CONTRIBUTIONS FROM THE CHEMICAL LABORATORY OF 



HARVARD COLLEGE. 



ON THE 3, 4, 5 TRIBROMANILINE AND SOME DERIVA- 

 TIVES OF UNSYMMETRICAL TRIBROMBENZOL. 



By C. Loring Jackson and F. B. Gallivan. 



Presented May 12, 1897. 



In the course of an attempt to prepare the vicinal tetrabrombenzol, 

 which unfortunately did not lead to the desired result, we had occasion 

 to make the 3, 4, 5 tribromaniline, when to our surprise our product 

 melted at 118° to 119°, whereas Koerner, who discovered the substance, 

 says of it, " non foiidente a 130°, e che, a quanto pare, si scompone 

 per un piii forte riscaldamento." * As the statement quoted from Koerner 

 contained all that was known of the properties of the substance, except 

 that he says also that it forms salts, we have made a more careful study 

 of this tribromaniline in order to characterize it. Our melting point not 

 only differed from Koerner's, but also was essentially identical with that 

 of the ordinary tribromaniline NHol, Brg 2, 4, 6, — which melts at 118° 

 according to Koerner, at 119°-120° according to Fittig and Buchner. 

 It was necessary, therefore, in the first place to prove that our sub- 

 stance was the tribromaniline NHgl, Brg 3, 4, 5, even although from our 

 knowledge of the positions usually taken by bromine atoms on the benzol 

 ring it seemed hardly possible that a body formed by the action of 

 bromine on paranitraniline could have a different constitution. To make 

 the proof absolute we eliminated the amido group from our tribromaniline, 

 when we found that the vicinal tribrombenzol melting at 87° and crystal- 

 lizing in tables was formed with remarkable ease. It follows, therefore, 

 that Koerner's statement that the tribromaniline (NHol, Br 3, Br 4, Br 5) 

 does not melt even at 130° is incorrect, and that it melts at 118°-119°. 

 We have added to the description of the compounds of this tribromani- 

 line which follows an account of some other substances obtained in our 



* Gazz. Chim., 1874, p. 409. 



