182 PEOCEEDINGS OP THE AMERICAN ACADEMY 



in ether ; slightly soluble in glacial acetic acid or carbonic disulphide ; 

 very slightly soluble in hgroiue. The best solvent for it is a mixture 

 of alcohol and benzol. Neither strong sulphuric nor hydrochloric acid 

 seemed to have any action on it, hot or cold ; but strong nitric acid 

 dissolved it after a few minutes' heating, and gave on dilution a new 

 substance melting above 200°, probably a nitro compound. Sodic 

 hydrate in solution has no perceptible action on the substance. 



The removal of the bromine from the bromdinitroresorcine diphenyl- 

 ether interested us especially, as the somewhat more acid nature of the 

 phenol radical (C^H^O) would we thought exercise a marked influ- 

 ence on it ; unfortunately, however, the product has proved completely 

 unmanageable, so that we can give only a very imperfect account of 

 this action. We tried first hot sodic ethylate, but found that the sub- 

 stance was much more susceptible to its action than the corresponding 

 ethyl or methyl compounds, showing signs of decomposition by turn- 

 ing dark when the mixture was heated for ten minutes ; and although 

 a less colored solution was obtained when we heated for only three or 

 four minutes on the steam bath, the residue left after spontaneous 

 evaporation of the alcohol was a dark -colored oily liquid which showed 

 no signs of solidification, but gradually changed into a black tar after 

 standing some months, and could not be brought into a state fit for 

 analysis by any method we have been able to devise. The aqueous 

 wash water from this substance contained sodic bromide, so that there 

 is no question that the bromine has been removed, but we are unable 

 to determine whether it has been replaced by hydrogen or ethoxyl. 



We thought it possible that the bromine might be removed from 

 bromdinitroresorcine diphenylether by phenol, tribromphenol being 

 formed ; but after heating the substances together on the steam bath 

 for two days, essentially all the bromdinitroresorcine diphenylether 

 was recovered unaltered. A mixture of sodium malonic ester with 

 an excess of malonic ester seemed to have more effect, as the liquid 

 turned first pale yellow and then red. It was allowed to stand in the 

 cold for several weeks, when it was found that a small amount of 

 sodic bromide had been formed ; but the action was a very limited one, 

 as almost all of the bromdinitroresorcine diphenylether was recovered 

 unaltered, and the new compound was present in such small quantity 

 that we did not succeed in isolating it. 



Experiments with Trihromtrinitrobenzol. 



After we had found that the bromine in bromdinitroresorcine 

 diethylether could be replaced with hydrogen by the action of hot 



