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
Ball and stick model of aromatic triphenylarsine
Names
Preferred IUPAC name
Triphenylarsane
Other names
Tribenzenidoarsenic
Triphenylarsine
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.009.121
EC Number
  • 210-032-9
RTECS number
  • CH8942500
UNII
UN number 3465
  • InChI=1S/C18H15As/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H checkY
    Key: BPLUKJNHPBNVQL-UHFFFAOYSA-N checkY
  • InChI=1/C18H15As/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H
    Key: BPLUKJNHPBNVQL-UHFFFAOYAO
  • C1=CC=C(C=C1)[As](C1=CC=CC=C1)C1=CC=CC=C1
  • c1ccc(cc1)[As](c2ccccc2)c3ccccc3
Properties
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
Insoluble
Solubility Soluble in ethyl ether, benzene, slightly soluble in ethanol
-177.0·10−6 cm3/mol
Structure
Triclinic
Hazards
GHS labelling:
GHS06: ToxicGHS09: Environmental hazard
Danger
H301, H331, H410
P261, P264, P270, P271, P273, P301+P310, P304+P340, P311, P321, P330, P391, P403+P233, P405, P501
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]

Tetraphenylarsonium chloride is prepared from triphenylarsine:[5]

(C6H5)3As + Br2 → (C6H5)3AsBr2
(C6H5)3AsBr2 + H2O → (C6H5)3AsO + 2 HBr
(C6H5)3AsO + C6H5MgBr → (C6H5)4AsOMgBr
(C6H5)4AsOMgBr + 3 HCl → (C6H5)4AsCl.HCl + MgBrCl
(C6H5)4AsCl.HCl + NaOH → (C6H5)4AsCl + NaCl + H2O

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.{{cite journal}}: CS1 maint: multiple names: authors list (link); Collective Volume, vol. 4, p. 910 article
  3. W. Levason; C. A. Mcauliffe (1976). "Cis -2-Diphenylarsinovinyldiphenylphosphine and 2-Diphenylarsinoethyldiphenylphosphine". cis-2-Diphenylarsinovinyldiphenylphosphine and 2-Diphenylarsinoethyldiphenylphosphine. Inorganic Syntheses. Vol. 16. pp. 188–192. doi:10.1002/9780470132470.ch50. ISBN 978-0-470-13247-0.
  4. C. A. McAuliffe, ed. (1973). Transition Metal Complexes of Phosphorus, Arsenic, and Antimony Ligands. J. Wiley. ISBN 0-470-58117-4.
  5. Shriner, R. L.; Wolf, Calvin N. (1950). "Tetraphenylarsonium Chloride Hydrochloride". Organic Syntheses. 30: 95. doi:10.15227/orgsyn.030.0095.
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