Diphenylphosphine

Structural formula
General
Surname	Diphenylphosphine
other names	Diphenylphosphine
Molecular formula	C 12 H 11 P
Brief description	colorless liquid
External identifiers / databases
EC number	212-591-4
ECHA InfoCard	100.011.447
PubChem	70017
Wikidata	Q413810
properties
Molar mass	186.19 g · mol -1
Physical state	liquid
density	1.07 g cm −3 (20 ° C)
Melting point	−14.5 ° C
boiling point	280 ° C
Vapor pressure	2.7 h Pa (110 ° C)
Refractive index	1.626
safety instructions
H and P phrases	H: 250-315-319-335
	P: 222-231-261-305 + 351 + 338-422
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Diphenylphosphine is a chemical compound from the group of phosphines .

Manufacturing

Diphenylphosphine can be obtained by the hydrogenation of chlorodiphenylphosphine with lithium aluminum hydride .

The reaction of triphenylphosphine with elemental lithium also gives diphenylphosphine.

{\ displaystyle \ mathrm {PPh_ {3} \ + \ 2Li \ longrightarrow \ LiPPh_ {2} \ + \ LiPh}}

Reaction of triphenylphosphine with lithium to dipenylphosphine. The products are released from the lithiated compounds by aqueous work-up. Ph = phenyl

properties

Diphenylphosphine is a colorless liquid that melts at −14.5 ° C and boils at 280 ° C. Diphenylphosphine is a very weak acid and only reacts with strong bases to form the diphenylphosphide anion , which is stabilized by mesomerism .

use

The anion of diphenylphosphine (Ph ₂ P ^- ) can be obtained by reaction with basic salts of, for example, potassium or lithium . The anion can be used as a nucleophile in substitution reactions . This is for example for the synthesis of phosphine ligand such as dppm or dppp used. Similar to thiolates, it can serve to deprotect aromatic methoxy groups, in which case significantly milder conditions are required. Even boiling THF is sufficient, although 150 ° C are often required for thiolates.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f Datasheet Diphenylphosphine from Sigma-Aldrich , accessed on March 28, 2011 ( PDF ).
^ E. Wiberg, M. van Ghemen, G. Müller-Schiedmayer: News from the chemistry of polyphosphanes , in: Angew. Chem. , 1963 , 75 , pp. 814-823.
^ HR Hudson, AR Qureshi, D. Ragoonanan: Factors in the formation of isomerically and optically pure alkyl halides. Part IX. Reactions of (1-substituted n-alkyl) diphenylphosphinites with hydrogen halides and with halogens , in: J. Chem. Soc., Perkin Trans. 1 , 1972 , pp. 1595-1597.
↑ D. Wittenberg, H. Gilman: Lithium Cleavages of Triphenyl Derivatives of Some Group Vb Elements in Tetrahydrofuran , in: J. Org. Chem. , 1958 , 23, pp. 1063-1065.
↑ EN Tsvetkov, NA Bondarenko, IG Malakhova, MI Kabachnik, in: Synthesis , 1986 , 3 , pp. 198-208.
↑ MT Honaker, BJ Sandefur, JL Hargett, AL McDaniel, RN Salvatore, in: Tetrahedron Lett. , 2003 , 44, 46, pp. 8373-8378.

[Sigma-1] ↑ ^a ^b ^c ^d ^e ^f Datasheet Diphenylphosphine from Sigma-Aldrich , accessed on March 28, 2011 ( PDF ).

[2] E. Wiberg, M. van Ghemen, G. Müller-Schiedmayer: News from the chemistry of polyphosphanes , in: Angew. Chem. , 1963 , 75 , pp. 814-823.

[3] HR Hudson, AR Qureshi, D. Ragoonanan: Factors in the formation of isomerically and optically pure alkyl halides. Part IX. Reactions of (1-substituted n-alkyl) diphenylphosphinites with hydrogen halides and with halogens , in: J. Chem. Soc., Perkin Trans. 1 , 1972 , pp. 1595-1597.

[4] D. Wittenberg, H. Gilman: Lithium Cleavages of Triphenyl Derivatives of Some Group Vb Elements in Tetrahydrofuran , in: J. Org. Chem. , 1958 , 23, pp. 1063-1065.

[5] EN Tsvetkov, NA Bondarenko, IG Malakhova, MI Kabachnik, in: Synthesis , 1986 , 3 , pp. 198-208.

[6] MT Honaker, BJ Sandefur, JL Hargett, AL McDaniel, RN Salvatore, in: Tetrahedron Lett. , 2003 , 44, 46, pp. 8373-8378.