M. Cloez on Benzoic Compounds. 283 
assay flask, carbonic acid is given off, and chloride of potassium 
formed, with which remains associated a new body, cyaphenine. 
Some benzonitryle is formed at the same time. Cyaphenine is 
volatile without decomposition, and may therefore be separated 
from the chloride by heat; or the chloride may be dissolved out 
by water. 
Cyaphenine has the formula C42H!5.N8; it corresponds to 
cyanethine, C'® H N3, discovered by Frankland and Kolbe. 
The latter body may be regarded as a triple molecule of cyanide 
of ethyle, C’ HH" N8=38(C4 H°C?N); so cyanethine may be 
considered as a triple molecule of benzonitrile or cyanide of phe- 
nyle, C4? H!§ N?=3(C”? HP C2N). The formation of cyaphe- 
nine may be thus expressed :— 
304 H5 02, C1+3KO, C7 NO=C* HH N84 3KC1+46CO*. 
Chloride of Cyanate of Cyaphenine. 
benzoyle. potash. 
Cyaphenine is a neutral, solid, hard substance, with a crystal- 
line fracture ; it fuses at 224°, and distils at 350°. It is little 
soluble in absolute alcohol. Potash decomposes it, liberating 
ammonia. Treated by strong nitric acid it yields a crystallized 
nitro-compound, C4? H!? (NO*)? N®. 
Thiobenzoic Acid, O4 H5 02S, HS.—This body corresponds to 
thioacetic acid, obtained by Kekulé by the action of pentasul- 
phide of phosphorus on acetic acid. It is prepared by adding 
chloride of benzoyle to an alcoholic solution of hydrosulphide of 
potassium. It crystallizes from bisulphide of carbon in rhomb- 
oidal plates. When pure it is inodorous and tasteless. It fuses 
at 120°, and begins to decompose at about 160°—180°. It is 
not soluble in water, and but slightly so in alcohol and in ether. 
Its best solvents are sulphur compounds, such as mercaptan, 
sulphide of ethyle, and bisulphide of carbon. It combines with 
potash, soda, and ammonia to form definite crystallized salts, 
from which the acid is liberated unchanged on the addition of 
hydrochloric acid. 
Kekulé’s thiacetic acid has been obtained by Jaequemin and 
Vosselmann* by the gradual addition of chloride of acetyle to 
hydrosulphide of potassium. 
Carius, in a paper} on the equivalent substitution of oxygen 
by sulphur, describes several new sulphur compounds. 
The action of pentasulphide of phosphorus had been inter- 
preted by Kekulé as being analogous to that of pentachloride of 
* Comptes Rendus, vol. xlix. p. 371. 
+ Liebig’s Annalen, November 1859. 
