Standard Article

Formation of Carbon[BOND]Carbon and Carbon[BOND]Heteroatom Bonds via Organoboranes and Organoborates

  1. Ei-Ichi Negishi1,
  2. Michael J. Idacavage2

Published Online: 15 OCT 2004

DOI: 10.1002/0471264180.or033.01

Organic Reactions

Organic Reactions

How to Cite

Negishi, E.-I. and Idacavage, M. J. 2004. Formation of Carbon[BOND]Carbon and Carbon[BOND]Heteroatom Bonds via Organoboranes and Organoborates. Organic Reactions. 33:1:1–246.

Author Information

  1. 1

    Purdue University, West Lafayette, Indiana

  2. 2

    Tennessee Eastman Company, Kingsport, Tennessee

Publication History

  1. Published Online: 15 OCT 2004

Chemistry Terms

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Abstract

Until recently the use of organometallics as discrete reagents and intermediates in organic synthesis had been largely restricted to a relatively few classes or compounds, such as those containing lithium and magnesium. Mainly within the last two decades, organocopper compounds and organoboron compounds have emerged as versatile and useful reagents and intermediates in organic synthesis. Except for carboranes, organoboron compounds generally exist either as tricoordinate or as tetracoordinate species. The trisubstituted derivatives of boron are called boranes, which may exist either as essentially trigonal planar monomeric species or as aggregates in which the boron atoms occupy the central position of an essentially tetrahedral configuration. In fact, essentially all monoorganoboranes (RBH2) and diorganoboranes (R2BH) as well as the parent borane (BH3) exist as the dimers, whereas triorganoboranes (R3B) are usually monomeric. For the sake of simplicity, however, all of these compounds are treated as monomers in this chapter, except when such a simplification is unacceptable. This chapter describes some of the key features common to various organoboron reactions used for the formation of carbon[BOND]carbon and carbon[BOND]heteroatom bonds and summarizes the available information on these reactions according to the product types. Hydration of olefins and acetylenes via hydroboration–oxidation was reviewed earlier, and this chapter does not update this reaction. Also excluded is a detailed discussion of the synthesis of olefins and acetylenes via organoboron compounds.

Keywords:

  • carbon-carbon bonds;
  • carbon-heteroatom bonds;
  • organoboranes;
  • organoborates;
  • organoboron properties;
  • ionic reactions;
  • free-radical reactions;
  • concerted reactions;
  • nucleophilic reagents;
  • compound preparations;
  • alcohols;
  • ethers;
  • peroxides;
  • ketones;
  • aldehydes;
  • carboxylic acids;
  • nitriles;
  • amines;
  • halides;
  • sulfur derivatives;
  • alkanes;
  • cycloalkanes;
  • arenes;
  • handling;
  • homologation;
  • direct functionalization;
  • experimental procedures

Featured Compounds

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  1. 1 - 250
Compound Information
Molecular Weight:0
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:245.897
Molecular Formula:C4H6Br2O2
InChIKey:NIJGVVHCUXNSLL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:278.238
Molecular Formula:C17H31BO2
InChIKey:GRLMVGSRNNQLIN-KPWZGGAESA-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:70.95
Molecular Formula:C4H12B
InChIKey:OTRGZYHRJNPTDC-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:85.941
Molecular Formula:C4H11BO
InChIKey:DUGVUDOTENHWBU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:41.888
Molecular Formula:C2H7B
InChIKey:GMLFPSKPTROTFV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:324.351
Molecular Formula:C23H37B
InChIKey:NZLZBKBORWFTCN-NZQKXSOJSA-N
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Compound Information
Molecular Weight:204.138
Molecular Formula:C9H21BO2S
InChIKey:XQHPMUKVGRQQKS-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:88.1051
Molecular Formula:C4H8O2
InChIKey:KQNPFQTWMSNSAP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:233.178
Molecular Formula:C15H27BO
InChIKey:FLTRTTGVPIVTHN-OKILXGFUSA-N
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Compound Information
Molecular Weight:74.1216
Molecular Formula:C4H10O
InChIKey:LRHPLDYGYMQRHN-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:310.5899
Molecular Formula:C19H38OSi
InChIKey:NVCIIOXTJRQLEC-DAPNLKQXSA-N
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Compound Information
Molecular Weight:120.1485
Molecular Formula:C8H8O
InChIKey:KWOLFJPFCHCOCG-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:57.887
Molecular Formula:C2H7BO
InChIKey:HWEKVSRZLQDNFL-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:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:136.042
Molecular Formula:C9H17B
InChIKey:ANIBJGMYKRVYRR-DTORHVGOSA-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:97.994
Molecular Formula:C6H15B
InChIKey:DFZFZKDSPYJVRQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:383.469
Molecular Formula:C21H44BO3Si
InChIKey:HHGOMIPZCCMKCN-PBVLPULHSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:182.2594
Molecular Formula:C11H18O2
InChIKey:UKVHBICLWAMLSG-PSFRMBJNSA-N
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Compound Information
Molecular Weight:200.3193
Molecular Formula:C15H20
InChIKey:ODLBQNUFNHSRSH-GXTWGEPZSA-N
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Compound Information
Molecular Weight:80.1277
Molecular Formula:C6H8
InChIKey:UCAJIFZNHMIWOD-ARJAWSKDSA-N
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Compound Information
Molecular Weight:319.227
Molecular Formula:C24H20B
InChIKey:SVHQOIWIRUVWII-UHFFFAOYSA-N
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Compound Information
Molecular Weight:157.008
Molecular Formula:C6H5Br
InChIKey:QARVLSVVCXYDNA-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:279.961
Molecular Formula:C11H16BO2Y
InChIKey:OLNOEQQTUVJRFM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:268.986
Molecular Formula:C12H18BBrO
InChIKey:RBWXKSSYEIKZHH-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:429.915
Molecular Formula:C12H21BI2
InChIKey:HWKHIZQWLRGYOE-DEFDFUCDSA-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:114.1424
Molecular Formula:C6H10O2
InChIKey:Not Available
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Compound Information
Molecular Weight:147.187
Molecular Formula:C9H18LiN
InChIKey:ANYSGBYRTLOUPO-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:172.874
Molecular Formula:C5H13BY
InChIKey:NWEWDPVBIXWHSV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:192.89
Molecular Formula:C6H14BBrO
InChIKey:IWBGHKOCDNFBSN-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:82.1436
Molecular Formula:C6H10
InChIKey:ATQUFXWBVZUTKO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:180.138
Molecular Formula:C12H25B
InChIKey:ZUFVXWXRFALUEY-GHMZBOCLSA-N
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Compound Information
Molecular Weight:83.925
Molecular Formula:C4H9BO
InChIKey:VPNZFCXDZNALQU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:126.004
Molecular Formula:C7H15BO
InChIKey:NGRRUCZXHPPOBR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:244.35
Molecular Formula:C12H20O3S
InChIKey:JVCVCCWIWQKHLH-RYUDHWBXSA-N
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Compound Information
Molecular Weight:83.925
Molecular Formula:C4H9BO
InChIKey:CJUNGBWZFFDLJX-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:102.1748
Molecular Formula:C6H14O
InChIKey:FRDAATYAJDYRNW-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:205.092
Molecular Formula:C4H6BrKO2
InChIKey:FSAQQQJPLVAJKY-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:69.1051
Molecular Formula:C4H7N
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:168.2344
Molecular Formula:C13H12
InChIKey:RJFCFNWLPJRCLR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:200.3178
Molecular Formula:C12H24O2
InChIKey:ANRXOJOPPWWPFQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:184.084
Molecular Formula:C10H21BO2
InChIKey:SSNGEJWRGYZURW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:309.317
Molecular Formula:C22H34B
InChIKey:QXSCAFOORDZBQZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:141.975
Molecular Formula:C9H16BLi
InChIKey:KUSOJEODGIEUOS-UFIFRZAQSA-N
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Compound Information
Molecular Weight:142.1971
Molecular Formula:C11H10
InChIKey:QPUYECUOLPXSFR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:140.567
Molecular Formula:C7H5ClO
InChIKey:PASDCCFISLVPSO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:71.914
Molecular Formula:C3H9BO
InChIKey:BEQHHTPEGVHORR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:129.786
Molecular Formula:C2H6BY
InChIKey:XBIJSCHGDLCIMC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:253.80894
Molecular Formula:I2
InChIKey:PNDPGZBMCMUPRI-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:198.3034
Molecular Formula:C15H18
InChIKey:RJFYXVFTHRILQA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:114.1026
Molecular Formula:C4H6N2O2
InChIKey:Not Available
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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:102.1317
Molecular Formula:C5H10O2
InChIKey:Not Available
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Compound Information
Molecular Weight:79.904
Molecular Formula:Br
InChIKey:CPELXLSAUQHCOX-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:140.074
Molecular Formula:C9H21B
InChIKey:IGYMXJAKCCTKLR-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:27.67
Molecular Formula:B2H6
InChIKey:NTJHUEGHVSASEP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:299.098
Molecular Formula:C15H28BBr
InChIKey:CHPSXEJBYNPGKS-JNCUSGHUSA-N
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Compound Information
Molecular Weight:54.0904
Molecular Formula:C4H6
InChIKey:XNMQEEKYCVKGBD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:80.034
Molecular Formula:C3H10AlLi
InChIKey:IDMCLWTVKFBGJC-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:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:83.968
Molecular Formula:C5H13B
InChIKey:OLQDJDHZXQUDLN-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:118.96
Molecular Formula:C3H3Br
InChIKey:YORCIIVHUBAYBQ-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:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:342.1
Molecular Formula:C16H27BBrO2
InChIKey:QYVCJRICPQZINP-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:181.313
Molecular Formula:C6H5BrMg
InChIKey:ANRQGKOBLBYXFM-UHFFFAOYSA-M
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Compound Information
Molecular Weight:16.0425
Molecular Formula:CH4
InChIKey:VNWKTOKETHGBQD-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:74.509
Molecular Formula:C3H3Cl
InChIKey:OMNGRPHPKWAMSY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:179.012
Molecular Formula:C5H7BrO2
InChIKey:UJTJVQIYRQALIK-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:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:245.232
Molecular Formula:C17H30B
InChIKey:JRQUBVQNAIIUCP-JWTNVVGKSA-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: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:224.3392
Molecular Formula:C14H24O2
InChIKey:LLRZUAWETKPZJO-SCFJQAPRSA-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:34.0147
Molecular Formula:H2O2
InChIKey:MHAJPDPJQMAIIY-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:172.2215
Molecular Formula:C9H16O3
InChIKey:DRCZMZMAKZTSNZ-GCJDJSOWSA-N
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Compound Information
Molecular Weight:124.2233
Molecular Formula:C9H16
InChIKey:SWLGTNLRTUGMHV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:98.0999
Molecular Formula:C5H6O2
InChIKey:FMVJYQGSRWVMQV-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:221.908
Molecular Formula:C7H15BBrO2
InChIKey:DTJSVIHUTPXDJR-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:210.854
Molecular Formula:C5H9BCl2N2O2
InChIKey:FJWOXATXFNSLRR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:88.9064
Molecular Formula:Y
InChIKey:MBFPTUZZFCMKBA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:165.9604
Molecular Formula:C3H3I
InChIKey:JHUPGXNKUPOSIE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:150.1745
Molecular Formula:C9H10O2
InChIKey:QUKGYYKBILRGFE-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:114.096
Molecular Formula:CH3FO3S
InChIKey:MBXNQZHITVCSLJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:421.91
Molecular Formula:C9H9O2WY
InChIKey:JXPCDVPBBZMAGP-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:162.864
Molecular Formula:C5H12BBr
InChIKey:MDMZVOKJMOLHTM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:102.9324
Molecular Formula:CH2Y
InChIKey:RGHPXSUCKMQQLI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:210.847
Molecular Formula:C2H2BrOY
InChIKey:DAEHETISIZUPBH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:309.272
Molecular Formula:C18H35BO3
InChIKey:NNFGJWSHTHAVBC-YICAPOETSA-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:113.029
Molecular Formula:C7H18B
InChIKey:KIMXOBSNVNTMBX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:309.272
Molecular Formula:C18H34BO3
InChIKey:CLVAICBWCQFOAP-AJRJYLBASA-N
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Compound Information
Molecular Weight:264.995
Molecular Formula:C10H22BBrO2
InChIKey:QHLBLYJRVGGVJS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:266.313
Molecular Formula:C18H39B
InChIKey:NMHWWOSZMMORNT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:42.0797
Molecular Formula:C3H6
InChIKey:LVZWSLJZHVFIQJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:82.96
Molecular Formula:C5H12B
InChIKey:MQZFOUNLTZKYKZ-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:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:171.034
Molecular Formula:C7H7Br
InChIKey:AGEZXYOZHKGVCM-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:112.212
Molecular Formula:C4H9KO
InChIKey:LPNYRYFBWFDTMA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:222.3233
Molecular Formula:C14H22O2
InChIKey:DURIUTOEEZMTFC-VOTSOKGWSA-N
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Compound Information
Molecular Weight:264.926
Molecular Formula:C10H13BO2Y
InChIKey:BSFIWSMUZINIGB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:83.925
Molecular Formula:C4H9BO
InChIKey:WMOIHBBBDSDLGG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:113.994
Molecular Formula:C6H15BO
InChIKey:BUUAJZSUUNKOCX-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:258.185
Molecular Formula:C12H23BO3S
InChIKey:LGGJDMIQXVBHOY-USZNOCQGSA-N
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Compound Information
Molecular Weight:154.2078
Molecular Formula:C12H10
InChIKey:ZUOUZKKEUPVFJK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:95.978
Molecular Formula:C6H13B
InChIKey:XXZSKSHQTBJODO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:251.161
Molecular Formula:C10H19BrO2
InChIKey:JIQJOKSCSVMZAN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:124.032
Molecular Formula:C8H17B
InChIKey:JZIHKNPGGYMQOB-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:176.89
Molecular Formula:C6H14BBr
InChIKey:DMWXXCZVBUYMOM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:141.939
Molecular Formula:CH3I
InChIKey:INQOMBQAUSQDDS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:124.2233
Molecular Formula:C9H16
InChIKey:NFYFJWQJPKMCNP-KRALRXKRSA-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:100.1158
Molecular Formula:C5H8O2
InChIKey:JIGUQPWFLRLWPJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:142.004
Molecular Formula:C7H15BO2
InChIKey:WHFJBSCBGJTQQG-FNORWQNLSA-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:97.994
Molecular Formula:C6H15B
InChIKey:LALRXNPLTWZJIJ-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:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:375.417
Molecular Formula:C24H44BO2
InChIKey:MKSHWSKTJWVYRZ-OBGWFSINSA-N
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Compound Information
Molecular Weight:116.1583
Molecular Formula:C6H12O2
InChIKey:OBNCKNCVKJNDBV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:206.175
Molecular Formula:C14H27B
InChIKey:RSWRKJUOKNUVNQ-SEYXRHQNSA-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:118.96
Molecular Formula:C3H3Br
InChIKey:XXFUZSHTIOFGNV-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:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:53.0626
Molecular Formula:C3H3N
InChIKey:NLHHRLWOUZZQLW-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:58.0791
Molecular Formula:C3H6O
InChIKey:CSCPPACGZOOCGX-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:120.976
Molecular Formula:C3H5Br
InChIKey:BHELZAPQIKSEDF-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:83.925
Molecular Formula:C4H9BO
InChIKey:GQALGDNPGIPNJI-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:28.0101
Molecular Formula:CO
InChIKey:UGFAIRIUMAVXCW-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:262.195
Molecular Formula:C16H27BO2
InChIKey:FHQJRADVNPUKRH-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:159.808
Molecular Formula:Br2
InChIKey:GDTBXPJZTBHREO-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:166.9485
Molecular Formula:C2H2IN
InChIKey:VODKOOOHHCAWFR-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:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:83.925
Molecular Formula:C4H9BO
InChIKey:FHQRDEAEZNLTSN-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:324.351
Molecular Formula:C23H37B
InChIKey:MKYKTBHQAMSESR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:96.752
Molecular Formula:CH3BCl2
InChIKey:WRWXDQSBUPVVPD-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:112.2126
Molecular Formula:C8H16
InChIKey:SZFRZEBLZFTODC-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:154.101
Molecular Formula:C10H23B
InChIKey:HXJFQNUWPUICNY-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:CZDVGHJZLVSCHY-MYPVRGOXSA-N
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Compound Information
Molecular Weight:152.085
Molecular Formula:C10H21B
InChIKey:ZZNPDDKYQVSSEO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:218.2915
Molecular Formula:C14H18O2
InChIKey:IUHDSXBIHIDQJV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:148.223
Molecular Formula:C6H12O2S
InChIKey:HOKIBTXDUCLZQR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:224.0464
Molecular Formula:C8H7O2Y
InChIKey:RABMYTAFZAXGAY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:83.925
Molecular Formula:C4H9BO
InChIKey:PZGBVLFGJZZOHQ-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:55.915
Molecular Formula:C3H9B
InChIKey:WXRGABKACDFXMG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:84.1595
Molecular Formula:C6H12
InChIKey:Not Available
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Compound Information
Molecular Weight:129.993
Molecular Formula:C6H15BO2
InChIKey:MCWRANLOZJVSSB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:142.004
Molecular Formula:C7H15BO2
InChIKey:IXSCIGGOPNHDPQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:15.0345
Molecular Formula:CH3
InChIKey:VNWKTOKETHGBQD-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:16.0425
Molecular Formula:CH4
InChIKey:VNWKTOKETHGBQD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:224.0464
Molecular Formula:C8H7O2Y
InChIKey:RABMYTAFZAXGAY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:82.96
Molecular Formula:C5H12B
InChIKey:OLQDJDHZXQUDLN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:80.912
Molecular Formula:BrH
InChIKey:CPELXLSAUQHCOX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:16.0425
Molecular Formula:CH4
InChIKey:VNWKTOKETHGBQD-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:324.351
Molecular Formula:C23H37B
InChIKey:NZLZBKBORWFTCN-REWPJTCUSA-N
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Compound Information
Molecular Weight:31.9988
Molecular Formula:O2
InChIKey:MHAJPDPJQMAIIY-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:83.968
Molecular Formula:C5H13B
InChIKey:OLQDJDHZXQUDLN-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:130.1418
Molecular Formula:C6H10O3
InChIKey:UAGJVSRUFNSIHR-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:165.576
Molecular Formula:C8H4ClNO
InChIKey:USEDMAWWQDFMFY-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: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: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:58.0791
Molecular Formula:C3H6O
InChIKey:NBBJYMSMWIIQGU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:86.1323
Molecular Formula:C5H10O
InChIKey:BTSIZIIPFNVMHF-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:172.2231
Molecular Formula:C12H12O
InChIKey:NBHPCXYPNADLSA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:134.1751
Molecular Formula:C9H10O
InChIKey:KRIOVPPHQSLHCZ-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:468.308
Molecular Formula:C27H42B2O3S
InChIKey:VRRJYDMSZYWWPI-OQQNJPJOSA-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:201.076
Molecular Formula:C11H16BN3
InChIKey:IUFLOLGISXHXNA-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:130.1418
Molecular Formula:C6H10O3
InChIKey:VVCYNVCCODBCOE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:100.1589
Molecular Formula:C6H12O
InChIKey:BVIJQMCYYASIFP-WDSKDSINSA-N
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Compound Information
Molecular Weight:76.333
Molecular Formula:C2H6BCl
InChIKey:DJGJBRMHVVAZOU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:212.138
Molecular Formula:C15H21B
InChIKey:IQRBNRFCRAJXJF-GASCZTMLSA-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:191.52
Molecular Formula:C6H5ClSe
InChIKey:WJCXADMLESSGRI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:194.3132
Molecular Formula:C13H22O
InChIKey:CGXWFXFSNKASOW-NGBBIHDVSA-N
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