urbaf2

NITRO DERIVATIVES OF HALOGENOBENZENES 453

TABLE 102

SOLUBILITY OF 1-CHLORO-2,4-DINITROBENZENE

g/100 g of the solvent

Solvent

15°C 100°C

Water 0.0008 at 50°C 0.041 0.159

Methyl alcohol 11.226 at 32°C 32.31

Ethyl alcohol abs. 8.246 at 32.5°C 18.89

Ethyl ether 23.517 at 30.5°C 128.13

Acetone 261.9 at 30°C 581.0

Ethyl acetate 119.4 at 50°C 287.5

Chloroform 102.76 at 32°C 210.0

Carbon tetrachloride 3.851 at 31°C 28.87

Carbon disulphide 4.212

Benzene 158.43 at 31°C 359.64

Toluene 139.89 at 31.5°C 282.55

Pyridine 2.633 at 20°C 20.85

In sulphuric acid of concentrations below 80%, 1-chloro-2,4-dinitrobenzene

dissolves only with difficulty.

Chemical properties. A chlorine atom ortho or para to a nitro group is especially

reactive and is readily substituted. Numerous examples of such reactions, utilized

in the preparation of explosives, are given later in the descriptions of preparation

methods for dinitrophenol, dinitroanisole, hexanitrodiphenylamine, hexanitro-

diphenyl sulphone, dinitroaniline, tetryl, etc. Chlorodinitrobenzene reacts with

sodium sulphide and sulphur to yield sulphur dyes. The action of sodium disulphide

results in the formation of tetranitrodiphenyl sulphide (p. 554).

When treated with KHS in alcoholic solution chlorodinitrobenzene

dinitrothiophenol :

yields

(2)

the reaction being of the nucleophilic substitution type.

Chlorodinitrobenzene reacts with pyridine to form dinitrophenylpyridinium
chloride (Vongerichten [19]):