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Tetraphenylarsonium chloride

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Tetraphenylarsonium chloride
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.337 Edit this at Wikidata
EC Number
  • 208-070-6
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C24H20As.ClH/c1-5-13-21(14-6-1)25(22-15-7-2-8-16-22,23-17-9-3-10-18-23)24-19-11-4-12-20-24;/h1-20H;1H/q+1;/p-1Key: NRZGVGVFPHPXEO-UHFFFAOYSA-M
SMILES
  • C1=CC=C(C=C1)(C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4.
Properties
Chemical formula C24H20AsCl
Molar mass 418.80 g·mol
Appearance white solid
Hazards
GHS labelling:
Pictograms GHS06: ToxicGHS09: Environmental hazard
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
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Tetraphenylarsonium chloride is the organoarsenic compound with the formula (C6H5)4AsCl. This white solid is the chloride salt of the tetraphenylarsonium cation, which is tetrahedral. Typical of related quat salts, it is soluble in polar organic solvents. It often is used as a hydrate.

Synthesis and reactions

It is prepared by neutralization of tetraphenylarsonium chloride hydrochloride, which is produced from triphenylarsine:

(C6H5)3As + Br2 → (C6H5)3AsBr2
(C6H5)3AsBr2 + H2O → (C6H5)3AsO + 2 HBr
(C6H5)3AsO + C6H5MgBr → (C6H5)4AsOMgBr
(C6H5)4AsOMgBr + 3 HCl → (C6H5)4AsClHCl + MgBrCl
(C6H5)4AsClHCl + NaOH → (C6H5)4AsCl + NaCl + H2O

Like other quat salts, it is used to solubilize polyatomic anions in organic media. To this end, aqueous or methanolic solutions containing the anion of interest are treated with a solution of tetraphenylarsonium chloride, typically resulting in precipitation of the tetraphenylarsonium anion salt.

Related compounds

References

  1. Shriner, R. L.; Wolf, Calvin N. (1950). "Tetraphenylarsonium Chloride Hydrochloride". Organic Syntheses. 30: 95. doi:10.15227/orgsyn.030.0095.
  2. Dieck, R. L.; Peterson, E. J.; Galliart, A.; Brown, T. M.; Moeller, T. (1976). "Tetraethylammonium, Tetraphenylarsonium, and Ammonium Cyanates and Cyanides". Inorganic Syntheses. Vol. 16. pp. 131–137. doi:10.1002/9780470132470.ch36. ISBN 9780470132470.
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