8058. Quinhydrone

Nomenclature

CAS number: 106-34-3
2,5-Cyclohexadiene-1,4-dione compd with 1,4-benzenediol (1:1); green hydroquinone.
C12H10O4; mol wt 218.21.
C 66.05%, H 4.62%, O 29.33%.

Description and references

An addn compd of one mol hydroquinone and one mol quinone. Prepn from hydroquinone and quinone: Gattermann-Wieland, Praxis des Organischen Chemikers (de Gruyter, Berlin, 40th ed., 1961) p 270. Alternate prepn by the action of ferric ammonium sulfate on hydroquinone: A. I. Vogel, Practical Organic Chemistry (Longmans, London, 3rd ed., 1959) p 747. Toxicity study: Woodward et al., Fed. Proc. 8, 348 (1949).

Chemical structure

Properties

Green crystals with metallic luster; reddish-brown by transmitted light. d 1.40. mp 171°; sublimes with partial decompn. Slightly sol in cold water; sol in hot water, ammonia, alc, ether. Insol in petr ether. LD50 orally in rats: 225 mg/kg (Woodward).

Use

In pH determinations (quinhydrone electrode).