Triphenylarsine

Triphenylarsine
Names
	IUPAC name Triphenylarsane
	Other names Tribenzenidoarsenic; Triphenylarsine
Identifiers
CAS Number	603-32-7 ;
3D model (JSmol)	Interactive image; Interactive image;
ChemSpider	11280 ;
ECHA InfoCard	100.009.121
EC Number	210-032-9;
PubChem CID	11773;
RTECS number	CH8942500;
UNII	MN8EZ3FL74 ;
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 Key: BPLUKJNHPBNVQL-UHFFFAOYSA-N ; 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 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EU classification (DSD) (outdated)	T N
R-phrases (outdated)	R23/25, R50/53
S-phrases (outdated)	S20/21, S28, S45, S60, S61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).

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

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

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

[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

[Shriner-2] Shriner, R. L.; Wolf, C. N. (1963). "Tetraphenylarsonium Chloride Hydrochloride". Organic Syntheses.; Collective Volume, 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. 16. pp. 188–192. doi:10.1002/9780470132470.ch50. ISBN 9780470132470.

[McAuliffe-4] C. A. McAuliffe, ed. (1973). Transition Metal Complexes of Phosphorus, Arsenic, and Antimony Ligands. J. Wiley. ISBN 0-470-58117-4.

[1]

[2]

[3]

[4]

Names


IUPAC name Triphenylarsane
Other names Tribenzenidoarsenic Triphenylarsine
Identifiers
CAS Number	603-32-7
3D model (JSmol)	Interactive image Interactive image
ChemSpider	11280
ECHA InfoCard	100.009.121
EC Number	210-032-9
PubChem CID	11773
RTECS number	CH8942500
UNII	MN8EZ3FL74
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 Key: BPLUKJNHPBNVQL-UHFFFAOYSA-N 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 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).