Standard Article

Hydrazoic Acid

  1. Gary W. Breton1,
  2. Paul J. Kropp1,
  3. Klaus Banert2

Published Online: 16 SEP 2013

DOI: 10.1002/047084289X.rh029.pub2

e-EROS Encyclopedia of Reagents for Organic Synthesis

e-EROS Encyclopedia of Reagents for Organic Synthesis

How to Cite

Breton, G. W., Kropp, P. J. and Banert, K. 2013. Hydrazoic Acid. e-EROS Encyclopedia of Reagents for Organic Synthesis. .

Author Information

  1. 1

    University of North Carolina, Chapel Hill, NC, USA

  2. 2

    Chemnitz University of Technolog, Chemnitz, Germany

Publication History

  1. Published Online: 16 SEP 2013

Chemistry Terms

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Abstract

original image

 [7782-79-8] HN3 (MW 43.04)

InChI = 1S/HN3/c1-3-2/h1H

(adds electrophilically to alkenes, alkynes, and related conjugated systems,1c and nucleophilically to retenes64 and other electron-poor π-systems65, 70 converts carboxylic acids to amines (Schmidt reaction)1 and alcohols to azides;11a,102 cleaves epoxides;17, 94 aminates arenes;19, 113 affords sulfoximines from sulfoxides;21c reacts with a variety of other functional groups1a such as aldehydes83 or diazo compounds70)

Solubility: sol halogenated hydrocarbons, Et2O, C6H6.

Preparative Methods: treatment of Sodium Azide with Sulfuric Acid, Polyphosphoric Acid;1a,2, 3 or Actic acid33; hydrolysis of Azidotrimethylsilane.4, 34

Handling, Storage, and Precautions: highly toxic; extremely explosive30, 32; use in a fume hood.

Featured Compounds

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  1. 1 - 143
Compound Information
Molecular Weight:144.213
Molecular Formula:C11H12
InChIKey:LXSJYXCAGFFKOR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:188.2472
Molecular Formula:C11H13N3
InChIKey:Not Available
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Compound Information
Molecular Weight:44.0342
Molecular Formula:HN3
InChIKey:Not Available
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Compound Information
Molecular Weight:170.3241
Molecular Formula:C9H18OSi
InChIKey:SBEMOANGDSSPJY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:213.3522
Molecular Formula:C9H19N3OSi
InChIKey:YFHHBCWYZFYUJL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:43.028
Molecular Formula:HN3
InChIKey:JUINSXZKUKVTMD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:84.933
Molecular Formula:CH2Cl2
InChIKey:YMWUJEATGCHHMB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:100.1589
Molecular Formula:C6H12O
InChIKey:Not Available
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Compound Information
Molecular Weight:143.1869
Molecular Formula:C6H13N3O
InChIKey:CLAPUPFXENIQDG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:158.2396
Molecular Formula:C12H14
InChIKey:WCMSFBRREKZZFL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:201.2676
Molecular Formula:C12H15N3
InChIKey:URDOPVIVMKFFHV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:189.679
Molecular Formula:Cl4Ti
InChIKey:Not Available
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Compound Information
Molecular Weight:96.1702
Molecular Formula:C7H12
InChIKey:CTMHWPIWNRWQEG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:139.1982
Molecular Formula:C7H13N3
InChIKey:UTETZECQGJWAQJ-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:123.1558
Molecular Formula:C6H9N3
InChIKey:KKAWZKUTSDQAJT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:115.2092
Molecular Formula:C3H9N3Si
InChIKey:SEDZOYHHAIAQIW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:96.106
Molecular Formula:CH4O3S
InChIKey:AFVFQIVMOAPDHO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:60.0843
Molecular Formula:O2Si
InChIKey:VYPSYNLAJGMNEJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:150.077
Molecular Formula:CHF3O3S
InChIKey:ITMCEJHCFYSIIV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:98.143
Molecular Formula:C6H10O
InChIKey:SHOJXDKTYKFBRD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:141.171
Molecular Formula:C6H11N3O
InChIKey:FRNHBCDOMRJSBQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:60.052
Molecular Formula:C2H4O2
InChIKey:QTBSBXVTEAMEQO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:297.3484
Molecular Formula:C18H19NO3
InChIKey:DXHQHIYAKQFNGV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:268.3535
Molecular Formula:C17H20N2O
InChIKey:UODBZDIYCULNQP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:65.0099
Molecular Formula:N3Na
InChIKey:PXIPVTKHYLBLMZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:98.078
Molecular Formula:H2O4S
InChIKey:QAOWNCQODCNURD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:119.378
Molecular Formula:CHCl3
InChIKey:HEDRZPFGACZZDS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:98.143
Molecular Formula:C6H10O
InChIKey:Not Available
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Compound Information
Molecular Weight:113.1576
Molecular Formula:C6H11NO
InChIKey:JBKVHLHDHHXQEQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:138.1704
Molecular Formula:C6H10N4
InChIKey:CWRVKFFCRWGWCS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:46.0684
Molecular Formula:C2H6O
InChIKey:LFQSCWFLJHTTHZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:141.2108
Molecular Formula:C8H15NO
InChIKey:WZJYOZNDBRCFFG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:182.2179
Molecular Formula:C13H10O
InChIKey:AFMVESZOYKHDBJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:207.2307
Molecular Formula:C13H9N3
InChIKey:POJUGTQVVISLBM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:163.387
Molecular Formula:C2HCl3O2
InChIKey:YNJBWRMUSHSURL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:114.1855
Molecular Formula:C7H14O
InChIKey:RVHXDRXNRJQLGG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:139.1982
Molecular Formula:C7H13N3
InChIKey:MCLCYZAQJQIVAO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:152.214
Molecular Formula:C8H8OS
InChIKey:GRZBTDFINXUJGL-LURJTMIESA-N
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Compound Information
Molecular Weight:177.226
Molecular Formula:C8H7N3S
InChIKey:XPYBFHUSIUMKMJ-ZCFIWIBFSA-N
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Compound Information
Molecular Weight:262.2855
Molecular Formula:C18H15P
InChIKey:RIOQSEWOXXDEQQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:174.1546
Molecular Formula:C6H10N2O4
InChIKey:FAMRKDQNMBBFBR-BQYQJAHWSA-N
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Compound Information
Molecular Weight:92.1384
Molecular Formula:C7H8
InChIKey:YXFVVABEGXRONW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:188.1779
Molecular Formula:C8H12O5
InChIKey:LDFQMMUIJQDSAB-PHDIDXHHSA-N
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Compound Information
Molecular Weight:231.2059
Molecular Formula:C8H13N3O5
InChIKey:PAYWEEWLNCAURI-NTSWFWBYSA-N
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Compound Information
Molecular Weight:73.0938
Molecular Formula:C3H7NO
InChIKey:ZMXDDKWLCZADIW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:112.1696
Molecular Formula:C7H12O
InChIKey:FIEKVYPYFQSFTP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:155.1976
Molecular Formula:C7H13N3O
InChIKey:XNNJMTWCMITJHV-RNFRBKRXSA-N
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Compound Information
Molecular Weight:114.1648
Molecular Formula:C6H15Al
InChIKey:VOITXYVAKOUIBA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:156.2237
Molecular Formula:C12H12
InChIKey:RJTJVVYSTUQWNI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:197.2358
Molecular Formula:C12H11N3
InChIKey:OYDIIQABGXOBJL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:227.004
Molecular Formula:C8Cl2N2O2
InChIKey:HZNVUJQVZSTENZ-UHFFFAOYSA-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:93.148
Molecular Formula:C2H7NOS
InChIKey:DTGSFFWQUULHIF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:328.214
Molecular Formula:C14H11Cl2NO2S
InChIKey:ZTHLGLGSXYHZSS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:290.768
Molecular Formula:C14H11ClN2OS
InChIKey:ZSRNZJWOCVGNQX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:119.1207
Molecular Formula:C7H5NO
InChIKey:Not Available
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Compound Information
Molecular Weight:162.1487
Molecular Formula:C7H6N4O
InChIKey:NKWZCQUWZZTPRH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:135.186
Molecular Formula:C7H5NS
InChIKey:QKFJKGMPGYROCL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:178.214
Molecular Formula:C7H6N4S
InChIKey:WBIAWXNTQCZGMO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:36.461
Molecular Formula:ClH
InChIKey:VEXZGXHMUGYJMC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:26.0174
Molecular Formula:CHN
InChIKey:XFXPMWWXUTWYJX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:70.0534
Molecular Formula:CH2N4
InChIKey:DFRRALWXTFSAEC-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:55.0785
Molecular Formula:C3H5N
InChIKey:Not Available
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Compound Information
Molecular Weight:98.1065
Molecular Formula:C3H6N4
InChIKey:PZDFYVBXRWSAON-UHFFFAOYSA-N
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Compound Information
Molecular Weight:74.1216
Molecular Formula:C4H10O
InChIKey:RTZKZFJDLAIYFH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:233.2631
Molecular Formula:C13H15NO3
InChIKey:BYRDCEJWPFPSKB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:276.2911
Molecular Formula:C13H16N4O3
InChIKey:GWYBQNUIQGUNEI-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:134.1751
Molecular Formula:C9H10O
InChIKey:SIZDIMDMQQFWLM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:121.1796
Molecular Formula:C8H11N
InChIKey:RQEUFEKYXDPUSK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:114.0233
Molecular Formula:C2HF3O2
InChIKey:DTQVDTLACAAQTR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:37.954
Molecular Formula:AlH4Li
InChIKey:OCZDCIYGECBNKL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:103.1213
Molecular Formula:C7H5N
InChIKey:JFDZBHWFFUWGJE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:146.1493
Molecular Formula:C7H6N4
InChIKey:MARUHZGHZWCEQU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:99.1311
Molecular Formula:C5H9NO
InChIKey:SECXISVLQFMRJM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:18.0153
Molecular Formula:H2O
InChIKey:XLYOFNOQVPJJNP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:205.253
Molecular Formula:C12H15NO2
InChIKey:AKFIXTAIQHJWAU-NWDGAFQWSA-N
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Compound Information
Molecular Weight:248.281
Molecular Formula:C12H16N4O2
InChIKey:AQZJXHLBOANADE-RYUDHWBXSA-N
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Compound Information
Molecular Weight:92.1384
Molecular Formula:C7H8
InChIKey:SJYNFBVQFBRSIB-KNVOCYPGSA-N
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Compound Information
Molecular Weight:135.1665
Molecular Formula:C7H9N3
InChIKey:CTYUYTLJJKGKND-RRKCRQDMSA-N
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Compound Information
Molecular Weight:217.2637
Molecular Formula:C13H15NO2
InChIKey:UAJRAENOOXFYEQ-CMDGGOBGSA-N
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Compound Information
Molecular Weight:260.2917
Molecular Formula:C13H16N4O2
InChIKey:OBKBXZGMFQJARU-NSHDSACASA-N
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Compound Information
Molecular Weight:260.2917
Molecular Formula:C13H16N4O2
InChIKey:OBKBXZGMFQJARU-LLVKDONJSA-N
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Compound Information
Molecular Weight:586.8263
Molecular Formula:C37H55AlN2O2
InChIKey:DESAYIFUNLKGNY-OHRASPNLSA-L
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Compound Information
Molecular Weight:202.206
Molecular Formula:C12H10O3
InChIKey:YHOYJNAKBOGOCW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:217.2206
Molecular Formula:C12H11NO3
InChIKey:ZDNWEGQTJQYBRD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:108.0948
Molecular Formula:C6H4O2
InChIKey:AZQWKYJCGOJGHM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:151.1228
Molecular Formula:C6H5N3O2
InChIKey:GECUOSUZVAGXEW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:160.2124
Molecular Formula:C11H12O
InChIKey:JOUZMNDVSQYYTG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:207.2689
Molecular Formula:C12H17NO2
InChIKey:FELVLVFBUHQNNO-NSHDSACASA-N
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Compound Information
Molecular Weight:207.2689
Molecular Formula:C12H17NO2
InChIKey:FELVLVFBUHQNNO-LLVKDONJSA-N
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Compound Information
Molecular Weight:321.238
Molecular Formula:C19H23FeN
InChIKey:QQZJKKWEDVMKTP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:54.0474
Molecular Formula:C3H2O
InChIKey:IJNJLGFTSIAHEA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:97.0754
Molecular Formula:C3H3N3O
InChIKey:KTXQUVBNKPDYGE-OWOJBTEDSA-N
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Compound Information
Molecular Weight:97.0754
Molecular Formula:C3H3N3O
InChIKey:MOLKLIYWXFEEJM-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:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:30.026
Molecular Formula:CH2O
InChIKey:Not Available
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Compound Information
Molecular Weight:71.0381
Molecular Formula:CHN3O
InChIKey:XJRPXNWUCVZVJP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:215.555
Molecular Formula:C5H6ClCrNO3
InChIKey:Not Available
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Compound Information
Molecular Weight:58.0361
Molecular Formula:C2H2O2
InChIKey:LEQAOMBKQFMDFZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:227.9406
Molecular Formula:H5IO6
InChIKey:Not Available
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Compound Information
Molecular Weight:116.1583
Molecular Formula:C6H12O2
InChIKey:PFURGBBHAOXLIO-PHDIDXHHSA-N
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Compound Information
Molecular Weight:166.1838
Molecular Formula:C6H10N6
InChIKey:VVOKGDAKFPYWTN-WDSKDSINSA-N
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Compound Information
Molecular Weight:166.1838
Molecular Formula:C6H10N6
InChIKey:VVOKGDAKFPYWTN-OLQVQODUSA-N
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Compound Information
Molecular Weight:72.1057
Molecular Formula:C4H8O
InChIKey:WYURNTSHIVDZCO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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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:192.342
Molecular Formula:C8H16OS2
InChIKey:GKDUXNAYTAXACL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:217.355
Molecular Formula:C8H15N3S2
InChIKey:SYNZNWRFKPIRFX-SFYZADRCSA-N
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Compound Information
Molecular Weight:217.355
Molecular Formula:C8H15N3S2
InChIKey:SYNZNWRFKPIRFX-YUMQZZPRSA-N
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Compound Information
Molecular Weight:386.5259
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:385.5411
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:202.2078
Molecular Formula:C8H14N2O4
InChIKey:VVWRJUBEIPHGQF-MDZDMXLPSA-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:283.1731
Molecular Formula:C10H7F6N3
InChIKey:LYDPJGVXROAXTN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:373.285
Molecular Formula:C23H17Br
InChIKey:UPPKHJKIUJAIMG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:335.4012
Molecular Formula:C23H17N3
InChIKey:BVJMKGNDUMUPMR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:239.053
Molecular Formula:C8H8Cl2O4
InChIKey:YDPWYNYVGVBHKU-CIIODKQPSA-N
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Compound Information
Molecular Weight:252.1869
Molecular Formula:C8H8N6O4
InChIKey:RVZGXKWALWNZRM-CIIODKQPSA-N
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Compound Information
Molecular Weight:216.231
Molecular Formula:C10H16O5
InChIKey:LTMHNWPUDSTBKD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:185.1772
Molecular Formula:C8H11NO4
InChIKey:RQVJRNFLYNRAEO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:180.2005
Molecular Formula:C10H12O3
InChIKey:RJNVSQLNEALZLC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:180.2005
Molecular Formula:C10H12O3
InChIKey:RJNVSQLNEALZLC-MRVPVSSYSA-N
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Compound Information
Molecular Weight:180.2005
Molecular Formula:C10H12O3
InChIKey:RJNVSQLNEALZLC-QMMMGPOBSA-N
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Compound Information
Molecular Weight:223.2285
Molecular Formula:C10H13N3O3
InChIKey:NUWVUTBUFDNXQO-QMMMGPOBSA-N
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Compound Information
Molecular Weight:1134.9843
Molecular Formula:C42H70O35
InChIKey:WHGYBXFWUBPSRW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:96.1271
Molecular Formula:C6H8O
InChIKey:QLQSJLSVPZCPPZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:164.1679
Molecular Formula:C6H8N6
InChIKey:KPRARVDAEPLFFF-OLQVQODUSA-N
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Compound Information
Molecular Weight:131.1745
Molecular Formula:C9H9N
InChIKey:HYSAJZJNEJKIMJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:174.2025
Molecular Formula:C9H10N4
InChIKey:ZDWCKBBMXCUJRT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:107.1531
Molecular Formula:C7H9N
InChIKey:RNVCVTLRINQCPJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:107.1531
Molecular Formula:C7H9N
InChIKey:JJYPMNFTHPTTDI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:107.1531
Molecular Formula:C7H9N
InChIKey:RZXMPPFPUUCRFN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:320.3865
Molecular Formula:C23H16N2
InChIKey:OHDHTFOFZOPOLQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:335.4012
Molecular Formula:C23H17N3
InChIKey:BVJMKGNDUMUPMR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:235.9238
Molecular Formula:AsF7N2
InChIKey:GBQIOEIWEDLFHN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:258.9455
Molecular Formula:AsF6N5
InChIKey:NUDNXBNRRNVSRH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:20.00634
Molecular Formula:FH
InChIKey:KRHYYFGTRYWZRS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:282.76
Molecular Formula:F7N2Sb
InChIKey:RTCRBFXJLPRVLR-UHFFFAOYSA-H
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Compound Information
Molecular Weight:305.78
Molecular Formula:F6N5Sb
InChIKey:BSTJKZVEXJSDBB-UHFFFAOYSA-H
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