Triphenylarsine

Triphenylarsine
Names
IUPAC name
Triphenylarsane
Other names
Tribenzenidoarsenic
Triphenylarsine
Identifiers
603-32-7 YesY
ChemSpider 11280 YesY
EC Number 210-032-9
Jmol interactive 3D Image
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PubChem 11773
RTECS number CH8942500
UN number 3465
Properties
C18H15As
Molar mass 306.24 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
Insoluble
Solubility Soluble in ethyl ether, benzene, slightly soluble in ethanol
Structure
Triclinic
Hazards
T 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 otherwise noted, data are 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

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

  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. 1 2 Shriner, R. L.; Wolf, C. N. (1963). "Tetraphenylarsonium Chloride Hydrochloride". Org. Synth.; Coll. Vol. 4, p. 910 article
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