A Manual of the Chemistry of the Carbon Compounds

444 THE CHEMISTRY OF
HYDE0-ANTHBACENE8.
DUiydro-anthraeene C,,H,2.—Whilst phenanthrene and naphthalene
are not changed by boiling their alcoholic solutions with sodiumamalgam,
anthracene is, under these conditions, converted into
dihydro-anthracene. It is readily soluble in alcohol, and crystallizes
in nionoclinic plates, melting at 106°, and boiling at 305°, but subliming
at a lower temperature in brilliant needles. When heated to
a dull-red heat, it is resolved into anthracene and hydrogen.
ffexaliydro-anthracene Cj4H,a is obtained by heating dihydroanthracene
with fuming hydriodic acid and amorphous phosphorus to
200°. It dissolves freely in alcohol, and crystallizes in small plates,
melting at 63°, and boiling at 290°. At a red-heat it is decomposed
into hydrogen and anthracene.
The constitution of these hydrides is explained by the following
graphical formula :—
Dihydro-anthraoeno. Hexaliydro-antliraconn.
CH CH2 CH CH CH2 CH
H / V V X C H /
HC C C CH HC CH CH CH
CHLORINE AND BROMINE DERIVATIVES.
Anthracene DicMoride CMH1OC1? is obtained by passing chlorine
slowly over anthracene; it crystallizes from alcohol in long needles.
MonocUoranthracene CUH8C1 ia produced afc the same time, and
readily obtained by heating the dichloride with alcoholic potash; it
crystallizes in hard scales.
Dichloranthracme C^HgOL—By passing chlorine over heated
anthracene, higher chlorinated products are formed. Dicliloranfchracene
is sparingly soluble in alcohol, but freely in benzene. It crystallizes
in long yellow needles, melting at 209°; its solutions exhibit
a splendid blue fluorescence.
Tetrachlomntkraeene CyHgC^ i3 but sparingly soluble ia alcohol,
and crystallizes from benzene in yellow needles.
JHbromanthracene CuH.Br? is the only compound formed when
bromine is added to a solution of anthracene in carbon disulphide.
It orystallize84K>in petroleum-naphtha in golden-yellow needles, and
can be sublimed.
DHyroinanthraBem Telrabromide CwH8Br8 is formed when the preceding
compound is exposed to gaseous bromine, and crystallizes
X
^