Triphenylarsine

Triphenylarsine

Names
Preferred IUPAC name Triphenylarsane
Other names Tribenzenidoarsenic Triphenylarsine
Identifiers
CAS Number	603-32-7^Y
3D model (JSmol)	Interactive image Interactive image
ChemSpider	11280^Y
ECHA InfoCard	100.009.121
EC Number	210-032-9
PubChem CID	11773
RTECS number	CH8942500
UNII	MN8EZ3FL74^Y
UN number	3465
CompTox Dashboard (EPA)	DTXSID4060529
InChI 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^Y Key: BPLUKJNHPBNVQL-UHFFFAOYSA-N^Y 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
SMILES C1=CC=C(C=C1)[As](C1=CC=CC=C1)C1=CC=CC=C1 c1ccc(cc1)[As](c2ccccc2)c3ccccc3
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 cm^3/mol
Structure
Crystal structure	Triclinic
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301, H331, H410
Precautionary statements	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). Y verify (what is ^YN ?) 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 Wurtz 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 and phenyllithium:^[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; Collected Volumes, 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.