JACKSON AND CALVERT. METAPHENYLENE DIAMINE. 155 



separated from the oil was shaken with ether repeatedly, and the oil 

 thus obtained added to the main portion. The aqueous solution after 

 shaking with ether gave a very slight precipitate on the addition of 

 bromine, but the amount of tetrabromphenylene diamine obtained in 

 this way was so small that this treatment is hardly worth while. The 

 principal product, after it had solidified, was purified by dissolving is 

 in rather dilute alcohol and saturating the solution witli suphuretted 

 hydrogen, when it was warmed gently, and allowed to stand in a 

 corked flask for some time ; after filtering off the sulphide of tin it 

 was evaporated to dryness, and the residue recrystallized from pure 

 ligroine (boiling from 60°-70°) until it showed the constant melting 

 point 93° -94°, when it was dried in a desiccator and analyzed with 

 the following result : — 



0.2117 gram of the base gave by the method of Carius 0.2113 gram of 

 argentic bromide. 



Calculated for 



C6H3Br(NH2)2. Found. 



Bromine 42.79 42.48 



Properties of 3TonohrommetaphenyIene Diamine. It crystallizes from 

 a mixture of benzol and ligroine in white spindle-shaped forms often a 

 centimeter long ; from benzol alone in bundles of small needles united 

 longitudinally ; from alcohol in not very well developed prisms appar- 

 ently belonging to the monoclinic system and often twinned. It melts 

 at 93°-94°, and is readily soluble in acetone, alcohol, ether, or chloro- 

 form ; in benzol, or carbonic disulphide it is slightly soluble in the cold, 

 more freely when hot ; nearly insoluble in cold ligroine, difficultly solu- 

 ble in hot ; it is moderately soluble in cold water, as shown by the fact 

 that such a solution gives a good precipitate with bromine water ; in hot 

 water it is even more soluble, the solution as it cools depositing oil drops, 

 which later change to needles. The best solvent for it is a mixture 

 of benzol and ligroine, but crystallization from pure ligroine is neces- 

 sary to get a perfectly white product. It shows a tendency to separate 

 from its solutions at first as an oil, and also to become decomposed, 

 when in solution, forming a brown product. 



The monobromphenylene diamine shows marked basic properties. 

 Hydrochloric acid or hydrobromic acid gives with it a salt soluble in 

 water, a description and analysis of the bromide formed in this way is 

 given below; moderately strong sulphuric acid also gives a soluble salt, 

 which forms white crystals when the solution is allowed to evaporate 

 spontaneously ; dilute nitric acid seems to have little action on it in the 

 cold, but when hot converted it into a brown substance. Sodic hydrate 



