFFFAOYSA-N
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Compound 27
Molecular Weight:1131.83
Molecular Formula:C54H72Cl4N4Pd2
InChIKey:SVEFZTWWVKPRCY-UHFFFAOYSA-J
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Compound 28
Molecular Weight:571.53
Molecular Formula:C30H41ClN2Pd
InChIKey:IAFSDYZUSXUILS-UHFFFAOYSA-M
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Compound 29
Molecular Weight:490.38
Molecular Formula:C23H30ClN3Pd
InChIKey:VZQZODQEBFAFBD-UHFFFAOYSA-M
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Compound 30
Molecular Weight:1306.32
Molecular Formula:C74H84N4O4Pd2
InChIKey:OWDKNIPDMAILCL-UHFFFAOYSA-N
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Compound 31
Molecular Weight:476.7159
Molecular Formula:C33H49P
InChIKey:Not Available
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Compound 32
Molecular Weight:554.548
Molecular Formula:C32H52FeP2
InChIKey:XUGHPTFNSLEKBM-GHVWMZMZSA-N
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Compound 33
Molecular Weight:576.6455
Molecular Formula:C40H34P2
InChIKey:GYZZZILPVUYAFJ-UHFFFAOYSA-N
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Compound 34
Molecular Weight:538.5544
Molecular Formula:C36H28OP2
InChIKey:RYXZOQOZERSHHQ-UHFFFAOYSA-N
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Compound 35
Molecular Weight:481.5666
Molecular Formula:C34H28NP
InChIKey:VJCICCSVPBEHDK-UHFFFAOYSA-N
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Compound 36
Molecular Weight:870.07
Molecular Formula:C48H41FeN2P2Pd
InChIKey:XNBMFPOINYFRMU-UHFFFAOYSA-N
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Compound 37
Molecular Weight:860.09
Molecular Formula:C48H45FeNP2Pd
InChIKey:WHSOSXDMVJXGHW-UHFFFAOYSA-N
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Compound 38
Molecular Weight:937.64
Molecular Formula:C46H46O4P2Pd2
InChIKey:YRGPDGDJUOTURS-UHFFFAOYSA-L
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Compound 40
Molecular Weight:634.06
Molecular Formula:C29H45F3NO2PPd
InChIKey:IADZMQWQCHTGAE-UHFFFAOYSA-M
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Compound 41
Molecular Weight:704.11
Molecular Formula:C35H43F3NO2PPd
InChIKey:VPOLNLPHOBYWAS-UHFFFAOYSA-M
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Compound 39
Molecular Weight:707.27
Molecular Formula:C22H24F6N2O4Pd2
InChIKey:FJGILSMHTJBPBB-UHFFFAOYSA-L
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Compound 42a
Molecular Weight:1068.22
Molecular Formula:C60H95ClO3P2Pd
InChIKey:KSWCAUMOXBNXFL-UHFFFAOYSA-M
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Compound 42b
Molecular Weight:990.1
Molecular Formula:C54H89ClO3P2Pd
InChIKey:VNUZVOONVPFAFI-UHFFFAOYSA-M
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Compound 43
Molecular Weight:733.68
Molecular Formula:C38H57ClOP2Pd
InChIKey:UWKDNRKTFRYAQD-UHFFFAOYSA-M
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Compound 44
Molecular Weight:462.86
Molecular Formula:C22H29O2PPd
InChIKey:IEYDYAASBZOBOC-UHFFFAOYSA-M
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Compound 45b
Molecular Weight:484.35
Molecular Formula:C22H33ClNPPd
InChIKey:WQPHAYLOTOIPGL-UHFFFAOYSA-M
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Compound 45c
Molecular Weight:536.43
Molecular Formula:C26H37ClNPPd
InChIKey:AGBCSUVLKDAWMI-UHFFFAOYSA-M
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Compound 45d
Molecular Weight:618.57
Molecular Formula:C32H47ClNPPd
InChIKey:KFZBMTPURPAMEL-UHFFFAOYSA-M
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Compound 46
Molecular Weight:606.3
Molecular Formula:C27H39ClFeNPPd
InChIKey:XQCLJPQVPAENBE-UHFFFAOYSA-M
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Compound 47
Molecular Weight:442.594
Molecular Formula:C26H35O2PS
InChIKey:HIXJVXJBIZWQHT-UHFFFAOYSA-N
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Compound 48
Molecular Weight:506.6606
Molecular Formula:C34H39N2P
InChIKey:ZZVXGCKPGOHZKG-UHFFFAOYSA-N
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Compound 49
Molecular Weight:376.514
Molecular Formula:C26H33P
InChIKey:YYPUOXYVBWNLGO-UHFFFAOYSA-N
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Compound 50
Molecular Weight:1051.6
Molecular Formula:C56H74F3O3P2PdS
InChIKey:CSAJREZWYZXIIF-UHFFFAOYSA-M
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Compound 51
Molecular Weight:162.2096
Molecular Formula:C8H19OP
InChIKey:RYLNFGJYRKJXQE-UHFFFAOYSA-N
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Compound 52a
Molecular Weight:671.05
Molecular Formula:C20H27Br2PPd2
InChIKey:NLOKIFMUKXHJBA-UHFFFAOYSA-L
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Compound 52b
Molecular Weight:582.15
Molecular Formula:C20H27Cl2PPd2
InChIKey:VTVPHVNKBSPZLL-UHFFFAOYSA-L
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Compound 53
Molecular Weight:543.86
Molecular Formula:C24H38BrPPd
InChIKey:DZHWFHBUIVDSAK-UHFFFAOYSA-M
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Compound 54
Molecular Weight:540.8
Molecular Formula:C20H36IPPd
InChIKey:IPTRFYAEMNKGRE-UHFFFAOYSA-M
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Compound 55b
Molecular Weight:844.05
Molecular Formula:C47H41FeNP2Pd
InChIKey:ICIKZKORENQKRF-UHFFFAOYSA-N
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Compound 55c
Molecular Weight:824.06
Molecular Formula:C45H45FeNP2Pd
InChIKey:HDBHEFWKYSUQRR-UHFFFAOYSA-N
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Compound 56a
Molecular Weight:926.07
Molecular Formula:C49H42F3FeNP2Pd
InChIKey:PPZSMCVHRTWYAL-UHFFFAOYSA-N
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Compound 56b
Molecular Weight:912.05
Molecular Formula:C48H40F3FeNP2Pd
InChIKey:SKMRIXCHQBEDRI-UHFFFAOYSA-N
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Compound 56c
Molecular Weight:942.07
Molecular Formula:C49H42F3FeNOP2Pd
InChIKey:NCOLKTKYFMODFR-UHFFFAOYSA-N
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Compound 57
Molecular Weight:1046.18
Molecular Formula:C53H50F3FeNO4P2Pd
InChIKey:DBMSBKNWUBOGLI-UHFFFAOYSA-N
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Compound 58
Molecular Weight:1198.06
Molecular Formula:C53H38F15FeNP2Pd
InChIKey:DZWDQVJKWLTOEX-UHFFFAOYSA-N
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Compound 59
Molecular Weight:986.12
Molecular Formula:C51H46F3FeNO2P2Pd
InChIKey:SCOYDZJHZIQKPX-UHFFFAOYSA-N
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Compound 60
Molecular Weight:1062.07
Molecular Formula:C51H40F9FeNP2Pd
InChIKey:AZYOUKRCYPZQJI-UHFFFAOYSA-N
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Compound 61
Molecular Weight:1122.12
Molecular Formula:C53H44F9FeNO2P2Pd
InChIKey:KQKIVEGMHQUHKL-UHFFFAOYSA-N
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Compound 62
Molecular Weight:180.2053
Molecular Formula:C12H8N2
InChIKey:DGEZNRSVGBDHLK-UHFFFAOYSA-N
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Compound 63
Molecular Weight:280.3675
Molecular Formula:C17H20N4
InChIKey:TWFQORMKVVGZPJ-UHFFFAOYSA-N
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Compound 64
Molecular Weight:122.1644
Molecular Formula:C8H10O
InChIKey:Not Available
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Compound 65
Molecular Weight:170.2072
Molecular Formula:C12H10O
InChIKey:LLEMOWNGBBNAJR-UHFFFAOYSA-N
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Compound 66
Molecular Weight:170.2072
Molecular Formula:C12H10O
InChIKey:LLEMOWNGBBNAJR-UHFFFAOYSA-N
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Compound 67
Molecular Weight:171.1953
Molecular Formula:C11H9NO
InChIKey:HPDNGBIRSIWOST-UHFFFAOYSA-N
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Compound 68
Molecular Weight:163.1733
Molecular Formula:C9H9NO2
InChIKey:FETLPNKZRXDWLT-UHFFFAOYSA-N
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Compound 69
Molecular Weight:137.136
Molecular Formula:C7H7NO2
InChIKey:SKZKKFZAGNVIMN-UHFFFAOYSA-N
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Compound 70
Molecular Weight:134.1751
Molecular Formula:C9H10O
InChIKey:QIRNGVVZBINFMX-UHFFFAOYSA-N
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Compound 71
Molecular Weight:121.1366
Molecular Formula:C7H7NO
InChIKey:KXDAEFPNCMNJSK-UHFFFAOYSA-N
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Compound 72
Molecular Weight:236.3116
Molecular Formula:C16H16N2
InChIKey:QBAKBJNOARBSGP-HBKJEHTGSA-N
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Compound 73
Molecular Weight:122.1246
Molecular Formula:C6H6N2O
InChIKey:IBBMAWULFFBRKK-UHFFFAOYSA-N
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Compound 74
Molecular Weight:193.2423
Molecular Formula:C11H15NO2
InChIKey:ZVYXEXAXXWINEH-UHFFFAOYSA-N
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Compound 75
Molecular Weight:214.2167
Molecular Formula:C13H10O3
InChIKey:ZQBAKBUEJOMQEX-UHFFFAOYSA-N
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Compound 76
Molecular Weight:165.1891
Molecular Formula:C9H11NO2
InChIKey:UBAYZMJYXBTDBB-UHFFFAOYSA-N
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Compound 77
Molecular Weight:227.687
Molecular Formula:C11H14ClNO2
InChIKey:UXYVAZTWLJBBRL-UHFFFAOYSA-N
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Compound 78
Molecular Weight:207.2689
Molecular Formula:C12H17NO2
InChIKey:BNZLUVRRQMBWEK-UHFFFAOYSA-N
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Compound 79
Molecular Weight:225.671
Molecular Formula:C11H12ClNO2
InChIKey:ADAUJIDSUOTARD-UHFFFAOYSA-N
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Compound 80a
Molecular Weight:587.3982
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 80b
Molecular Weight:623.3791
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 80c
Molecular Weight:615.4513
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 81a
Molecular Weight:469.3101
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 81b
Molecular Weight:505.2911
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 81c
Molecular Weight:497.3633
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 82
Molecular Weight:60.0983
Molecular Formula:C2H8N2
InChIKey:PIICEJLVQHRZGT-UHFFFAOYSA-N
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Compound 83
Molecular Weight:74.1249
Molecular Formula:C3H10N2
InChIKey:KFIGICHILYTCJF-UHFFFAOYSA-N
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Compound 84
Molecular Weight:88.1515
Molecular Formula:C4H12N2
InChIKey:Not Available
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Compound 85
Molecular Weight:116.2046
Molecular Formula:C6H16N2
InChIKey:DFPGBRPWDZFIPP-UHFFFAOYSA-N
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Compound 86
Molecular Weight:88.1515
Molecular Formula:C4H12N2
InChIKey:DILRJUIACXKSQE-UHFFFAOYSA-N
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Compound 87
Molecular Weight:102.1781
Molecular Formula:C5H14N2
InChIKey:HVOYZOQVDYHUPF-UHFFFAOYSA-N
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Compound 88
Molecular Weight:116.2046
Molecular Formula:C6H16N2
InChIKey:KWYHDKDOAIKMQN-UHFFFAOYSA-N
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Compound 89
Molecular Weight:114.1888
Molecular Formula:C6H14N2
InChIKey:SSJXIUAHEKJCMH-PHDIDXHHSA-N
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Compound 90
Molecular Weight:114.1888
Molecular Formula:C6H14N2
InChIKey:SSJXIUAHEKJCMH-OLQVQODUSA-N
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Compound 91
Molecular Weight:114.1888
Molecular Formula:C6H14N2
InChIKey:SSJXIUAHEKJCMH-LWOQYNTDSA-N
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Compound 92
Molecular Weight:142.2419
Molecular Formula:C8H18N2
InChIKey:JRHPOFJADXHYBR-HTQZYQBOSA-N
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Compound 93
Molecular Weight:170.2951
Molecular Formula:C10H22N2
InChIKey:QQHMNKRUMYTFHL-NXEZZACHSA-N
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Compound 94
Molecular Weight:198.3482
Molecular Formula:C12H26N2
InChIKey:VGPJQHMGHSBWTG-VXGBXAGGSA-N
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  1. 1 - 107