140 PROCEEDINGS OF THE AMERICAN ACADEMY. 



The tricblorbrombenzol Cl3l,3,5,Br2 melts at 65°, that is, at nearly 

 the same temperature as the symmetrical trichlorbenzol 63°. 4 (Korner), 

 and what is strange, higher than the corresponding trichloriodbenzol. 

 With sodic ethylate it lost bromine, but the reaction was not specially 

 studied. When treated with fuming nitric acid it gave a trichlorbrom- 

 dinitrobenzol melting at 175°, which was a decidedly reactive substance. 

 Aniline replaced the three atoms of chlorine, giving the trianilidobrom- 

 dinitrobenzol CG(C6rT5NH)3Br(NOo)2, melting at 175° to 176°, discovered 

 by W. D. Bancroft and one of us.* 



Sodic ethylate also acts upon it, probably giving a number of products, 

 to judge from analogy and the fact that both sodic bromide and sodic 

 nitrite were detected among them, but we have only succeeded in iden- 

 tifying one of these with certainty ; this is a bromdinitroresorcine diethyl- 

 ether melting at 81° to 82°, and probably having the following constitution, 

 (OC2ll5)2l?3,Br2(N02)24,6, although it may be that one of the ethoxy 

 groups stands at 5 instead of 3. It must have been formed by the re- 

 placement of two atoms of chlorine by two ethoxy groups, and the third 

 by hydrogen. As in most of the replacements of a halogen by hydrogen 

 it has been found that it stood between two uitro groups, we think there 

 can be little doubt that the first constitution assigned to this body is the 

 correct one. Its formation is interesting, as it is the first case we have 

 found iu which chlorine has been replaced by hydrogen under these 

 conditions. In all the otlier cases studied the clilorine has remained 

 unaltered, or has entered into some sim[)le reaction : thus picrylchloride 

 gave picryl ether,t picrylmalcftiic ester.J or picrylacetacetic ester, § 

 according to the reagent used ; chloranil gave dichlorquinonedimalonic 

 ester, || or, so far as the replacement alone was concerned, dichlordi- 

 ethoxyquinone ; If and trichlordinitrobenzol gave d;chlordinitrophenyl- 

 malonic ester,** or chlordinitroresorcine diethylether, and diuitrophloro- 

 glucine triethjdether.ft These last cases are especially striking, since the 

 corresponding tribromdinitrobenzol showed a replacement of bromine by 

 hydrogen, when treated with sodium malonic ester or sodic ethylate. 



* These Proceedings, XXIV. 293. 

 t Jackson and Boos, These Proceedings, XXIII. 176. 

 t Jackson and Soch, Ibid., XXX. 401. 

 § Dittrich, Ber. d. chem. Ges., XXIII. 2720. 

 II Stieglitz, Am. Chem. Journ., XIII. 38. 



IT Kelirmann, J. prakt. Chem., [2], XL. .367 ; Jackson and Grindley, These Pro- 

 ceedings, XXX. 430. 



** Jackson and Lamar, Am. Chem. Journ., XVIII. 775. 

 tt The same, Ibid., p. 668. 



