142 PROCEEDINGS OF THE AMERICAN ACADEMY. 



properties of the phenylene diamine ; but still it is jwssible to prepare 

 salts of our substance, if proper precautions are observed, and the 

 chloride is described somewhat later in this paper. Potassic hydrate, 

 even when a boiling concentrated solution was used, produced no 

 effect upon it. 



When the tribromphenylene diamine is treated with tin and hydro- 

 chloric acid it is converted into phenylene diamine. The details of 

 this work are given later in this paper. The success of this experi- 

 ment suggested to us that the bromine might be removed also by other 

 reagents ; accordingly we heated some tribromphenylene diamine dis- 

 solved in benzol and alcohol with sodic ethylate, the action in one trial 

 being continued for four days, but at the end of this time we recovered 

 nearly the whole of the tribromphenylene diamine taken, and although 

 the filtrate after treatment with nitric acid and argentic nitrate gave a 

 slight precipitate, we ascribe this rather to tlie complete decomposi- 

 tion of a small portion of the substance (indicated by the dark brown 

 color of the product) than to any simple reaction. As therefore sodic 

 ethylate had no action, it did not seem to us worth while to try other 

 experiments with less energetic reagents. 



Chloride of Tribromphenylene Diamine CcHBr3NH3ClNIl2. Al- 

 though the tribromphenylene diamine forms no salts under ordinary 

 conditions, we hoped that we might obtain its chloride by the method 

 which yielded such excellent results to Gattermann * when he applied 

 it to the tribromaniline. Acconlingly hydrochloric acid g.is was passed 

 into a solution of tribromphenylene diamine in benzol, until it ceased 

 to form a white precipitate, and the liquid fumed strongly. The 

 precipitate was then filtered out, and dried by pressing between filter 

 paper as quickly as possible, after which it was analyzed as follows : — 

 0.3096 gram of the salt lost 0.0272 gram of hydrochloric acid at 100°. 



Calculated for 

 CeHBrsNHsClNtlj. Found. 



Hydrochloric Acid 9.5 G 8.79 



The residue was entirely free from hydrochloric acid. This result 

 is not so near the theoretical percentage as could be wished, but never- 

 theless proves that the salt is a monochloride of tribromphenylene dia- 

 mine. The poor result is undoubtedly to be ascribed to the instability 

 of the compound, which lost as much as 3.3 per cent of its weight from 

 standing four days in a desiccator over sulphuric acid, and therefore 

 might well have lost the 0.77 of one per cent during the drying on 



* Ber. d. ch. G., XVI. 636. 



