Triphenylborane

From Wikipedia, the free encyclopedia
Triphenylborane
Structural formula of triphenylborane.svg
Triphenylborane-from-xtal-1974-3D-balls.png
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
Signal word
 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).
☒N  (what is checkY☒N ?)
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 . It is soluble in aromatic solvents.

Structure and properties[]

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.[1]

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.[2]

Synthesis[]

Triphenylborane was first synthesized in 1922.[3] It is typically made with 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 .[5]

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

Applications[]

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 .[6]

Triphenylborane can be used to make , such as . Triarylborane amine complexes are used as catalysts for the polymerization of .[6]

References[]

  1. ^ Zettler, F.; Hausen, H. D.; Hess, H. (1974). "Crystal and Molecular Structure of Triphenylborane". J. Organomet. Chem. 72 (2): 157. doi:10.1016/S0022-328X(00)81488-6.
  2. ^ Erker, G. (2005). "Tris(pentafluorophenyl)borane: a special boron Lewis acid for special reactions". Dalton Trans. (11): 1883–90. doi:10.1039/b503688g. PMID 15909033.
  3. ^ E. Krause & R. Nitsche (1922). "Darstellung von organischen Bor-Verbindungen mit Hilfe von Borfluorid, II.: Bortriphenyl und Phenyl-borsäure". Chemische Berichte. 55 (5): 1261. doi:10.1002/cber.19220550513.
  4. ^ R. Köster; P. Binger & W. Fenzl (1974). Triphenylborane. Inorg. Synth. Inorganic Syntheses. 15. pp. 134–136. doi:10.1002/9780470132463.ch30. ISBN 978-0-470-13246-3.
  5. ^ G. Wittig; P. Raff (1951). "Über Komplexbildung mit Triphenyl-bor". Liebigs Annalen der Chemie. 573: 195. doi:10.1002/jlac.19515730118.
  6. ^ a b C. R. Guibert and J. L. Little, “Alkyl- and Arylboranes,” Ullmanns’s Encyclopedia of Industrial Chemistry, Wiley-VCH Verlag, Weinheim, 2005. doi:10.1002/14356007.a04_309
Retrieved from ""