Triphenylarsine

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Triphenylarsine
Ball and stick model of aromatic triphenylarsine
Identifiers
CAS number 603-32-7 YesY
PubChem 11773
ChemSpider 11280 YesY
EC number 210-032-9
UN number 3465
RTECS number CH8942500
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C18H15As
Molar mass 306.23 g mol−1
Appearance Colourless solid
Density 1.395 g cm−3
Melting point 58 to 61 °C (136 to 142 °F; 331 to 334 K)
Boiling point 373 °C (703 °F; 646 K) at 760 mmHg
Solubility in water Insoluble
Solubility Soluble in ethyl ether, benzene, slightly soluble in ethanol
Structure
Crystal structure Triclinic
Hazards
EU classification Toxic TDangerous for the Environment (Nature) N
R-phrases R23/25, R50/53
S-phrases S20/21, S28, S45, S60, S61
Related compounds
Related organoarsanes Trimethylarsine
Related compounds Triphenylamine

Triphenylborane
Triphenylphosphine
Triphenylstibine

Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/N?)
Infobox references

Triphenylarsine is the chemical compound with the formula As(C6H5)3. This organoarsenic compound, often abbreviated AsPh3, is a colorless crystalline solid that is used as a ligand and a reagent in coordination chemistry and organic synthesis. The molecule is pyramidal with As-C distances of 1.942–1.956 Å and C-As-C angles of 99.6–100.5°.[1]

This compound is prepared by the reaction of arsenic trichloride with chlorobenzene using sodium as the reducing agent:[2]

AsCl3 + 3 PhCl + 6 Na → AsPh3 + 6 NaCl

Uses[edit]

AsPh3 is the precursor to tetraphenylarsonium chloride, [AsPh4]Cl, a popular precipitating agent.[2]

AsPh3 forms complexes with low valent metals that are analogous to the corresponding triphenylphosphine derivatives, such as IrCl(CO)(AsPh3)2 and RhCl(AsPh3)3.

References[edit]

  1. ^ Mazhar-ul-Haque, Hasan A. Tayim, Jamil Ahmed, and William Horne "Crystal and molecular structure of triphenylarsine" Journal of Chemical Crystallography Volume 15, Number 6 / 1985. doi: 10.1007/BF01164771
  2. ^ a b Shriner, R. L.; Wolf, C. N. (1963), "Tetraphenylarsonium Chloride Hydrochloride", Org. Synth. ; Coll. Vol. 4: 910  article