46 PROCEEDINGS OP THE AMERICAN ACADEMY. 



attempts to make vicinal tetrabrombenzol, and also a few corrections 

 and additions to our paper on "• On Some Derivatives of Unsymmetrical 

 Tribrombenzol " * published somewhat more than a year ago. 



3, 4, 5 Tribromaniline, CeHoBrgNHo. 



To prepare this substance f paranitraniline was suspended in water, 

 and converted by the addition of bromine into dibromparanitraniline. 

 Then fifty grams of this product were mixed in a flask with hydro- 

 bromic acid (boiling at 125°), and sodic nitrite added in excess. After 

 the last portion of the nitrite had been decomposed, a large excess of 

 hydrobromic acid was added, and the contents of the flask allowed to 

 stand over night. The diazo compound formed was then decomposed 

 by heating on the steam bath ; and the tribromnitrobenzol obtained was 

 reduced with tin and hydrochloric acid without any previous purification, 

 when most of the tribromaniline separated in the solid state, although 

 a small amount could be recovered from the hydrochloric acid solution. 

 It was purified by crystallization from alcohol or hot ligroin. 



Properties. — It crystallizes from alcohol and water in slender white 

 needles, rather short and pointed at both ends. Although it crystallizes 

 in needles like the ordinary tribromaniline, it differs from that in habit, 

 as we could not succeed in obtaining very long needles similar to those 

 which are so characteristic of the NHol, Br 2, Br 4, Br 6 isomere. It 

 melts between 118° and 119°, while the highest melting point given for 

 the isomeric form is that of Fittig and Buchner, 119°-120°. It is soluble 

 in ether, chloroform, benzol, acetone, or alcohol ; slightly soluble in cold, 

 soluble in hot ligroin ; essentially insoluble in water. Dilute alcohol or 

 hot ligroin is the best solvent for it. It forms salts more readily than 

 the NHo 1, Brg 2, 4, 6 tribromaniline, and a little less readily than the 

 NHo 1, Brg 2, 4, 5 tribromaniline. $ With bromine it gives pentabrom- 

 aniline. By the elimination of its amido group it is converted into the 

 vicinal tribrombenzol melting at 87°. 



& 



Chloride of Tribromaniline, NIIol, Bi-g 3, 4, 5. 



This salt could be made by boiling the tribromaniline with a large 

 excess of concentrated hydrochloric acid, but was prepared for analysis 

 by the more convenient method of dissolving the tribromaniline in benzol 



* Amer. Clicm. Jmirn., XVIII. 238. 



t Koenier, Gazz. Chim., 1874, pp. 347, 390. 



X Amer. Chem. Joiirn., XVIII. 247. 



