Triphenylborane
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IUPAC name
Triphenylborane
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3D model (Jmol)
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| ChemSpider | |
| ECHA InfoCard | 100.012.277 |
| EC Number | 213-504-2 |
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PubChem CID
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| Properties | |
| C18H15B | |
| Molar mass | 242.12 g/mol |
| Appearance | White crystals |
| Melting point | 142 °C (288 °F; 415 K) |
| Boiling point | 203 °C (397 °F; 476 K) (15 mmHg) |
| Insoluble | |
| Structure | |
| trigonal planar | |
| Hazards | |
| R-phrases (outdated) | R11 |
| S-phrases (outdated) | S16 S22 S24/25 |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Infobox references | |
Triphenylborane, often abbreviated to BPh3 where Ph is the phenyl group C6H5-, is a chemical compound with the formula B(C6H5)3. It is a white crystalline solid and is both air and moisture sensitive, slowly forming benzene and triphenylboroxine. It is soluble in aromatic solvents.
The core of the compound, BC3, has a trigonal planar structure. The phenyl groups are rotated at about a 30° angle from the core plane.
Even though triphenylborane and tris(pentafluorophenyl)borane are structurally similar, their Lewis acidity is not. BPh3 is a weak Lewis acid while B(C6F5)3 is a strong Lewis acid due to the electronegativity of the fluorine atoms. Other boron Lewis acids include BF3 and BCl3.
Triphenylborane was first synthesized in 1922. It is typically made with boron trifluoride diethyl etherate and the Grignard reagent, phenylmagnesium bromide.
Triphenylborane can also be synthesized on a smaller scale by the thermal decomposition of trimethylammonium tetraphenylborate.
Triphenylborane is made commercially by a process developed by Du Pont for use in its hydrocyanation of butadiene to adiponitrile, a nylon intermediate. Du Pont produces triphenylborane by reacting sodium metal, a haloaromatic (chlorobenzene), and a secondary alkyl borate ester.
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