306 PROCEEDINGS OF THE AMERICAN ACADEMY 



der white needles forming a thick mat. It turns yellowish brown 

 on exposure to the air, and melts at 171° ; is slightly soluble even 

 in hot alcohol, less soluble still in cold; somewhat more soluble in 

 methyl than in ethyl alcohol; very freely soluble in benzol, chloro- 

 form, or acetone; freely in carbonic disulphide; soluble in glacial 

 acetic acid; very slightly soluble in ligroine; essentially insoluble 

 in water, whether cold or hot. The best solvent for it is a mixture 

 of alcohol and benzol. Strong sulphuric acid does not seem to act 

 on it until charring sets in ; strong nitric acid does not act on it 

 in the cold, but seems to oxidize it when hot; strong hydrochloric 

 acid has no apparent action on it, hot or cold. 



Other Products of the Action of Sodic Benzylate on Tribromtri- 

 nltrobenzol. — To obtain these substances the aqueous and alcoholic 

 washings mentioned above were evaporated to dryness, and the oil}' 

 portion separated by extraction with a little alcohol from the salts. 

 These, it was found, w r ere a mixture of the sodium salt of trinitro- 

 phloroglucine with sodic bromide and nitrite, from which the trini- 

 trophloroglucine was easily obtained, and identified by the melting 

 point 167°, and by analysis. It is one of the principal products of 

 the reaction, and in fact most of the trinitrophloroglucine used for 

 the analyses given in the first part of this paper was obtained in 

 this way. 



The oily material separated by the alcohol consisted mostly of 

 the excess of benzyl alcohol, but on warming it we perceived the 

 smell of benzyl bromide, and also suffered from its violent action on 

 the eyes. Accordingly some of it, carefully washed to remove any 

 sodic bromide, was boiled with an alcoholic solution of sodic sul- 

 phide, when it gave a strong smell of benzyl sulphide, and the 

 water with which it was washed gave a faint test for bromine with 

 chlorine water. We did not succeed, however, in isolating the 

 benzyl sulphide, which at best must have been present in very small 

 quantity. Another similar oil, after thorough washing with water, 

 was boiled with sodic acetate and alcohol, then water was added, 

 which after being freed from the organic matter gave a slight test for 

 bromine with chlorine water. In another experiment the original 

 product, after acidification with dilute sulphuric acid, was distilled 

 with steam, and the oily distillate, having been thoroughly washed 

 with water, was boiled with alcoholic sodic acetate, when it yielded 

 a very strong test for a bromide with chlorine water. These exper- 

 iments have convinced us that in these three preparations a small 

 quantity of benzyl bromide was present in the product of the reac- 



