Standard Article

Hydrocyanation of Alkenes and Alkynes

  1. T. V. (Babu) Rajanbabu

Published Online: 16 DEC 2011

DOI: 10.1002/0471264180.or075.01

Organic Reactions

Organic Reactions

How to Cite

Rajanbabu, T. V. 2011. Hydrocyanation of Alkenes and Alkynes. Organic Reactions. 75:1:1–74.

Author Information

  1. The Ohio State University, Department of Chemistry, Columbus, Ohio

Publication History

  1. Published Online: 16 DEC 2011

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Abstract

Hydrogen cyanide is an abundantly available feedstock that is useful for the synthesis of organonitrile intermediates, which serve as precursors for amines, amides, isocyanates, carboxylic acid, and esters. Many of these compounds are used in the manufacture of polymers, agrichemicals, cosmetics, and pharmaceuticals. Hydrogen cyanide itself is relatively unreactive, but in the presence of a catalyst HCN adds to carbonyl compounds, alkenes, and alkynes offering a direct and economical way to such organonitrile intermediates.

This chapter focuses primarily on the metal-catalyzed hydrocyanation of alkenes or alkynes. Acetone cyanohydrin and trimethylsilyl cyanide (TMSCN), both commercially available reagents, can be used for the in-situ generation of HCN. In some transition-metal catalyzed additions, TMSCN acts as a surrogate for HCN, giving products where the TMS group replaces the hydrogen. Preparatively, these reagents provide some advantages since the handling of toxic HCN is avoided. Reactions of these reagents are included here under appropriate substrate and direct comparison of yield and selectivity can be made.

Keywords:

  • Hydrocyanation;
  • Alkenes;
  • Alkynes;
  • Asymmetric hydrocyanation;
  • Metal catalysts;
  • Norbornene;
  • Vinylarenes;
  • 1,3-Dienes;
  • Safety;
  • Hydrogen cyanide;
  • Conjugate addition;
  • Mechanisms;
  • Experimental procedures

Featured Compounds

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  1. 1 - 250
Compound Information
Molecular Weight:1.00794
Molecular Formula:H
InChIKey:GPRLSGONYQIRFK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:235.785
Molecular Formula:C12H14ClNSi
InChIKey:UAFLRUBDUJQNDP-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:156.2221
Molecular Formula:C9H16O2
InChIKey:LXZCLRRLFDLHIG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:209.4032
Molecular Formula:C12H23NSi
InChIKey:XIYUMPPZRLCXRM-QXMHVHEDSA-N
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Compound Information
Molecular Weight:319.6368
Molecular Formula:C5H9NNiY2
InChIKey:CQIOHEFCBFNRKW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:95.1424
Molecular Formula:C6H9N
InChIKey:BJWNKFVWHPJKQZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:53.491
Molecular Formula:ClH4N
InChIKey:NLXLAEXVIDQMFP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:223.2698
Molecular Formula:C15H13NO
InChIKey:KWCOIJCMGJWALT-GFCCVEGCSA-N
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Compound Information
Molecular Weight:154.2078
Molecular Formula:C12H10
InChIKey:Not Available
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Compound Information
Molecular Weight:266.23
Molecular Formula:Br2Pd
InChIKey:INIOZDBICVTGEO-UHFFFAOYSA-L
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Compound Information
Molecular Weight:254.2408
Molecular Formula:C14H10N2O3
InChIKey:HAVPNQPKNQUNJM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:100.1589
Molecular Formula:C6H12O
InChIKey:HFYAEUXHCMTPOL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:154.3247
Molecular Formula:C9H18Si
InChIKey:ZVVPBKWLXJMYSH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:185.2649
Molecular Formula:C13H15N
InChIKey:DHPALHRUPDWYGL-LLVKDONJSA-N
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Compound Information
Molecular Weight:178.3064
Molecular Formula:C9H14N2Si
InChIKey:MYWJLCXWLMYINN-HJWRWDBZSA-N
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Compound Information
Molecular Weight:122.1396
Molecular Formula:C8H7F
InChIKey:JWVTWJNGILGLAT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:95.1424
Molecular Formula:C6H9N
InChIKey:GUMUOYSOENKSEG-ONEGZZNKSA-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:123.1955
Molecular Formula:C8H13N
InChIKey:ABCPPDQWESZYCY-ALCCZGGFSA-N
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Compound Information
Molecular Weight:86.1323
Molecular Formula:C5H10O
InChIKey:HNVRRHSXBLFLIG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:116.1598
Molecular Formula:C9H8
InChIKey:WEHMXWJFCCNXHJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:144.213
Molecular Formula:C11H12
InChIKey:HETLRQLNJZNYFU-JXMROGBWSA-N
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Compound Information
Molecular Weight:309.259
Molecular Formula:C16H19FeNSi
InChIKey:DULDPCSUEFGNSQ-OTBYXNOXSA-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:106.42
Molecular Formula:Pd
InChIKey:KDLHZDBZIXYQEI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:145.201
Molecular Formula:C10H11N
InChIKey:IQIWPLPOZHJNMX-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:68.117
Molecular Formula:C5H8
InChIKey:Not Available
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Compound Information
Molecular Weight:42.0797
Molecular Formula:C3H6
InChIKey:QQONPFPTGQHPMA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:351.4284
Molecular Formula:CNNiY3
InChIKey:ICNMVDPHXCAMMJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:111.1848
Molecular Formula:C7H13N
InChIKey:SDAXRHHPNYTELL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:498.5321
Molecular Formula:C31H32O2P2
InChIKey:VCHDBLPQYJAQSQ-KYJUHHDHSA-N
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Compound Information
Molecular Weight:133.341
Molecular Formula:AlCl3
InChIKey:VSCWAEJMTAWNJL-UHFFFAOYSA-K
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Compound Information
Molecular Weight:84.1595
Molecular Formula:C6H12
InChIKey:LIKMAJRDDDTEIG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:159.2276
Molecular Formula:C11H13N
InChIKey:VIUPTAFHLRBHBO-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:150.2606
Molecular Formula:C11H18
InChIKey:LUKZREJJLWEWQM-YRNVUSSQSA-N
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Compound Information
Molecular Weight:102.1332
Molecular Formula:C8H6
InChIKey:UEXCJVNBTNXOEH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:56.1063
Molecular Formula:C4H8
InChIKey:IAQRGUVFOMOMEM-ONEGZZNKSA-N
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Compound Information
Molecular Weight:130.1864
Molecular Formula:C10H10
InChIKey:IHOYDALOVDQINJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:131.1745
Molecular Formula:C9H9N
InChIKey:ACRWYXSKEHUQDB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:58.6934
Molecular Formula:Ni
InChIKey:PXHVJJICTQNCMI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:521.22
Molecular Formula:C25H23O3SSn
InChIKey:NIXYTNPCKWHSER-UHFFFAOYSA-M
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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:155.1943
Molecular Formula:C8H13NO2
InChIKey:QNBPQJOMXHOTLY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:142.218
Molecular Formula:C8H19Al
InChIKey:AZWXAPCAJCYGIA-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:221.4139
Molecular Formula:C13H23NSi
InChIKey:QKVJQTQXOJXVSZ-JLHYYAGUSA-N
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Compound Information
Molecular Weight:110.1751
Molecular Formula:C7H11N
InChIKey:Not Available
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Compound Information
Molecular Weight:181.3501
Molecular Formula:C10H19NSi
InChIKey:ZMIUGYGUIVEFGY-NTMALXAHSA-N
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Compound Information
Molecular Weight:108.1411
Molecular Formula:C6H8N2
InChIKey:FPPLREPCQJZDAQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:211.3006
Molecular Formula:C12H21NO2
InChIKey:MEJDQSMJRGIWDS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:83.0886
Molecular Formula:C4H5NO
InChIKey:LZJDCFUZEZQGQR-UPHRSURJSA-N
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Compound Information
Molecular Weight:143.45
Molecular Formula:BrCu
InChIKey:NKNDPYCGAZPOFS-UHFFFAOYSA-M
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Compound Information
Molecular Weight:160.2124
Molecular Formula:C11H12O
InChIKey:QMSZFFOZKQBRIB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:109.1689
Molecular Formula:C7H11N
InChIKey:GURORDQYFXXZCY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:89.563
Molecular Formula:CCuN
InChIKey:DULSAGLWMRMKCQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:30.069
Molecular Formula:C2H6
InChIKey:OTMSDBZUPAUEDD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:79.0999
Molecular Formula:C5H5N
InChIKey:VMUWIDHKAIGONP-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:81.1158
Molecular Formula:C5H7N
InChIKey:ISBHMJZRKAFTGE-ONEGZZNKSA-N
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Compound Information
Molecular Weight:154.3247
Molecular Formula:C9H18Si
InChIKey:SFCRJYVNDZSYCT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:158.2396
Molecular Formula:C12H14
InChIKey:HTIZRCMPKFGBAA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:140.2227
Molecular Formula:C9H16O
InChIKey:GVCJLTJIXQROOE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:109.1689
Molecular Formula:C7H11N
InChIKey:UHZMGSZPOTXNPH-ALCCZGGFSA-N
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Compound Information
Molecular Weight:254.2408
Molecular Formula:C14H10N2O3
InChIKey:WDNQAGKUPHNXLE-RMKNXTFCSA-N
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Compound Information
Molecular Weight:177.286
Molecular Formula:C12H19N
InChIKey:ZJGZWTJPMJEPLI-GFCCVEGCSA-N
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Compound Information
Molecular Weight:181.3501
Molecular Formula:C10H19NSi
InChIKey:AOSGVIHTAFDZLE-CMDGGOBGSA-N
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Compound Information
Molecular Weight:289.2848
Molecular Formula:C18H11NO3
InChIKey:UCPICPAXUUJOMB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:125.2437
Molecular Formula:C6H11NSi
InChIKey:IXSXKDMDSFJFPV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:180.2451
Molecular Formula:C14H12
InChIKey:HDBWAWNLGGMZRQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:275.0552
Molecular Formula:C16H24Ni
InChIKey:BLXUJTAYFIWAMG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:95.1424
Molecular Formula:C6H9N
InChIKey:AYDNYRHVOPYCDZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:136.315
Molecular Formula:Cl2Zn
InChIKey:Not Available
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Compound Information
Molecular Weight:187.2808
Molecular Formula:C13H17N
InChIKey:PKQKHWNHCKNYSW-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:207.2704
Molecular Formula:C15H13N
InChIKey:JKTVGIDNYIWPRZ-GFCCVEGCSA-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:18.0153
Molecular Formula:H2O
InChIKey:XLYOFNOQVPJJNP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:242.123
Molecular Formula:C18H15B
InChIKey:MXSVLWZRHLXFKH-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:138.2499
Molecular Formula:C10H18
InChIKey:PJTMQLHFQYFBBB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:96.1702
Molecular Formula:C7H12
InChIKey:FOALCTWKQSWRST-UHFFFAOYSA-N
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Compound Information
Molecular Weight:474.5122
Molecular Formula:C32H28P2
InChIKey:Not Available
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Compound Information
Molecular Weight:167.3235
Molecular Formula:C9H17NSi
InChIKey:VIVVECXOKKBOLU-SOFGYWHQSA-N
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Compound Information
Molecular Weight:134.452
Molecular Formula:Cl2Cu
InChIKey:ORTQZVOHEJQUHG-UHFFFAOYSA-L
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Compound Information
Molecular Weight:122.2075
Molecular Formula:C9H14
InChIKey:YHGPUHUSTRYSIC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:130.1864
Molecular Formula:C10H10
InChIKey:Not Available
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Compound Information
Molecular Weight:191.1834
Molecular Formula:C10H9NO3
InChIKey:VPKYFLUXLQXTTQ-IUIUHRLSSA-N
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Compound Information
Molecular Weight:187.2377
Molecular Formula:C12H13NO
InChIKey:TZJHICIICFHYKK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:230.2592
Molecular Formula:C14H14O3
InChIKey:Not Available
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Compound Information
Molecular Weight:118.1757
Molecular Formula:C9H10
InChIKey:QROGIFZRVHSFLM-QHHAFSJGSA-N
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Compound Information
Molecular Weight:112.2126
Molecular Formula:C8H16
InChIKey:KWKAKUADMBZCLK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:81.1158
Molecular Formula:C5H7N
InChIKey:ISBHMJZRKAFTGE-ONEGZZNKSA-N
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Compound Information
Molecular Weight:240.2142
Molecular Formula:C13H8N2O3
InChIKey:XUGXDMPWORTIDO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:179.2173
Molecular Formula:C13H9N
InChIKey:LDNOHSSUUYPFBW-LLVKDONJSA-N
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Compound Information
Molecular Weight:367.5582
Molecular Formula:C25H25NSi
InChIKey:CCDKVJYMXRYTMG-QURGRASLSA-N
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Compound Information
Molecular Weight:183.2475
Molecular Formula:C10H17NO2
InChIKey:OJHSUJIEKDWRHI-UXBLZVDNSA-N
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Compound Information
Molecular Weight:254.2408
Molecular Formula:C14H10N2O3
InChIKey:IQEFVFLJFODRKT-XNWCZRBMSA-N
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Compound Information
Molecular Weight:137.2221
Molecular Formula:C9H15N
InChIKey:ZDABXXBBEPIUOZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:145.201
Molecular Formula:C10H11N
InChIKey:VELPKXLIEFPYNV-SECBINFHSA-N
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Compound Information
Molecular Weight:113.1971
Molecular Formula:C7H13N
InChIKey:Not Available
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Compound Information
Molecular Weight:211.3006
Molecular Formula:C12H21NO2
InChIKey:YCQVSCKHCCADCQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:136.578
Molecular Formula:C8H5Cl
InChIKey:LFZJRTMTKGYJRS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:184.2753
Molecular Formula:C11H20O2
InChIKey:SBIGSHCJXYGFMX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:137.2221
Molecular Formula:C9H15N
InChIKey:WOVJAWMZNOWDII-BQYQJAHWSA-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:205.2545
Molecular Formula:C15H11N
InChIKey:VFOKYTYWXOYPOX-PTNGSMBKSA-N
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Compound Information
Molecular Weight:109.1689
Molecular Formula:C7H11N
InChIKey:BPRRVWSZQDGBBK-SNAWJCMRSA-N
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Compound Information
Molecular Weight:239.3877
Molecular Formula:C15H17NSi
InChIKey:QNNFNOLYBAYNDQ-SQFISAMPSA-N
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Compound Information
Molecular Weight:129.839
Molecular Formula:Cl2Co
InChIKey:Not Available
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Compound Information
Molecular Weight:201.3397
Molecular Formula:C12H15NSi
InChIKey:AVOFXUGDBQVORW-BENRWUELSA-N
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Compound Information
Molecular Weight:310.2837
Molecular Formula:C18H15O3P
InChIKey:HVLLSGMXQDNUAL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:62.0678
Molecular Formula:C2H6O2
InChIKey:Not Available
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Compound Information
Molecular Weight:181.2331
Molecular Formula:C13H11N
InChIKey:DSFKHFMINARDFV-SNVBAGLBSA-N
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Compound Information
Molecular Weight:120.1237
Molecular Formula:C8H5F
InChIKey:Not Available
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Compound Information
Molecular Weight:238.2796
Molecular Formula:C13H18O4
InChIKey:WTLVSRZNPGZLSM-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:128.169
Molecular Formula:C7H12O2
InChIKey:ASKDFGVMJZMYEM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:136.7467
Molecular Formula:C3N3Ni
InChIKey:IEIIIJMMTWMZSK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:82.1436
Molecular Formula:C6H10
InChIKey:CGHIBGNXEGJPQZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:223.4298
Molecular Formula:C13H25NSi
InChIKey:UFKYYPMZIHJUNW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:243.4194
Molecular Formula:C15H21NSi
InChIKey:QDKPAQZEJZESGN-OWBHPGMISA-N
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Compound Information
Molecular Weight:54.0904
Molecular Formula:C4H6
InChIKey:KAKZBPTYRLMSJV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:139.2703
Molecular Formula:C7H13NSi
InChIKey:FQQPFIMLHOFVRC-VOTSOKGWSA-N
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Compound Information
Molecular Weight:121.1796
Molecular Formula:C8H11N
InChIKey:GAHKEUUHTHVKEA-KVARREAHSA-N
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Compound Information
Molecular Weight:201.3397
Molecular Formula:C12H15NSi
InChIKey:SYFAYDNWAPOSIR-XFXZXTDPSA-N
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Compound Information
Molecular Weight:83.1317
Molecular Formula:C5H9N
InChIKey:RCEJCSULJQNRQQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:199.1724
Molecular Formula:C10H8F3N
InChIKey:AAZNHPRPIMRMMI-SSDOTTSWSA-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:219.3302
Molecular Formula:C12H14FNSi
InChIKey:MYZULEPZHRNXQB-PKNBQFBNSA-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:110.1106
Molecular Formula:C6H6O2
InChIKey:QIGBRXMKCJKVMJ-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:181.3501
Molecular Formula:C10H19NSi
InChIKey:RHEAOHQWKTYATR-CLFYSBASSA-N
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Compound Information
Molecular Weight:198.2355
Molecular Formula:C14H11F
InChIKey:NTYHSGAJVIGSEY-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:139.238
Molecular Formula:C9H17N
InChIKey:PLZZPPHAMDJOSR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:157.2117
Molecular Formula:C11H11N
InChIKey:COUCFFKFRSNZNO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:119.1638
Molecular Formula:C8H9N
InChIKey:BMAXQTDMWYDIJX-KJFJCRTCSA-N
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Compound Information
Molecular Weight:153.2215
Molecular Formula:C9H15NO
InChIKey:DUODJECUNIYWQA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:142.1971
Molecular Formula:C11H10
InChIKey:DREXYQDGEBSCPG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:169.1348
Molecular Formula:C7H7NO4
InChIKey:FODBHLMSMZRICS-HYXAFXHYSA-N
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Compound Information
Molecular Weight:130.1864
Molecular Formula:C10H10
InChIKey:FFFMSANAQQVUJA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:178.2292
Molecular Formula:C14H10
InChIKey:JRXXLCKWQFKACW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:115.601
Molecular Formula:C3H2CuN
InChIKey:YVFWNISGIWLXDP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:106.165
Molecular Formula:C8H10
InChIKey:YNQLUTRBYVCPMQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:123.1955
Molecular Formula:C8H13N
InChIKey:RNURVCLODNWBCS-FNORWQNLSA-N
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Compound Information
Molecular Weight:157.2117
Molecular Formula:C11H11N
InChIKey:QFYUIQMDJGQTGR-JARNTUPDSA-N
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Compound Information
Molecular Weight:108.1411
Molecular Formula:C6H8N2
InChIKey:BTGRAWJCKBQKAO-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:112.245
Molecular Formula:C6H12Si
InChIKey:DCGLONGLPGISNX-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:316.3102
Molecular Formula:C19H12N2O3
InChIKey:ANJNLTXTDXSDBT-GXDHUFHOSA-N
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Compound Information
Molecular Weight:212.2041
Molecular Formula:C12H8N2O2
InChIKey:FGDHHSNLPFIAKD-ONEGZZNKSA-N
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Compound Information
Molecular Weight:98.143
Molecular Formula:C6H10O
InChIKey:QXLPXWSKPNOQLE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:97.1152
Molecular Formula:C5H7NO
InChIKey:YGBHRJCYEZIPDN-GORDUTHDSA-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:171.1937
Molecular Formula:C8H13NO3
InChIKey:IQONNPKPQVPJKT-BAQGIRSFSA-N
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Compound Information
Molecular Weight:121.1796
Molecular Formula:C8H11N
InChIKey:KUCCQBNFRCBJDV-VMPITWQZSA-N
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Compound Information
Molecular Weight:622.6724
Molecular Formula:C44H32P2
InChIKey:Not Available
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Compound Information
Molecular Weight:367.5582
Molecular Formula:C25H25NSi
InChIKey:OAVPILXMMIYOOE-QQTULTPQSA-N
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Compound Information
Molecular Weight:28.0532
Molecular Formula:C2H4
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:340.5329
Molecular Formula:C24H24Si
InChIKey:ZPZWFBVVNHYCFL-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:99.2065
Molecular Formula:C4H9NSi
InChIKey:Not Available
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Compound Information
Molecular Weight:337.4861
Molecular Formula:C17H27NO4Si
InChIKey:KMLFBHCUXQNWBZ-YPKPFQOOSA-N
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Compound Information
Molecular Weight:185.1788
Molecular Formula:C11H7NO2
InChIKey:PAZCLCHJOWLTGA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:124.1803
Molecular Formula:C8H12O
InChIKey:QYLFHLNFIHBCPR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:79.0999
Molecular Formula:C5H5N
InChIKey:Not Available
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Compound Information
Molecular Weight:162.7641
Molecular Formula:C4N4Ni
InChIKey:FUWOSUXMFKRUSS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:95.1424
Molecular Formula:C6H9N
InChIKey:YSGPDJCRZNUFBU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:181.3501
Molecular Formula:C10H19NSi
InChIKey:GDIUOOCMYUTMLI-MDZDMXLPSA-N
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Compound Information
Molecular Weight:26.0373
Molecular Formula:C2H2
InChIKey:HSFWRNGVRCDJHI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:161.2004
Molecular Formula:C10H11NO
InChIKey:MUZYAEDDOSKNRG-MRVPVSSYSA-N
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Compound Information
Molecular Weight:225.2609
Molecular Formula:C15H12FN
InChIKey:OAVUAKGAEPSSLW-LLVKDONJSA-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:109.1689
Molecular Formula:C7H11N
InChIKey:GCTNTYCHYKCHEK-SNAWJCMRSA-N
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Compound Information
Molecular Weight:164.158
Molecular Formula:C9H8O3
InChIKey:KNDQHSIWLOJIGP-DPTVFECHSA-N
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Compound Information
Molecular Weight:142.271
Molecular Formula:C7H14OSi
InChIKey:VZZROXZGVLAXPK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:203.2371
Molecular Formula:C12H13NO2
InChIKey:SJMWJWOXTULTRU-GHXNOFRVSA-N
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Compound Information
Molecular Weight:254.2408
Molecular Formula:C14H10N2O3
InChIKey:FWSUZMWCLXGFMB-ORCRQEGFSA-N
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Compound Information
Molecular Weight:80.088
Molecular Formula:C4H4N2
InChIKey:IAHFWCOBPZCAEA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:196.2445
Molecular Formula:C14H12O
InChIKey:UULPGUKSBAXNJN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:116.1598
Molecular Formula:C9H8
InChIKey:GHUURDQYRGVEHX-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:55.0785
Molecular Formula:C3H5N
InChIKey:Not Available
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Compound Information
Molecular Weight:169.2224
Molecular Formula:C12H11N
InChIKey:GFFBUAONLJRJBN-YKXYSFTHSA-N
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Compound Information
Molecular Weight:139.238
Molecular Formula:C9H17N
InChIKey:KOVZMYUXIJOHCD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:167.2481
Molecular Formula:C10H17NO
InChIKey:XPLVHGULHOCATM-VQHVLOKHSA-N
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Compound Information
Molecular Weight:95.1424
Molecular Formula:C6H9N
InChIKey:CSAZMTWHVNCILA-SNAWJCMRSA-N
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Compound Information
Molecular Weight:85.1045
Molecular Formula:C4H7NO
InChIKey:MWFMGBPGAXYFAR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:352.3634
Molecular Formula:C21H21O3P
InChIKey:FEVFLQDDNUQKRY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:211.2591
Molecular Formula:C14H13NO
InChIKey:QAILMFURFUYAJA-SNVBAGLBSA-N
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Compound Information
Molecular Weight:243.4194
Molecular Formula:C15H21NSi
InChIKey:VQVHCONRXUVXLI-KAMYIIQDSA-N
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Compound Information
Molecular Weight:159.2276
Molecular Formula:C11H13N
InChIKey:VSDRTHPRMPEAQI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:316.3102
Molecular Formula:C19H12N2O3
InChIKey:GPZZBPNDLRUJIP-UVTDQMKNSA-N
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Compound Information
Molecular Weight:1347.55
Molecular Formula:C72H60O12P4Pd
InChIKey:YPCSHBOPHWRBST-UHFFFAOYSA-N
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Compound Information
Molecular Weight:129.1586
Molecular Formula:C9H7N
InChIKey:ZWKNLRXFUTWSOY-QPJJXVBHSA-N
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Compound Information
Molecular Weight:138.594
Molecular Formula:C8H7Cl
InChIKey:KTZVZZJJVJQZHV-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:273.0393
Molecular Formula:C16H22Ni
InChIKey:SNNVSEONCOCCRZ-REBFVTMGSA-N
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Compound Information
Molecular Weight:110.1751
Molecular Formula:C7H11N
InChIKey:Not Available
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Compound Information
Molecular Weight:70.0898
Molecular Formula:C4H6O
InChIKey:NEEDEQSZOUAJMU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:187.2377
Molecular Formula:C12H13NO
InChIKey:YWNVQFSJHVSECD-GORDUTHDSA-N
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Compound Information
Molecular Weight:124.2233
Molecular Formula:C9H16
InChIKey:BBECVROIQDCRKP-UHFFFAOYSA-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:210.053
Molecular Formula:C12H10Fe
InChIKey:WHLDUFCKEYGQBS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:111.1418
Molecular Formula:C6H9NO
InChIKey:VHTDPFZJYKARNC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:37.833
Molecular Formula:BH4Na
InChIKey:YOQDYZUWIQVZSF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:108.1411
Molecular Formula:C6H8N2
InChIKey:GDCJAPJJFZWILF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:262.5225
Molecular Formula:CNNiY2
InChIKey:UOOKELFZYCARQA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:92.1384
Molecular Formula:C7H8
InChIKey:Not Available
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Compound Information
Molecular Weight:184.2338
Molecular Formula:C13H12O
InChIKey:DGQUMYDUFBBKPK-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:251.3984
Molecular Formula:C16H17NSi
InChIKey:DUFMBSZOXQMGLT-FOWTUZBSSA-N
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Compound Information
Molecular Weight:136.578
Molecular Formula:C8H5Cl
InChIKey:DGLHLIWXYSGYBI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:56.1063
Molecular Formula:C4H8
InChIKey:VXNZUUAINFGPBY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:215.3663
Molecular Formula:C13H17NSi
InChIKey:VUFVFFMVMLMUNN-ACCUITESSA-N
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Compound Information
Molecular Weight:231.3657
Molecular Formula:C13H17NOSi
InChIKey:CRSDLOLDICKRGV-ZRDIBKRKSA-N
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Compound Information
Molecular Weight:183.2475
Molecular Formula:C10H17NO2
InChIKey:YOYMGYLAJCBQAQ-POHAHGRESA-N
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Compound Information
Molecular Weight:223.4298
Molecular Formula:C13H25NSi
InChIKey:DLFCTITXDIQAHG-BENRWUELSA-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:81.1158
Molecular Formula:C5H7N
InChIKey:CFEYBLWMNFZOPB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:110.1968
Molecular Formula:C8H14
InChIKey:YKCQGTKPNABNLF-VOTSOKGWSA-N
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Compound Information
Molecular Weight:112.1265
Molecular Formula:C6H8O2
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:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:226.2307
Molecular Formula:C13H10N2O2
InChIKey:IFGOPYSXAQGKJY-MBXJOHMKSA-N
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Compound Information
Molecular Weight:240.2142
Molecular Formula:C13H8N2O3
InChIKey:JTJKEWXYLQDBAZ-ONEGZZNKSA-N
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Compound Information
Molecular Weight:139.2703
Molecular Formula:C7H13NSi
InChIKey:NHQPNZAFPRDQNL-ALCCZGGFSA-N
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Compound Information
Molecular Weight:115.601
Molecular Formula:C3H2CuN
InChIKey:ACOJRKNNSZWVRW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:137.2221
Molecular Formula:C9H15N
InChIKey:YHUYWJCMEUVGIJ-AATRIKPKSA-N
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Compound Information
Molecular Weight:223.4298
Molecular Formula:C13H25NSi
InChIKey:WDQAYZUTDRMMRD-VAWYXSNFSA-N
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Compound Information
Molecular Weight:174.3144
Molecular Formula:C11H14Si
InChIKey:UZIXCCMXZQWTPB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:134.1751
Molecular Formula:C9H10O
InChIKey:UAJRSHJHFRVGMG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:129.599
Molecular Formula:Cl2Ni
InChIKey:QMMRZOWCJAIUJA-UHFFFAOYSA-L
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Compound Information
Molecular Weight:125.2114
Molecular Formula:C8H15N
InChIKey:DPGVNSDPGIWYQK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:145.201
Molecular Formula:C10H11N
InChIKey:IZPUPXNVRNBDSW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:183.249
Molecular Formula:C13H13N
InChIKey:ZPGITZNAWPZYAG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:165.2753
Molecular Formula:C11H19N
InChIKey:CSOYLNBIVCLGSZ-ZJUUUORDSA-N
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Compound Information
Molecular Weight:132.1592
Molecular Formula:C9H8O
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:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:150.2209
Molecular Formula:C9H14N2
InChIKey:IERAUDYEBKFNFZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:199.2054
Molecular Formula:C12H9NO2
InChIKey:COPWPECHFWIYSP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:172.1471
Molecular Formula:C9H7F3
InChIKey:CEWDRCQPGANDRS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:211.2591
Molecular Formula:C14H13NO
InChIKey:RRFXDURUCCMHIA-UHFFFAOYSA-N
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