Tetraphenylarsonium chloride is the
organoarsenic compound
Organoarsenic chemistry is the chemistry of compounds containing a chemical bond between arsenic and carbon. A few organoarsenic compounds, also called "organoarsenicals," are produced industrially with uses as insecticides, herbicides, and fungic ...
with the formula (C
6H
5)
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
Triphenylarsine is the chemical compound with the formula As(C6H5)3. This organoarsenic compound, often abbreviated As Ph3, is a colorless crystalline solid that is used as a ligand and a reagent in coordination chemistry and organic synthesis. The ...
:
:(C
6H
5)
3As + Br
2 → (C
6H
5)
3AsBr
2
:(C
6H
5)
3AsBr
2 + H
2O → (C
6H
5)
3AsO + 2 HBr
: (C
6H
5)
3AsO + C
6H
5MgBr → (C
6H
5)
4AsOMgBr
:(C
6H
5)
4AsOMgBr + 3 HCl → (C
6H
5)
4AsCl
.HCl + MgBrCl
:(C
6H
5)
4AsCl
.HCl + NaOH → (C
6H
5)
4AsCl + NaCl + H
2O
Like other quat salts, it is used to solubilize polyatomic anions in organic media.
[{{cite book , doi=10.1002/9780470132470.ch36, chapter=Tetraethylammonium, Tetraphenylarsonium, and Ammonium Cyanates and Cyanides, year=1976, volume=16, last1=Dieck, first1=R. L., last2=Peterson, first2=E. J., last3=Galliart, first3=A., last4=Brown, first4=T. M., last5=Moeller, first5=T., title=Inorganic Syntheses, series=Inorganic Syntheses, pages=131–137, isbn=9780470132470] 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
*
Tetraphenylphosphonium chloride
Tetraphenylphosphonium chloride is the chemical compound with the formula (C6H5)4PCl, abbreviated Ph4PCl or PPh4Cl. Tetraphenylphosphonium and especially tetraphenylarsonium salts were formerly of interest in gravimetric analysis of perchlorate an ...
*
Tetrabutylammonium chloride
Tetrabutylammonium chloride is the organic compound with the formula (C4H9)4NCl. A white water-soluble solid, it is a quaternary ammonium salt of chloride. It is a precursor to other tetrabutylammonium salts. Often tetrabutylammonium bromide
...
*
Tetraethylammonium chloride
Tetraethylammonium chloride (TEAC) is a quaternary ammonium compound with the chemical formula (C2H5)4N+Cl−, sometimes written as Et4N+Cl−. In appearance, it is a hygroscopic, colorless, crystalline solid. It has been used as the source of tet ...
References
Chlorides
Phenyl compounds