Standard Article

Catalytic Asymmetric Hydrogenation of C[DOUBLE BOND]N Functions

  1. Hans-Ulrich Blaser,
  2. Felix Spindler

Published Online: 15 FEB 2010

DOI: 10.1002/0471264180.or074.01

Organic Reactions

Organic Reactions

How to Cite

Blaser, H.-U. and Spindler, F. 2010. Catalytic Asymmetric Hydrogenation of C[DOUBLE BOND]N Functions. Organic Reactions. 1:1–102.

Author Information

  1. Solvias AG, Basel, CH, Switzerland

Publication History

  1. Published Online: 15 FEB 2010

Chemistry Terms

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Abstract

Chiral amines are important targets for synthetic chemists and attempts to prepare such compounds via enantioselective hydrogenation of an appropriate C[DOUBLE BOND]N function date back to 1941. Originally, only heterogeneous hydrogenation catalysts such as Pt black, Pd/C, or Raney nickel were employed. Remarkable progress has been made since the 1990s and a variety of very selective catalysts are now available for the enantioselective reduction of different types of C[DOUBLE BOND]N functions. The first industrial application was announced in 1996. Despite progress, the enantioselective hydrogenation of prochiral C[DOUBLE BOND]N groups such as imines, oximes, or hydrozones is still a challenge.

This chapter provides a comprehensive overview of the enantioselective hydrogenation and transfer hydrogenation of various C[DOUBLE BOND]N functions using chiral catalysts. Because the net transformation is the same for both types, the results of various substrate types are summarized together. In many cases, different catalyst types are required. For example, if hydrogen is used, the metal must be able to activate the very strong H[BOND]H bonds, In contrast, the activation seems to be more facile for the transfer of donor molecules such as formic acid and Hantzch esters, which form aromatic products. This review covers the literature up to September 2007.

Keywords:

  • Asymmetric hydrogenation;
  • Catalysts;
  • Chiral ligands;
  • Rhodium;
  • Iridium;
  • Ruthenium;
  • Palladium;
  • Titanium;
  • Substrates;
  • Imines;
  • C[DOUBLE BOND]N functions;
  • Reductive amination;
  • Mechanisms;
  • Herbicides;
  • Type 2 diabetes;
  • Antitussive agents

Featured Compounds

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  1. 1 - 250
Compound Information
Molecular Weight:257.3276
Molecular Formula:C16H19NO2
InChIKey:ANKTVFMGWOKNGA-LBPRGKRZSA-N
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Compound Information
Molecular Weight:0
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:213.2502
Molecular Formula:C14H12FN
InChIKey:JWOCAGJLFPSCAZ-LFIBNONCSA-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:175.2701
Molecular Formula:C12H17N
InChIKey:IAFIYTMWMGDDQD-JTQLQIEISA-N
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Compound Information
Molecular Weight:131.1745
Molecular Formula:C9H9N
InChIKey:ITJKAVYNAFEJTH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:227.3016
Molecular Formula:C15H17NO
InChIKey:MSRXKOAPHWUNNM-LBPRGKRZSA-N
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Compound Information
Molecular Weight:288.182
Molecular Formula:C15H14BrN
InChIKey:DYKZWFHKCAXSTP-HNNXBMFYSA-N
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Compound Information
Molecular Weight:526.646
Molecular Formula:C31H30N2O4S
InChIKey:CYDXWPGYXQSJAO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:293.2837
Molecular Formula:C16H14F3NO
InChIKey:CZXBDRQTAFKTOK-RGVLZGJSSA-N
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Compound Information
Molecular Weight:292.3318
Molecular Formula:C18H16N2O2
InChIKey:OOOHRYLFPGOMKQ-INIZCTEOSA-N
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Compound Information
Molecular Weight:189.2967
Molecular Formula:C13H19N
InChIKey:HUGWWKUBECAFGE-WYMLVPIESA-N
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Compound Information
Molecular Weight:339.4281
Molecular Formula:C21H25NO3
InChIKey:JARBGNGKYHJEIK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:355.4275
Molecular Formula:C21H25NO4
InChIKey:AWMJUIQAPHXPRD-QQOXCAACSA-N
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Compound Information
Molecular Weight:241.3282
Molecular Formula:C16H19NO
InChIKey:AWFLVVVPPDRGCE-CYBMUJFWSA-N
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Compound Information
Molecular Weight:211.3022
Molecular Formula:C15H17N
InChIKey:FUMMTNFGMROHPC-CYBMUJFWSA-N
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Compound Information
Molecular Weight:317.224
Molecular Formula:C16H17BrN2
InChIKey:HOEZHPNJXBTKKA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:147.2169
Molecular Formula:C10H13N
InChIKey:QPILYVQSKNWRDD-QMMMGPOBSA-N
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Compound Information
Molecular Weight:346.218
Molecular Formula:C17H16BrNO2
InChIKey:SZQUULRLQRRCSJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:242.3593
Molecular Formula:C16H22N2
InChIKey:XWJGDKJAXXBNJC-HOTGVXAUSA-N
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Compound Information
Molecular Weight:358.4523
Molecular Formula:C24H24NO2
InChIKey:FQXWJRJNDXZYKZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:248.3223
Molecular Formula:C17H16N2
InChIKey:INERHEQVAVQJBO-INIZCTEOSA-N
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Compound Information
Molecular Weight:233.3062
Molecular Formula:C14H19NO2
InChIKey:MVIOZTSBCZNBFR-GFCCVEGCSA-N
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Compound Information
Molecular Weight:255.4717
Molecular Formula:C14H29NOSi
InChIKey:ZZHIVDXNEVWVLO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:225.3288
Molecular Formula:C16H19N
InChIKey:XPRLTIADINMCRY-CQSZACIVSA-N
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Compound Information
Molecular Weight:276.172
Molecular Formula:C14H14BrN
InChIKey:DNEGKEWHRNTRDM-LLVKDONJSA-N
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Compound Information
Molecular Weight:257.3706
Molecular Formula:C17H23NO
InChIKey:NPEVCJZMQGZNET-KRWDZBQOSA-N
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Compound Information
Molecular Weight:223.2268
Molecular Formula:C14H9NO2
InChIKey:YYPMRNQIJSHAEE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:247.3327
Molecular Formula:C15H21NO2
InChIKey:JMDPBIGEKKWQLF-CYBMUJFWSA-N
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Compound Information
Molecular Weight:322.368
Molecular Formula:C16H36BrN
InChIKey:Not Available
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Compound Information
Molecular Weight:290.155
Molecular Formula:C14H12BrNO
InChIKey:BVMDZLBQQXQHBN-ZDUSSCGKSA-N
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Compound Information
Molecular Weight:241.3282
Molecular Formula:C16H19NO
InChIKey:UUERSPCNHLAMES-ZDUSSCGKSA-N
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Compound Information
Molecular Weight:191.2695
Molecular Formula:C12H17NO
InChIKey:BTNFFJCPSPWKFJ-JLHYYAGUSA-N
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Compound Information
Molecular Weight:267.3224
Molecular Formula:C17H17NO2
InChIKey:WGTCMJBJRPKENJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:233.3062
Molecular Formula:C14H19NO2
InChIKey:IIAJULAFFLVAGQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:225.2426
Molecular Formula:C14H11NO2
InChIKey:LDJMJOMCSBGIHO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:235.3236
Molecular Formula:C17H17N
InChIKey:UIVYFEUNUWXYEL-ISLYRVAYSA-N
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Compound Information
Molecular Weight:848.676
Molecular Formula:C29H30Na4O12P2S4
InChIKey:RPDXFRHTMDOECX-GOPWMECQSA-J
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Compound Information
Molecular Weight:309.4452
Molecular Formula:C21H27NO
InChIKey:RZYVEKIXNVEMFB-LSDHQDQOSA-N
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Compound Information
Molecular Weight:227.3446
Molecular Formula:C16H21N
InChIKey:LIKCBRNQUWVRIK-WUKNDPDISA-N
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Compound Information
Molecular Weight:229.254
Molecular Formula:C12H7NO2S
InChIKey:RHJRLNLVQNGQPA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:337.212
Molecular Formula:C15H17BrN2O2
InChIKey:STOZNEMGELQCKG-GFCCVEGCSA-N
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Compound Information
Molecular Weight:420.6731
Molecular Formula:C29H44N2
InChIKey:RNWNFPPCLZJYQH-KTKRTIGZSA-N
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Compound Information
Molecular Weight:321.3368
Molecular Formula:C18H18F3NO
InChIKey:WVSBPGQOVDFIGN-LPYMAVHISA-N
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Compound Information
Molecular Weight:359.4608
Molecular Formula:C24H25NO2
InChIKey:DTMDQGQIAKLKNM-DEOSSOPVSA-N
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Compound Information
Molecular Weight:231.721
Molecular Formula:C14H14ClN
InChIKey:KIXBUVXVGZOEBP-LLVKDONJSA-N
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Compound Information
Molecular Weight:329.4348
Molecular Formula:C23H23NO
InChIKey:YSYQZYVHOYHPDZ-HKOYGPOVSA-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:518.624
Molecular Formula:C29H30N2O5S
InChIKey:UBDDZFJLFUCXSI-GDLZYMKVSA-N
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Compound Information
Molecular Weight:255.3117
Molecular Formula:C16H17NO2
InChIKey:UFKQRFKJIPICMZ-SFQUDFHCSA-N
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Compound Information
Molecular Weight:200.2795
Molecular Formula:C13H16N2
InChIKey:FJPPZKPWCBEAMQ-NSHDSACASA-N
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Compound Information
Molecular Weight:274.156
Molecular Formula:C14H12BrN
InChIKey:CUAMSPSCLWAQOI-LFIBNONCSA-N
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Compound Information
Molecular Weight:480.5599
Molecular Formula:C32H34P2
InChIKey:MDAHANCDXSBKPT-YTTGMZPUSA-N
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Compound Information
Molecular Weight:209.2863
Molecular Formula:C15H15N
InChIKey:UBIUKXSDEQNWBN-DTQAZKPQSA-N
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Compound Information
Molecular Weight:253.3389
Molecular Formula:C17H19NO
InChIKey:JYRSCLWVFAVARY-NBVRZTHBSA-N
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Compound Information
Molecular Weight:239.3123
Molecular Formula:C16H17NO
InChIKey:PAKPZDSHRBJZBM-GHRIWEEISA-N
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Compound Information
Molecular Weight:239.335
Molecular Formula:C15H13NS
InChIKey:SFKYSWWVKDKMII-UHFFFAOYSA-N
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Compound Information
Molecular Weight:341.444
Molecular Formula:C21H27NO3
InChIKey:JBDGBKSMCRWFDO-LJQANCHMSA-N
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Compound Information
Molecular Weight:516.608
Molecular Formula:C29H28N2O5S
InChIKey:UEVPMSJGXPSEBC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:257.3276
Molecular Formula:C16H19NO2
InChIKey:HDPZMBKHVZBDQR-GFCCVEGCSA-N
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Compound Information
Molecular Weight:293.3267
Molecular Formula:C17H18F3N
InChIKey:GDKRNXVCXMRMFR-ZDUSSCGKSA-N
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Compound Information
Molecular Weight:261.747
Molecular Formula:C15H16ClNO
InChIKey:MMEUGOXUZUEXBK-LLVKDONJSA-N
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Compound Information
Molecular Weight:225.374
Molecular Formula:C11H15NS2
InChIKey:BVZUARLEUBPVSF-ZRDIBKRKSA-N
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Compound Information
Molecular Weight:357.4434
Molecular Formula:C21H27NO4
InChIKey:MZMBEDUFQKANOF-KRWDZBQOSA-N
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Compound Information
Molecular Weight:618.075
Molecular Formula:C20H30Cl4Rh2
InChIKey:QNIVKTTWBMFSBR-UHFFFAOYSA-J
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Compound Information
Molecular Weight:232.2977
Molecular Formula:C14H18NO2
InChIKey:NQRVIRQTWBNPBI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:169.307
Molecular Formula:C11H23N
InChIKey:NKPYDKIYCJRIEA-JTQLQIEISA-N
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Compound Information
Molecular Weight:430.6679
Molecular Formula:C30H42N2
InChIKey:QKDQEPWPCSMMCA-GLQWPALVSA-N
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Compound Information
Molecular Weight:180.2038
Molecular Formula:C9H12N2O2
InChIKey:KJUDDWTUIKLRMV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:251.366
Molecular Formula:C18H21N
InChIKey:RQLDCWIIRJZODQ-RDTXWAMCSA-N
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Compound Information
Molecular Weight:241.3282
Molecular Formula:C16H19NO
InChIKey:CEOSXFUWKWRLEP-ZDUSSCGKSA-N
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Compound Information
Molecular Weight:480.576
Molecular Formula:C26H28N2O5S
InChIKey:WZIWMVSIGHSJOQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:229.705
Molecular Formula:C14H12ClN
InChIKey:UFOPIDCFYMPMKU-LFIBNONCSA-N
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Compound Information
Molecular Weight:235.3236
Molecular Formula:C17H17N
InChIKey:DWEMOGBQFALLHL-ISLYRVAYSA-N
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Compound Information
Molecular Weight:261.3609
Molecular Formula:C19H19N
InChIKey:GOOYPHDQKHMZHR-HNNXBMFYSA-N
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Compound Information
Molecular Weight:284.439
Molecular Formula:C19H28N2
InChIKey:BZQYKYFNKCQLFG-GOSISDBHSA-N
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Compound Information
Molecular Weight:161.1574
Molecular Formula:C9H7NO2
InChIKey:PEEMVDRTQBESEN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:68.0072
Molecular Formula:CHNaO2
InChIKey:Not Available
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Compound Information
Molecular Weight:177.1998
Molecular Formula:C10H11NO2
InChIKey:BAVCWASJDJFKPK-SSDOTTSWSA-N
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Compound Information
Molecular Weight:387.514
Molecular Formula:C26H29NO2
InChIKey:MNLJKGAGGILQLD-XMMPIXPASA-N
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Compound Information
Molecular Weight:297.3914
Molecular Formula:C19H23NO2
InChIKey:QMFRUXSSVRREFN-AWEZNQCLSA-N
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Compound Information
Molecular Weight:255.3547
Molecular Formula:C17H21NO
InChIKey:DNGJNFJLEJKBGR-CQSZACIVSA-N
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Compound Information
Molecular Weight:229.3605
Molecular Formula:C16H23N
InChIKey:VWDIKJRKNLNNAO-CVEARBPZSA-N
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Compound Information
Molecular Weight:255.3117
Molecular Formula:C16H17NO2
InChIKey:QMQPYAJIBRFJCA-SFQUDFHCSA-N
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Compound Information
Molecular Weight:290.316
Molecular Formula:C18H14N2O2
InChIKey:VORHKXJENRYGEN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:303.3975
Molecular Formula:C21H21NO
InChIKey:NGEIEPLVXQZBHM-MRXNPFEDSA-N
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Compound Information
Molecular Weight:277.3603
Molecular Formula:C19H19NO
InChIKey:AKHXTFSFLLCYTJ-AWEZNQCLSA-N
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Compound Information
Molecular Weight:286.166
Molecular Formula:C15H12BrN
InChIKey:HUDMLAGFSBBGHB-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:212.2902
Molecular Formula:C14H16N2
InChIKey:LXJWBHIVLXMHDZ-CYBMUJFWSA-N
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Compound Information
Molecular Weight:241.351
Molecular Formula:C15H15NS
InChIKey:ZOKMLSVQAGJLDI-AWEZNQCLSA-N
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Compound Information
Molecular Weight:327.3743
Molecular Formula:C19H21NO4
InChIKey:ICSPURBWGBIZCI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:205.253
Molecular Formula:C12H15NO2
InChIKey:VASUQTGZAPZKFK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:39.9971
Molecular Formula:HNaO
InChIKey:HEMHJVSKTPXQMS-UHFFFAOYSA-M
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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:253.2958
Molecular Formula:C16H15NO2
InChIKey:PLVAQVOWIRYCNA-OAHLLOKOSA-N
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Compound Information
Molecular Weight:211.3022
Molecular Formula:C15H17N
InChIKey:KYJKITQCBFVYDT-OAHLLOKOSA-N
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Compound Information
Molecular Weight:223.3129
Molecular Formula:C16H17N
InChIKey:ISOLWJQDGGMUBI-SAPNQHFASA-N
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Compound Information
Molecular Weight:151.2487
Molecular Formula:C10H17N
InChIKey:DDTBKGVNQHISNO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:276.172
Molecular Formula:C14H14BrN
InChIKey:HNJODLQYNPKWRU-LLVKDONJSA-N
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Compound Information
Molecular Weight:304.139
Molecular Formula:C14H10BrNO2
InChIKey:QLGHJCQTJYUMRQ-CYBMUJFWSA-N
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Compound Information
Molecular Weight:243.299
Molecular Formula:C14H10FNS
InChIKey:RKDPYJHQLWJRGW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:225.3089
Molecular Formula:C15H17N2
InChIKey:WCJSIHHWFYNIQC-UHFFFAOYSA-O
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Compound Information
Molecular Weight:177.286
Molecular Formula:C12H19N
InChIKey:VSTYIEJFRYCKGB-NSHDSACASA-N
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Compound Information
Molecular Weight:241.2851
Molecular Formula:C15H15NO2
InChIKey:SOQABZLNGOWFAF-AWEZNQCLSA-N
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Compound Information
Molecular Weight:240.3434
Molecular Formula:C16H20N2
InChIKey:TXMQWIYUVYXDEL-FBMGVBCBSA-N
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Compound Information
Molecular Weight:245.3599
Molecular Formula:C16H23NO
InChIKey:MYZPOXWXMVYFEZ-GHRIWEEISA-N
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Compound Information
Molecular Weight:73.891
Molecular Formula:CLi2O3
InChIKey:XGZVUEUWXADBQD-UHFFFAOYSA-L
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Compound Information
Molecular Weight:288.139
Molecular Formula:C14H10BrNO
InChIKey:BIGPWBHTBWXPEA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:161.2435
Molecular Formula:C11H15N
InChIKey:FTUSZADPSPPGFA-ONGXEEELSA-N
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Compound Information
Molecular Weight:191.3125
Molecular Formula:C13H21N
InChIKey:HPYBESIVESNUBV-LBPRGKRZSA-N
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Compound Information
Molecular Weight:246.3065
Molecular Formula:C17H14N2
InChIKey:LDMKQGDSXJEJHC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:245.315
Molecular Formula:C14H12FNS
InChIKey:MUJIPJXXXWCCTG-ZDUSSCGKSA-N
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Compound Information
Molecular Weight:166.0028
Molecular Formula:IK
InChIKey:NLKNQRATVPKPDG-UHFFFAOYSA-M
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Compound Information
Molecular Weight:369.3682
Molecular Formula:C16H36IN
InChIKey:DPKBAXPHAYBPRL-UHFFFAOYSA-M
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Compound Information
Molecular Weight:226.3168
Molecular Formula:C15H18N2
InChIKey:PQDRDXZZTDQDDF-AWEZNQCLSA-N
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Compound Information
Molecular Weight:117.1479
Molecular Formula:C8H7N
InChIKey:GLWWLZNPPPOICI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:245.292
Molecular Formula:C15H16FNO
InChIKey:LHOLKQFAXYTWHD-NSHDSACASA-N
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Compound Information
Molecular Weight:198.2637
Molecular Formula:C13H14N2
InChIKey:RHZNBRTZMBDFOB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:221.2955
Molecular Formula:C13H19NO2
InChIKey:HEZZOBOIXZUSIY-NSHDSACASA-N
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Compound Information
Molecular Weight:251.366
Molecular Formula:C18H21N
InChIKey:ZZUGFYPGUXESIW-RDTXWAMCSA-N
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Compound Information
Molecular Weight:201.2643
Molecular Formula:C13H15NO
InChIKey:ONDWKYOQPPRERD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:274.156
Molecular Formula:C14H12BrN
InChIKey:GWVSMBGSVIIUKI-LFIBNONCSA-N
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Compound Information
Molecular Weight:259.388
Molecular Formula:C11H17NO2S2
InChIKey:QNRAZCVKFAQJMT-JTQLQIEISA-N
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Compound Information
Molecular Weight:211.3022
Molecular Formula:C15H17N
InChIKey:HFCVXWGJZKTSQX-CYBMUJFWSA-N
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Compound Information
Molecular Weight:275.3874
Molecular Formula:C20H21N
InChIKey:FYQKVCGNZBCIPG-QZQOTICOSA-N
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Compound Information
Molecular Weight:329.3902
Molecular Formula:C19H23NO4
InChIKey:GFMUOHMXSGNQTF-IBGZPJMESA-N
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Compound Information
Molecular Weight:231.721
Molecular Formula:C14H14ClN
InChIKey:MSQDWJPOZCOICB-LLVKDONJSA-N
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Compound Information
Molecular Weight:225.3288
Molecular Formula:C16H19N
InChIKey:XXPOATHRRKDYBT-AWEZNQCLSA-N
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Compound Information
Molecular Weight:185.2649
Molecular Formula:C13H15N
InChIKey:KXAVXNWSOPHOON-UHFFFAOYSA-N
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Compound Information
Molecular Weight:247.3343
Molecular Formula:C18H17N
InChIKey:QVLUYXIDTFCFQJ-CQSZACIVSA-N
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Compound Information
Molecular Weight:331.4507
Molecular Formula:C23H25NO
InChIKey:PLNJQIKHYMJJDS-GOSISDBHSA-N
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Compound Information
Molecular Weight:289.371
Molecular Formula:C20H19NO
InChIKey:QVDNLBMDFIERRC-RCCKNPSSSA-N
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Compound Information
Molecular Weight:139.238
Molecular Formula:C9H17N
InChIKey:QDSNPRFDQJTGGU-CSKARUKUSA-N
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Compound Information
Molecular Weight:223.3129
Molecular Formula:C16H17N
InChIKey:BBRKIWREBVHSMK-SAPNQHFASA-N
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Compound Information
Molecular Weight:482.592
Molecular Formula:C26H30N2O5S
InChIKey:DELGHDTUBKFAQK-AREMUKBSSA-N
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Compound Information
Molecular Weight:151.2487
Molecular Formula:C10H17N
InChIKey:GEQIGSOKBWEGFE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:195.3443
Molecular Formula:C13H25N
InChIKey:CLMZOPCZNHVUOB-DHCBQETCSA-N
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Compound Information
Molecular Weight:159.2276
Molecular Formula:C11H13N
InChIKey:FLHJIAFUWHPJRT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:147.1308
Molecular Formula:C8H5NO2
InChIKey:XKJCHHZQLQNZHY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:479.5663
Molecular Formula:C31H29NO4
InChIKey:VDNBOMRPCRLXKH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:408.6624
Molecular Formula:C28H44N2
InChIKey:IGMAWWQDCMLATL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:255.3547
Molecular Formula:C17H21NO
InChIKey:IYZRINJHKVQAQC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:274.156
Molecular Formula:C14H12BrN
InChIKey:TYORFOGRZSXPPZ-LFIBNONCSA-N
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Compound Information
Molecular Weight:291.3108
Molecular Formula:C17H16F3N
InChIKey:IJJRHLYOLDMWIM-FYJGNVAPSA-N
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Compound Information
Molecular Weight:276.172
Molecular Formula:C14H14BrN
InChIKey:XBAYGDUZTFAECB-LLVKDONJSA-N
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Compound Information
Molecular Weight:304.205
Molecular Formula:C14H10BrNS
InChIKey:APQFMGFLOSZLSR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:221.297
Molecular Formula:C16H15N
InChIKey:LNVBTQNUZBSTMY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:209.2863
Molecular Formula:C15H15N
InChIKey:JATCPLSBWDXCNE-DTQAZKPQSA-N
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Compound Information
Molecular Weight:193.3284
Molecular Formula:C13H23N
InChIKey:IVEMFEAAKYGKBA-ARJAWSKDSA-N
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Compound Information
Molecular Weight:306.221
Molecular Formula:C14H12BrNS
InChIKey:TXRVIYZWIUIDGU-ZDUSSCGKSA-N
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Compound Information
Molecular Weight:211.2591
Molecular Formula:C14H13NO
InChIKey:BKQRBYFLQYHTCV-ZDUSSCGKSA-N
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Compound Information
Molecular Weight:239.3123
Molecular Formula:C16H17NO
InChIKey:CIJFQPNWXIJBTL-GHRIWEEISA-N
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Compound Information
Molecular Weight:131.1745
Molecular Formula:C9H9N
InChIKey:VHPZCMKWBDZWET-UHFFFAOYSA-N
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Compound Information
Molecular Weight:428.652
Molecular Formula:C30H40N2
InChIKey:CIVLKAAOEIPPJU-DOFZRALJSA-N
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Compound Information
Molecular Weight:153.2646
Molecular Formula:C10H19N
InChIKey:YVGKHWNTKNOUHS-SNVBAGLBSA-N
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Compound Information
Molecular Weight:224.3009
Molecular Formula:C15H16N2
InChIKey:SNQCTFSKTODBCD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:201.2643
Molecular Formula:C13H15NO
InChIKey:MVUROKMDHJEIHM-NSHDSACASA-N
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Compound Information
Molecular Weight:319.239
Molecular Formula:C16H19BrN2
InChIKey:UCPVQKIECQFIDV-CQSZACIVSA-N
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Compound Information
Molecular Weight:153.2646
Molecular Formula:C10H19N
InChIKey:IRBCXYVCZZHONL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:185.2649
Molecular Formula:C13H15N
InChIKey:GMZLALYCWQSOQS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:133.1903
Molecular Formula:C9H11N
InChIKey:QSWIJMBKYBFKHA-SECBINFHSA-N
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Compound Information
Molecular Weight:238.3275
Molecular Formula:C16H18N2
InChIKey:GSNYICYKGRDFSN-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:205.2961
Molecular Formula:C13H19NO
InChIKey:YRUUSCWNSWFUAF-KAMYIIQDSA-N
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Compound Information
Molecular Weight:161.1756
Molecular Formula:C10H8FN
InChIKey:GPIARMSVZOEZCV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:275.3444
Molecular Formula:C19H17NO
InChIKey:ZNESLCAPFYHXDK-XSFVSMFZSA-N
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Compound Information
Molecular Weight:422.6889
Molecular Formula:C29H46N2
InChIKey:IHDCSUUGAWHYFT-YLUWWHAYSA-N
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Compound Information
Molecular Weight:163.1733
Molecular Formula:C9H9NO2
InChIKey:QKXXBIFQENFWPM-ZCFIWIBFSA-N
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Compound Information
Molecular Weight:305.4134
Molecular Formula:C21H23NO
InChIKey:PPMTZMZTIZLPBM-MRXNPFEDSA-N
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Compound Information
Molecular Weight:127.91241
Molecular Formula:HI
InChIKey:XMBWDFGMSWQBCA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:225.2857
Molecular Formula:C15H15NO
InChIKey:LBZGHKVTRNVOHW-AWEZNQCLSA-N
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Compound Information
Molecular Weight:245.747
Molecular Formula:C15H16ClN
InChIKey:OQLCAYPQNQXBKW-LBPRGKRZSA-N
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Compound Information
Molecular Weight:183.2475
Molecular Formula:C10H17NO2
InChIKey:ZNMBARZCWNCVLK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:170.593
Molecular Formula:C8H7ClO2
InChIKey:Not Available
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Compound Information
Molecular Weight:197.297
Molecular Formula:C10H15NOS
InChIKey:NMEHPKOPJITPAU-DHZHZOJOSA-N
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Compound Information
Molecular Weight:303.421
Molecular Formula:C20H17NS
InChIKey:RSPMKAUJYFOURJ-IBGZPJMESA-N
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Compound Information
Molecular Weight:239.3123
Molecular Formula:C16H17NO
InChIKey:ADFZIWZTMWRSCS-GHRIWEEISA-N
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Compound Information
Molecular Weight:339.385
Molecular Formula:C20H21NO4
InChIKey:SNBUPJCXGUWBSJ-AWEZNQCLSA-N
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Compound Information
Molecular Weight:225.2857
Molecular Formula:C15H15NO
InChIKey:YXIIXSXZNDIDFR-FOWTUZBSSA-N
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Compound Information
Molecular Weight:239.3123
Molecular Formula:C16H17NO
InChIKey:UARBPQWSTBGKGB-GHRIWEEISA-N
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Compound Information
Molecular Weight:175.2701
Molecular Formula:C12H17N
InChIKey:QFRVVKIFIHGQCH-LBPRGKRZSA-N
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Compound Information
Molecular Weight:114.0596
Molecular Formula:C3H2N2O3
InChIKey:ZFLIKDUSUDBGCD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:250.2952
Molecular Formula:C16H14N2O
InChIKey:AZVIJXJYNSUGLF-LDADJPATSA-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:78.1118
Molecular Formula:C6H6
InChIKey:UHOVQNZJYSORNB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:265.3926
Molecular Formula:C19H23N
InChIKey:JSXHJZYJCPSDSZ-OALUTQOASA-N
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Compound Information
Molecular Weight:119.1638
Molecular Formula:C8H9N
InChIKey:GBIKLFWSUVVUKT-MRVPVSSYSA-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:263.3752
Molecular Formula:C16H25NO2
InChIKey:HEXJYLSBFSMHSC-CQSZACIVSA-N
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Compound Information
Molecular Weight:313.3908
Molecular Formula:C19H23NO3
InChIKey:YQTZICLOPZEECN-QGZVFWFLSA-N
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Compound Information
Molecular Weight:209.2863
Molecular Formula:C15H15N
InChIKey:LXNANOANXPSIOZ-FOCLMDBBSA-N
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Compound Information
Molecular Weight:145.201
Molecular Formula:C10H11N
InChIKey:PQZAWZGYOZRUFT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:74.1216
Molecular Formula:C4H10O
InChIKey:DKGAVHZHDRPRBM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:215.3339
Molecular Formula:C15H21N
InChIKey:AMIHDJXPWWQWRB-DTQAZKPQSA-N
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Compound Information
Molecular Weight:311.3749
Molecular Formula:C19H21NO3
InChIKey:VTZRLTPYHOHQJV-XSFVSMFZSA-N
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Compound Information
Molecular Weight:293.2837
Molecular Formula:C16H14F3NO
InChIKey:NFFJBPZOQXLZAQ-RGVLZGJSSA-N
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Compound Information
Molecular Weight:277.383
Molecular Formula:C18H15NS
InChIKey:JDNRDLBQBZQBQD-KRWDZBQOSA-N
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Compound Information
Molecular Weight:252.311
Molecular Formula:C16H16N2O
InChIKey:GIZLUFDOTHUPOM-LBPRGKRZSA-N
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Compound Information
Molecular Weight:203.2371
Molecular Formula:C12H13NO2
InChIKey:VBMZFACBWDZUSM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:267.3654
Molecular Formula:C18H21NO
InChIKey:AQWPVYPNMOXBEK-XDJHFCHBSA-N
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Compound Information
Molecular Weight:257.4875
Molecular Formula:C14H31NOSi
InChIKey:IACQZNTWAXACGX-CYBMUJFWSA-N
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Compound Information
Molecular Weight:322.584
Molecular Formula:C14H9BrClNO
InChIKey:PMTXFVMYQVXLTH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:161.2435
Molecular Formula:C11H15N
InChIKey:IHEQGRQCHGIUQE-VIFPVBQESA-N
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Compound Information
Molecular Weight:205.2545
Molecular Formula:C15H11N
InChIKey:LPCWDYWZIWDTCV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:301.405
Molecular Formula:C20H15NS
InChIKey:VFWHSXJQZSFIOG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:253.3389
Molecular Formula:C17H19NO
InChIKey:PZWUTFPFWTWPMP-QGZVFWFLSA-N
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Compound Information
Molecular Weight:185.1707
Molecular Formula:C9H9F2NO
InChIKey:BVHSAZFNVBBGNX-YFKPBYRVSA-N
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Compound Information
Molecular Weight:257.3276
Molecular Formula:C16H19NO2
InChIKey:QKMAGJZZEDZKCJ-LBPRGKRZSA-N
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Compound Information
Molecular Weight:306.221
Molecular Formula:C14H12BrNS
InChIKey:CLYLZUZRPJTRNQ-ZDUSSCGKSA-N
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Compound Information
Molecular Weight:333.2715
Molecular Formula:C16H13F6N
InChIKey:NHXAVQASYGVNDG-SNVBAGLBSA-N
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Compound Information
Molecular Weight:183.1548
Molecular Formula:C9H7F2NO
InChIKey:BLQUEQUJBDELIP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:153.2646
Molecular Formula:C10H19N
InChIKey:MPLZTNKPWYFMAL-SNVBAGLBSA-N
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Compound Information
Molecular Weight:171.2383
Molecular Formula:C12H13N
InChIKey:KHSYYLCXQKCYQX-SECBINFHSA-N
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Compound Information
Molecular Weight:285.3377
Molecular Formula:C17H19NO3
InChIKey:WSCZCLNYZHDCJW-LDADJPATSA-N
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Compound Information
Molecular Weight:217.2637
Molecular Formula:C13H15NO2
InChIKey:BWLHJMMILQSMAZ-LBPRGKRZSA-N
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Compound Information
Molecular Weight:257.672
Molecular Formula:C14H8ClNO2
InChIKey:IXIWXAORIJQRHB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:212.2902
Molecular Formula:C14H16N2
InChIKey:IERQAAXIMXMTLX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:355.4275
Molecular Formula:C21H25NO4
InChIKey:HMBAIFXFCAVTSP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:267.3654
Molecular Formula:C18H21NO
InChIKey:BRICEIDMZCPEDF-HTXNQAPBSA-N
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Compound Information
Molecular Weight:143.1852
Molecular Formula:C10H9N
InChIKey:PBYMYAJONQZORL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:275.3444
Molecular Formula:C19H17NO
InChIKey:RFKFWDZCENPYDC-XSFVSMFZSA-N
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Compound Information
Molecular Weight:304.205
Molecular Formula:C14H10BrNS
InChIKey:ABUIRQMJZYTVSZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:353.4116
Molecular Formula:C21H23NO4
InChIKey:KNLCJBRWXVRYRS-FNORWQNLSA-N
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Compound Information
Molecular Weight:267.3654
Molecular Formula:C18H21NO
InChIKey:RZTPARAMIQSLKS-XDJHFCHBSA-N
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Compound Information
Molecular Weight:303.3975
Molecular Formula:C21H21NO
InChIKey:ZNNOTMDEURJLAY-CJLVFECKSA-N
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Compound Information
Molecular Weight:214.3061
Molecular Formula:C14H18N2
InChIKey:BBOAWHADGQBLBD-CYBMUJFWSA-N
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Compound Information
Molecular Weight:589.6938
Molecular Formula:BiI3
InChIKey:KOECRLKKXSXCPB-UHFFFAOYSA-K
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Compound Information
Molecular Weight:223.3129
Molecular Formula:C16H17N
InChIKey:HRVCQTUAMGZRRU-SAPNQHFASA-N
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Compound Information
Molecular Weight:359.4162
Molecular Formula:C20H25NO5
InChIKey:UGOVBXCSQHMXPG-LJQANCHMSA-N
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Compound Information
Molecular Weight:239.3123
Molecular Formula:C16H17NO
InChIKey:FAJTVANROHKGST-WUKNDPDISA-N
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Compound Information
Molecular Weight:144.1732
Molecular Formula:C9H8N2
InChIKey:ALHUXMDEZNLFTA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:229.705
Molecular Formula:C14H12ClN
InChIKey:JDRBRFHFBFAASB-LFIBNONCSA-N
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Compound Information
Molecular Weight:241.3282
Molecular Formula:C16H19NO
InChIKey:PIJHHFWQTLZEJT-ZDUSSCGKSA-N
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Compound Information
Molecular Weight:259.345
Molecular Formula:C19H17N
InChIKey:WWVVACFPNBLRLN-HMMYKYKNSA-N
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Compound Information
Molecular Weight:159.2276
Molecular Formula:C11H13N
InChIKey:XEJFZEYFXUTFPM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:1022.373
Molecular Formula:C38H23BF24N2O3
InChIKey:QDSVFCUSPNKHNR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:253.3389
Molecular Formula:C17H19NO
InChIKey:BDYIOZVNAZVNST-NBVRZTHBSA-N
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Compound Information
Molecular Weight:275.368
Molecular Formula:C18H13NS
InChIKey:PJJQJRGKSWWRBI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:214.3061
Molecular Formula:C14H18N2
InChIKey:ANFOWSMYMVVVLD-ZDUSSCGKSA-N
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Compound Information
Molecular Weight:101.19
Molecular Formula:C6H15N
InChIKey:ZMANZCXQSJIPKH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:175.2701
Molecular Formula:C12H17N
InChIKey:KCDHXVZFQTUJJC-ACCUITESSA-N
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Compound Information
Molecular Weight:217.3498
Molecular Formula:C15H23N
InChIKey:ZELRXKQRIZFQIP-AWEZNQCLSA-N
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Compound Information
Molecular Weight:227.3016
Molecular Formula:C15H17NO
InChIKey:QSEJXHGBIMKOLT-GFCCVEGCSA-N
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Compound Information
Molecular Weight:41.0519
Molecular Formula:C2H3N
InChIKey:WEVYAHXRMPXWCK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:165.2074
Molecular Formula:C10H12FN
InChIKey:BDCCXYVTXRUGAN-ZETCQYMHSA-N
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Compound Information
Molecular Weight:107.1531
Molecular Formula:C7H9N
InChIKey:WGQKYBSKWIADBV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:224.3009
Molecular Formula:C15H16N2
InChIKey:WRDSJOCZQDJYRU-HNNXBMFYSA-N
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Compound Information
Molecular Weight:207.3119
Molecular Formula:C13H21NO
InChIKey:YXWIRQHVEQIJOV-NSHDSACASA-N
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Compound Information
Molecular Weight:287.3551
Molecular Formula:C20H17NO
InChIKey:NBYZSIWWKURRHE-IBGZPJMESA-N
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