JACKSON AND GAZZOLO. NITRO COMPOUNDS. 275 



Action of Bromine on the Addition Product of Trinitrobenzol and Sodic 



Malonic Ester. 



The addition product C 6 H 3 (N0 2 ) 3 [CHNa(COOC 2 H 5 ) 2 ] 3 was added in 

 small successive portions to a chloroform solution of bromine cooled by 

 immersing the vessel in ice. The color of the solid changed instantly 

 from maroon to white. After the mixture had stood over night, the solid 

 was filtered out, and the filtrate allowed to evaporate spontaneously, when 

 it left a thick brownish red oil, which after standing two days deposited 

 crystals identified as trinitrobenzol by their melting-point, 121°, the form 

 of the crystals, and the formation of the characteristic red color with 

 sodic alcoholates. The portion insoluble in chloroform, after thorough 

 washing with chloroform and boiling benzol, proved to be sodic bromide. 

 This experiment does not absolutely disprove the formation of some 

 bromtrinitrobenzol, since a small amount of it might have remained dis- 

 solved in the oil from which the trinitrobenzol was deposited, but it 

 shows that trinitrobenzol is one of the principal products of the reaction ; 

 and as this separated from the oil in a nearly pure state, it is very prob- 

 able at least that no bromtrinitrobenzol was formed. 



Action of Sodic Acetacetic Ester on Trinitrobenzol. 



The product was prepared in the same way as the corresponding addi- 

 tion compound of trinitrobenzol and sodic malonic ester. In this case 

 the precipitate had a deeper red color than that produced with sodic 

 malonic ester, and the reaction ran less neatly. Analyses of three 

 different preparations dried in vacuo gave the following results : — 



I. 0.18G5 gram of the substance gave 0.0623 gram of sodic sulphate. 



II. 0.2017 gram of the substance gave 0.0G58 gram of sodic sulphate. 



III. 0.2104 gram of the substance gave 0.0680 gram of sodic sulphate. 



Calculated for Found. 



C c H 3 (N0 2 ) s [CH 3 C0CUNaC00C 2 II 5 ]3, I. II. III. 



Sodium 10.32 10.82 10.56 10.47 



The addition product of trinitrobenzol and sodic acetacetic ester is a 

 rich brownish red amorphous powder darker than the corresponding 

 product from trinitrobenzol and sodic malonic ester. It is fairly stable, 

 if kept dry. In its other properties it is exactly similar to the colored 

 substances already described in this paper. 



