Triphenylarsine

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Triphenylarsine
Ball and stick model of aromatic triphenylarsine
Names
IUPAC name
Triphenylarsane
Other names
Tribenzenidoarsenic
Triphenylarsine
Identifiers
603-32-7 YesY
ChemSpider 11280 YesY
EC number 210-032-9
Jmol-3D images Image
Image
PubChem 11773
RTECS number CH8942500
UN number 3465
Properties
C18H15As
Molar mass 306.23 g·mol−1
Appearance Colourless solid
Density 1.395 g cm−3
Melting point 58 °C (136 °F; 331 K)
Boiling point 373 °C (703 °F; 646 K) at 760 mmHg
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 is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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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, p. 910  article