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catecholborane

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Catecholborane (abbreviated HBcat) is an organoboron compound that is useful in organic synthesis. This colourless liquid is a derivative of catechol and a borane, having the formula C6H4O2BH.

Wikidata facts

Mass
120.038
Show 4 more facts
chemical formula
C₆H₅BO₂
canonical SMILES
B1OC2=CC=CC=C2O1
melting point
12.0
Commons category
Catecholborane
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Contents
  • Synthesis and structure
  • Reactions
  • References

Catecholborane (abbreviated HBcat) is an organoboron compound that is useful in organic synthesis. This colourless liquid is a derivative of catechol and a borane, having the formula C6H4O2BH.

==Synthesis and structure== Traditionally catecholborane is produced by treating catechol with borane (BH3) in a cooled solution of THF. However, this method results in a loss of 2 mole equivalents of the hydride. Nöth and Männig described the reaction of alkali-metal boron hydride (LiBH4, NaBH4, KBH4) with tris(catecholato)bisborane in an ethereal solvent such as diethyl ether. In 2001, Herbert Brown and coworkers prepared catecholborane by treatment of tri-o-phenylene bis-borate with diborane.

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