Triphenylborane

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Triphenylborane
Names
Preferred IUPAC name
Triphenylborane
Identifiers
3D model (
JSmol
)
ChemSpider
ECHA InfoCard
 100.012.277 Edit this at Wikidata
EC Number
  • 213-504-2
UNII
  • InChI=1S/C18H15B/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H checkY
    Key: MXSVLWZRHLXFKH-UHFFFAOYSA-N checkY
  • InChI=1/C18H15B/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H
    Key: MXSVLWZRHLXFKH-UHFFFAOYAV
  • B(c1ccccc1)(c2ccccc2)c3ccccc3
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
GHS labelling:
GHS02: Flammable
Warning
H228
P210, P240, P241, P280, P370+P378
Related compounds
Related
isoelectronic
Triphenylmethyl
cation
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Triphenylborane, often abbreviated to BPh3 where Ph is the

aromatic solvents
.

Structure and properties

The core of the compound, BC3, has a

phenyl groups are rotated at about a 30° angle from the core plane.[1]

Even though triphenylborane and

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.[2]

Synthesis

Triphenylborane was first synthesized in 1922.

boron trifluoride diethyl etherate and the Grignard reagent, phenylmagnesium bromide.[4]

BF3•O(C2H5)2 + 3 C6H5MgBr → B(C6H5)3 + 3 MgBrF + (C2H5)2O

Triphenylborane can also be synthesized on a smaller scale by the thermal decomposition of trimethylammonium tetraphenylborate.[5]

[B(C6H5)4][NH(CH3)3] → B(C6H5)3 + N(CH3)3 + C6H6

Applications

Triphenylborane is made commercially by a process developed by

haloaromatic (chlorobenzene), and a secondary alkyl borate ester.[6]

Triphenylborane can be used to make

acrylic esters.[6]

References

  1. doi:10.1016/S0022-328X(00)81488-6
    .
  2. PMID 15909033
    .
  3. doi:10.1002/cber.19220550513
    .
  4. ISBN 978-0-470-13246-3. {{cite book}}: |journal= ignored (help
    )
  5. doi:10.1002/jlac.19515730118
    .
  6. ^
    doi:10.1002/14356007.a04_309
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