A Manual of the Chemistry of the Carbon Compounds

338 THE OMBMISTRT OF
HALOID SUBSTITUTION-PRODUCTS OF PHENOL.
OrOwMwophmol C0H4Cl.OH is the first product of the action of
chlorine on phenoL It crystallizes in white needles, melting at 41°,
and boiling at 218°. It possesses a faint but very disagreeable smell,
and is very caustic, producing white blisters on the skin. An isomeric
compound has been obtained from the second diazo-compound, as
above mentioned. It is a thick oily liquid, having a peculiar aromatic
odour, and boiling at about 180°.
Dichlorophenol CjHg -I ^g is obtained, together with trichloro-
phenol, by the action of chlorine on phenol or chlorophenol. To
separate the two compounds, the mixture is treated with a warm
solution of sodium carbonate, by which only the tricblorophenol is
dissolved, whilst impure dichlorophenol is left behind as an oily liquid,
which is purified by fractional distillation and recrystallization. It
crystallizes from benzene in long needles, melting at 43°, and boiling
at 209°,
Tricfdoroplienol C0Hg| Q& crystallizes in thin white needles,
melting li at t 61°, 61° and d boiling bili at t 244° 244°. It possesses a strong, t disagree- di
able odour, and is a monobasic acid,
Tetraehlarophcnol C8H •! QA- is not known-in a pure state.
PcntacMorophenol or PerehUrrophmol (LC16.OH is readily obtained
by the action of chlorine on a mixture ot phenol and antimony trichloride..
The crude product is purified by distilling it with steam
at 180°—200°. It crystallizes from petroleum-naphtha in thin, long,
brilliant needles, melting at 187°; its alcoholic solution colours blue
litmus red. At the common temperature it is .odourless, but when
heated it gives off a very pungent odour, and its dust produces violent
sneezing. Phosphorus pentaehloride converts it into hexachlorofcenzene.
When its potassium salt is heated, it is resolved into
potassium chloride and pcrchlorophmylene oxide CpCl.O, which is
insoluble in alcohol and most other solvents, but dissolves freely in
boiling nitrobenzene, and crystallizes on cooling in fiat needles, resembling
benzoic acid. It melts at 320°, and boils above the boilingpint
oi' mercury. As this compound has such a high boiling-point,
it has probably the following constitution:—
COC1
f Br
Monobromophenol C6H4 < QTT is obtained by dissolving bromine aud
phenol in glacial acetic acid, and gradually mixing the well-cooled