Triphenylarsine

Triphenylarsine
IUPAC name Triphenylarsane
Other names Tribenzenidoarsenic Triphenylarsine
Identifiers
CAS number	603-32-7 Y
PubChem	11773
ChemSpider	11280 Y
EC number	210-032-9
UN number	3465
RTECS number	CH8942500
Jmol-3D images	Image 1 Image 2
SMILES C1=CC=C(C=C1)[As](C1=CC=CC=C1)C1=CC=CC=C1 c1ccc(cc1)[As](c2ccccc2)c3ccccc3
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
Properties
Molecular formula	C18H15As
Molar mass	306.23 g mol−1
Exact mass	306.038971897 g mol-1
Appearance	Colourless solid
Density	1.395 g cm-3
Melting point	58-61 °C, 331-334 K, 136-142 °F
Boiling point	175 °C, 448 K, 347 °F (at 1.5 mmHg)
Structure
Crystal structure	Triclinic
Hazards
EU classification	T N
R-phrases	R23/25, R50/53
S-phrases	S20/21, S28, S45, S60, S61
Related compounds
Related organoarsanes	Trimethylarsine
Related compounds	Triphenylamine Triphenylborane Triphenylphosphine Triphenylstibine
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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 reaction of arsenic trichloride with chlorobenzene using sodium as the reducing agent:^[2]

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

Uses

AsPh₃ is the precursor to tetraphenylarsonium chloride, [AsPh₄]Cl, a popular precipitating agent.^[2]

AsPh₃ forms complexes with low valent metals that are analogous to the corresponding triphenylphosphine derivatives, such as IrCl(CO)(AsPh₃)₂ and RhCl(AsPh₃)₃.

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", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv4p0910 ; Coll. Vol. 4: 910