JACKSON AND CALVERT. — METAPHENYLENE DIAMINE. 143 



filter paper. The chloride as obtained was of a light brown color, 

 although it is probably white when perfectly pure, and as indicated 

 by the description of its analysis is very unstable, decomposing slowly 

 in dry air at ordinary temperatures, quickly and completely when 

 heated to 100°. We should judge that it was somewhat more stable 

 than the chloride of tribromaniline prepared by Gattermann,* as might 

 be expected from the presence of the second amido group. It seems tp 

 be soluble in strong hydrochloric acid since the tribromphenylene dia- 

 mine dissolves in this reagent, but it is decomposed by water. 



Tribromphenylene Diacetamide, C6HBr.;(NHC2H30)2. This sub- 

 stance was made by treating tribromphenylene diamine with acetyl 

 chloride, using anhydrous benzol as a solvent. The action began even 

 in the cold as shown by the deposition of a white precipitate, but to 

 make certain that it was complete the mixture was heated under a 

 return-condenser for one hour. At the end of this time the white 

 sandy precipitate was filtered out, and purified by extraction with 

 glacial acetic acid, followed by recrystallization from the same sol- 

 vent boiling. It was dried at 100°, and analyzed with the following 

 results : — 

 I. 0.2726 gram of the substance gave 0.3561 gram of argentic bromide 



by the method of Carius. 

 II. 0.2548 gram of substance gave 0.3358 gram of argentic bromide. 



Bromine 



Properties. The tribromphenylene diacetamide crytallizes from hot 

 glacial acetic acid in bunches of small white plates much longer than 

 they are broad, which have square ends and frequently radiate from 

 a centre; from alcohol in radiating groups of compound crystals made 

 up of needles united longitudinally. It does not melt at 330°, and is 

 very slightly soluble in all the common solvents. The best solvent 

 for it is hot glacial acetic acid, but it is far from freely soluble even 

 in this. 



Trihromphenylene Diur ethane, C6HBr3(NHCOOC2H5)2. Five grams 

 of tribromphenylene diamine were boiled with about twice the amount 

 of chlorocarbonic ester required by the theory in a flask with a return 

 condenser for three hours. The crude product (which weighed 6.5 

 grams), was purified at first by precipitating the substance with ligroine 

 from its solution in a mixture of benzol and alcohol, afterward by 



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



