Triphenylarsine

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 Edit this at Wikidata
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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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. ^ a b Shriner, R. L.; Wolf, C. N. (1963). "Tetraphenylarsonium Chloride Hydrochloride". Organic Syntheses{{cite journal}}: CS1 maint: multiple names: authors list (link); 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.

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