Triphenylphosphine

  • Triphenylphosphine
  • Triphenylphosphorus
  • Triphenylphosphid
  • Phosphortriphenyl
  • PPh3

Colorless, monoclinic prisms tribolumineszierende

Fixed

1.19 g · cm -3 ( 20 ° C)

80 ° C.

360 ° C.

1 Pa (88 ° C)

  • Insoluble in water (0.1 mg · l-1 at 25 ° C)
  • Soluble in ethanol, and many organic solvents

1.6358 (80 ° C)

Attention

5 mg · m-3

700 mg · kg -1 ( LD50, rat, oral)

Template: Infobox chemical / molecular formula search available

Triphenylphosphine (also: triphenylphosphine, triphenylphosphorus, Phosphortriphenyl, English: triphenylphosphine, triphenylphosphanes ) is a ligand ( complexing agent ) for the preparation of metal complexes, which are required in chemical synthesis.

Properties

Triphenylphoshan forms colorless, characteristic odor crystals with a melting point of about 80 ° C and boiling point of 360 ° C, which are not water soluble, but rather well soluble in organic solvents. Triphenylphosphine readily forms transition metal complexes in organic solvents ( solvents) to solve and are often valuable for the synthesis. Over time formed triphenylphosphine oxide in the air.

Production

On a laboratory scale can be represented by the action of triphenylphosphine of phenylmagnesium bromide or phenyl lithium to phosphorus trichloride. Industry, the production of phosphorus trichloride, chlorine, and sodium benzene.

Use

Triphenylphosphine is part of the Wittig reagent, which on the industrial scale for the synthesis of vitamin A ( = retinol) and olefins is required. Another important large-scale structure of reaction is the modern version of the hydroformylation ( also: oxo synthesis ), in which a rhodium complex of triphenylphosphane is used here react alkenes with carbon monoxide and hydrogen to valuable aldehydes. These are usually further processed to important alcohols. Triphenylphosphine is used on a laboratory scale for the preparation of esters, ethers, amides and thioethers in the Mitsunobu reaction. Furthermore, triphenylphosphine is used in the laboratory as part of the Staudinger reaction, are synthesized in the primary amines from azides. Continue to play triphenylphosphine as a ligand of the palladium catalyst, a role, such as the Heck reaction or Sonogashira coupling (such as (PPh3) 2PdCl2, or (PPh3) Pd). Sometimes also the arsenic analogue triphenylarsine is used there.

Structure

Filling model of the triphenylphosphine.

CAS registry number Vapor pressure Dangerous Substances Directive (67/548/EEC) Chlorobenzene Wittig reaction CRC Handbook of Chemistry and Physics Digital Object Identifier
659080
de