Triphenylarsine

Triphenylarsine
	Ball and stick model of aromatic triphenylarsine
Names
	Preferred 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
	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). verify (what is ?) 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]

Preparation

Triphenylarsine is prepared by treating phenyl lithium with arsenic tribromide. The method can be used to prepare many analogues with diverse aryl groups.^[2]

Triphenylarsine can also be prepared by the Wurtz-like reaction of arsenic trichloride with chlorobenzene using sodium as the reducing agent:^[3]

AsCl₃ + 3 PhCl + 6 Na → AsPh₃ + 6 NaCl

Reactions

Reaction of triphenylarsine with lithium gives lithium diphenylarsenide and phenyllithium:^[4]

AsPh₃ + 2 Li → LiAsPh₂ + LiPh

Triphenylarsine is the precursor to tetraphenylarsonium chloride, [AsPh₄]Cl, a popular precipitating agent.^[3]

Many metal-arsine complexes have been prepared using AsPh₃. Examples include IrCl(CO)(AsPh₃)₂, RhCl(AsPh₃)₃, and Fe(CO)₄(AsPh₃).^[5]

Treatment of triphenylarsine with hydrogen peroxide gives triphenylarsine oxide: ^[6]

AsPh₃ + H₂O₂ → OAsPh₃ + H₂O

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
^ Tanaka, Susumu; Konishi, Masafumi; Imoto, Hiroaki; Nakamura, Yuma; Ishida, Masatoshi; Furuta, Hiroyuki; Naka, Kensuke (2020). "Fundamental Study on Arsenic(III) Halides (AsX₃; X = Br, I) toward the Construction of C₃-Symmetrical Monodentate Arsenic Ligands". Inorganic Chemistry. 59 (14): 9587–9593. doi:10.1021/acs.inorgchem.0c00598. PMID 32515950.
^ ^a ^b Shriner, R. L.; Wolf, Calvin N. (1950). "Tetraphenylarsonium Chloride Hydrochloride". Organic Syntheses. 30: 95. doi:10.15227/orgsyn.030.0095.
^ 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.
^ C. A. McAuliffe, ed. (1973). Transition Metal Complexes of Phosphorus, Arsenic, and Antimony Ligands. J. Wiley. ISBN 0-470-58117-4.
^ Mollat Du Jourdin, Xavier (2015). "Triphenylarsine Oxide". Encyclopedia of Reagents for Organic Synthesis. pp. 1–3. doi:10.1002/047084289X.rn01860. ISBN 978-0-470-84289-8.

[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

[Tanaka-2] Tanaka, Susumu; Konishi, Masafumi; Imoto, Hiroaki; Nakamura, Yuma; Ishida, Masatoshi; Furuta, Hiroyuki; Naka, Kensuke (2020). "Fundamental Study on Arsenic(III) Halides (AsX₃; X = Br, I) toward the Construction of C₃-Symmetrical Monodentate Arsenic Ligands". Inorganic Chemistry. 59 (14): 9587–9593. doi:10.1021/acs.inorgchem.0c00598. PMID 32515950.

[Shriner-3] Shriner, R. L.; Wolf, Calvin N. (1950). "Tetraphenylarsonium Chloride Hydrochloride". Organic Syntheses. 30: 95. doi:10.15227/orgsyn.030.0095.

[4] 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.

[McAuliffe-5] C. A. McAuliffe, ed. (1973). Transition Metal Complexes of Phosphorus, Arsenic, and Antimony Ligands. J. Wiley. ISBN 0-470-58117-4.

[6] Mollat Du Jourdin, Xavier (2015). "Triphenylarsine Oxide". Encyclopedia of Reagents for Organic Synthesis. pp. 1–3. doi:10.1002/047084289X.rn01860. ISBN 978-0-470-84289-8.

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