JACKSON AND GALLIVAN. — TRIBROMANILINE. 51 



Properties. — This tribromnitraniline crystallizes from alcohol in yel- 

 lowish orange needles arranged in radiating groups. If the cooling is 

 rapid, little circular masses of needles are formed. It melts at 130° ; and 

 is easily soluble in alcohol, ether, benzol, or chloroform ; essentially 

 insoluble in ligroin, or in cold water, slightly soluble in boiling water. 



In the hope of converting the tribromnitraniline just described into a 

 tribromnitrobenzol, from which the vicinal tetrabrombenzol might be 

 obtained, we submitted it to the diazo reaction as follows. Fourteen 

 grams of the tribromnitraniline were dissolved in boiling alcohol pre- 

 viously acidified with sulphuric acid, and ten grams of powdered sodic 

 nitrite added in small portions at a time. The mixture was then boiled 

 for thirty minutes, and allowed to stand over night at ordinary tem[)era- 

 tures. Upon adding water a yellowish precipitate was formed, which, 

 after recrystallization from alcohol, melted at 230°. An analysis indi- 

 cated that the substance was the phenol CGHBrgNOoOH, although the 

 agreement between the percentage of bromine found and that calculated 

 left much to be desired. (Calculated per cent of bromine, 63.83. Found, 

 64.54.) Unfortunately, we did not have enough substance for more 

 thorough purification ; but its properties showed plainly that it was a 

 phenol, as it dissolved in a solution of sodic ethylate forming a reddish 

 brown salt, from which the original substance was recovered by acidifica- 

 tion. As, therefore, this line of work evidently would not lead to the 

 vicinal tetrabrombenzol, we did not think it worth while to undergo the 

 large amount of labor necessary to prepare more of this phenol in order 

 to characterize it more satisfactorily. 



Tribromphenylurethane, CeHoBrgNHCOOCaHs, NH 1, Brg 2, 4, 5. 



This substance was prepared in order to characterize more fully the 

 tribromaniline NII2I, Brg 2, 4, 5, described in our first paper.* Ten 

 grams of the tribromaniline dissolved in benzol were heated with eight 

 grams of chlorocarbonic ethyl ester in a flask with a return condenser, 

 until no more hydrochloric acid was given off. The product thus ob- 

 tained was crystallized from alcohol, until it showed the constant melting 

 point 101°, when it was dried, and analyzed with the following result: — 



0.1432 gram of the substance gave 0.2016 gram of argentic bromide 

 by the method of Carius. 



Calculated for CoH^BrgNIICOOCoIIs. Found. 



Bromine 59.70 59.92 



Amer. Cliem. Journ., XVIII. 247. 



