A Manual of the Chemistry of the Carbon Compounds

THE OARBON COMPOUNDS. 325
of these two compounds is most probably caused by two phenyl groups
replacing different atoms of hydrogen in guanidine C(NHXNH,L
(hrMnphenyHriamme or tHjphmyl-guanidine C(NH) \ ^Jn g \ 5
is a mon-acid base, which is formed by the action of tetracnloromethane
CC14 on aniline. It is a crystalline solid, insoluble in
water, and forming crystallized salts.
CyanUine C?(NH)g(NH.C0H5}.—On passing cyanogen gas into an
alcoholic solution of aniline, this compound separates out after some
tiraa It is a crystalline solid, combining with acids. On heating it
with aqueous acids, it is decomposed with formation of rnnmonia, and
oxanilide or oxamide:—
NH.C6H6
NH.CaH5
O.NH CO
| + 2H2O - F + 2NHS
C.NH CO
NH.CA NH.C
Cyaiwbenzcne or Phenyl Uarlamine CN.C?H5.—This compound is
obtained by the distillation of a mixture ot aniline, chloroform, and
caustic potash. It is liquid, boiling, with partial decomposition, at
160°. Its colour appears blue in reflected light, and green by transmitted
light. It has a most penetrating odour, like other carbarn ines.
By acids it is decomposed with the formation of aniline and formic
acid.
SUBSTITUTED ANII^ES.
Monochloranilinc C6H4CLNH« is prepared by acting with strong
nitric acid on chlorobenzene, ana treating the nitrochlorobeuzene thus
formed with a reducing agent. Mouoclilomniline is insoluble in cold
water, very sparingly soluble in boiling water, but readily in alcohol.
It crystallizes in shining octahedrons, and is a weak base, forming
crystalline salts.
Dichhraniline C6H3Clj.NH4 and tritHiloraniline COH3C1.NH8 are
crystalline solids, having no basic properties. Triclilomniline is also
formed, together with small quantities of the two other chloranilines,
by the aetion of chlorine upon aniline, the greatest part of which, however,
is converted into a dark tarry mass.
Monobromanilinc CjH^Br.NHa has been obtained from monobrombenzene,
and has great resemblance with chloranilinc.
Dibrom- and tribromauiline are produced by the action of bromine
upon aniline, as well as by heating nitrobenzene with hydrobromic
acid:—
C0H6.NO2 + CHBr = CflH6.NH, + 3Br8 + 2H8O