Tetraphenylarsonium chloride

Tetraphenylarsonium chloride
Identifiers
CAS Number	507-28-8 ;
3D model (JSmol)	Interactive image;
ChemSpider	61486;
ECHA InfoCard	100.007.337
EC Number	208-070-6;
PubChem CID	68179;
UNII	AG51MKF20J;
CompTox Dashboard (EPA)	DTXSID20964938 ;
	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-1 Key: NRZGVGVFPHPXEO-UHFFFAOYSA-M;
	SMILES C1=CC=C(C=C1)[As+](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4.[Cl-];
Properties
Chemical formula	C24H20AsCl
Molar mass	418.80 g·mol−1
Appearance	white solid
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
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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:^[1]

(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

Like other quat salts, it is used to solubilize polyatomic anions in organic media.^[2] 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

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

[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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