336 PROCEEDINGS OP THE AMERICAN ACADEMY. 



Symmetrical Triiodbenzol, CeHalg. 



This substance was prepared as follows : Ten grams of the bufF- 

 colored triiodaniline, made as described in the previous section, were 

 boiled with 125 c.c. of benzol and 25 c.c. of alcohol, and disregarding 

 the undissolved portion, 5 c.c. of commercial sulphuric acid were added, 

 and then 5 grams of finely powdered sodic nitrite were sifted into the 

 liquid as quickly as possible. As soon as the evolution of nitrogen had 

 slackened sufficiently, the liquid was boiled for some time on the steam 

 bath, until a large part of the solvents had passed off ; during this boil- 

 ing a bright yellow solid, which formed on the particles of sodic nitrite 

 as they entered the liquid, changed its color to a light grayish brown. 

 After the solution had been boiled, it was allowed to stand over night, 

 and then the deposit was filtered out and washed, first with alcohol and 

 afterwards with hot water, to remove the inorganic salts. The amount 

 of this crude product rarely fell below 50 per cent of the theoretical yield. 



The product, obtained as described above, was next sublimed from a 

 large watch-slass heated on the sand bath, and covered with a funnel 

 which stood on a piece of filter paper above the substance. If this sub- 

 limation was carried on slowly enough, as much as 80 per cent of white 

 glistening crystals was obtained, but if it was urged too fast, the impuri- 

 ties also sublimed, and the crystals were yellow, or even in extreme 

 cases light brown and sticky. When proper care was used, white 

 crystals were obtained by this sublimation, even from very impure 

 products, such as those recovered by evaporating the liquid portion of the 

 product of the diazo reaction. The white sublimed crystals were not, 

 however, pure, and to remove from them a persistent impurity we found 

 repeated recrystallizations from alcohol were necessary, which finally 

 raised the melting point to 181°, where it remained constant. The sub- 

 stance was then dried at 100°, and analyzed with the following results : — 



I. 0.1187 gram of the substance gave by the method of Carius 0.1838 



gram of argentic iodide. 

 II. 0.1453 gram gave 0.2249 gram of argentic iodide. 



Calculated for Found. 



C6H3I3. I- II- 



Iodine 83.54 83.66 83.60 



Properties of 1.3.5 Triiodbenzol — This substance crystallizes from 

 alcohol at first in radiating groups composed of a few slender prisms, 

 which develop later into long white prisms frequently tapering, but 



