Triphenylarsine

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]

Triphenylarsine
Names
IUPAC name
Triphenylarsane
Other names
Tribenzenidoarsenic
Triphenylarsine
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.009.121
EC Number
  • 210-032-9
PubChem CID
RTECS number
  • CH8942500
UNII
UN number 3465
CompTox Dashboard (EPA)
Properties
Chemical formula
 C18H15As
Molar mass 306.240 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
Magnetic susceptibility (χ)
 -177.0·10−6 cm3/mol
Structure
Crystal structure
 Triclinic
Hazards
EU classification (DSD) (outdated)
 T N
R-phrases (outdated) R23/25, R50/53
S-phrases (outdated) S20/21, S28, S45, S60, S61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

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

Reactions

Reaction of triphenylarsine with lithium gives lithium diphenylarsenide:[3]

AsPh3 + 2 Li → LiAsPh2 + LiPh

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

AsPh3 forms metal complexes with metals. Most are analogues of the corresponding triphenylphosphine derivatives. Examples include IrCl(CO)(AsPh3)2, RhCl(AsPh3)3, and Fe(CO)4(AsPh3).[4]

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. Shriner, R. L.; Wolf, C. N. (1963). "Tetraphenylarsonium Chloride Hydrochloride". Organic Syntheses.CS1 maint: multiple names: authors list (link); Collective Volume, 4, p. 910 article
  3. W. Levason, C. A. Mcauliffe (1976). "cis‐2‐Diphenylarsinovinyldiphenylphosphine and 2‐Diphenylarsinoethyldiphenylphosphine". Inorganic Syntheses. 16: 188–192. doi:10.1002/9780470132470.ch50.CS1 maint: uses authors parameter (link)
  4. C. A. McAuliffe, ed. (1973). Transition Metal Complexes of Phosphorus, Arsenic, and Antimony Ligands. J. Wiley. ISBN 0-470-58117-4.
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