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catecholborane
Sign in to saveCatecholborane (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.
Chemical data
- Formula
- C6H5BO2
- Molecular weight
- 119.92 g/mol
- IUPAC name
- 1,3,2-benzodioxaborole
- SMILES
- B1OC2=CC=CC=C2O1
- InChIKey
- CENMEJUYOOMFFZ-UHFFFAOYSA-N
- Polar surface area
- 18.5 Ų
- H-bond donors
- 0
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Wikidata facts
- Subclass of
- chemical compound
- Has part
- hydrogen
- Mass
- 120.038
Show 4 more facts
- chemical formula
- C₆H₅BO₂
- canonical SMILES
- B1OC2=CC=CC=C2O1
- melting point
- 12.0
- Commons category
- Catecholborane
Sources (2)
via Wikidata · CC0
~2 min read
Encyclopedic overview
3 sectionsContents
- 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.
Excerpted from Wikipedia’s “catecholborane” article, available under the CC BY-SA 4.0 licence.