i8 Compounds of Hexamethylejietetramine 



properties of the dibromine derivative, (CH2)6N4Br2, described 

 by Legier and by Horton, were fully confirmed. Attempts at re- 

 crystallization were unsuccessful. 



loDiNE DERIVATIVES. Horton, in 1888, described di- and tetrai- 

 odine Compounds of hexamethylenetetramine. 



The tetraiodine Compound may be prepared by adding to 5 gm. 

 of hexamethylenetetramine in 100 cc. of water, 18. i gm. of iodine 

 in 300 cc. of 95 percent ethyl alcohol. The precipitate first formed 

 is dark grey, becomes lighter colored after further addition of 

 iodine, and finally red. After standing over night it is filtered 

 and washed three times witli 5-10 cc. of 95 percent ethyl alcohol. 

 After drying in a vacuum desiccator, 22.0 gm. (calc, 23.1 gm.) of 

 brownish red crystals are obtained. The nitrogcn determinations 

 (Kjeldahl) yielded the following results : 



0.1038 gm. of substance gave 0.00878 gm. of N, or 8.46 percent of N 



0.1008 gm. " " 0.00862 gm. " " 8.5s percent of N 



0.1038 gm. " " 0.00894 gm. " " 8.61 percent of N 



Mean: 8.54 percent of N; calc. for (CH2)6NJi, 8.65 percent of N. 



The best medium for recrystallization was found to be Chloro- 

 form, from whicli the substance was deposited in characteristic, 

 well formed, mahogany-red, monoclinic crystals. Nitrogen deter- 

 minations of the recrystallized material gave the following results : 



0.2003 gm. of substance gave 0.01695 gm- of N, or 8.46 percent of N 



0.2018 gm. ■ " " 0.01706 gm. " " 8.4s percent of N 



0.2050 gm. " " 0.01744 gm. " " 8.51 percent of N 



Mean : 8.47 percent of N. 



After Standing for nine months in diffused daylight, in a stop- 

 pered bottle, the crystals had become black but still retained their 

 monoclinic shapes. Nitrogen determinations gave a mean value (for 

 four analyses) of 8.44 percent. An iodine determination by the 

 Carius method, with recrystallized substance, gave 0.2869 gm. of 

 silver iodide from 0.1998 gm. of substance, or 77.6 percent of I ; calc. 

 for tetraiodine Compound, 78.4 percent. The iodine in the complex 

 may also be titrated directly with w/25 thiosulfate sol. after addi- 

 tion of 50 cc. of water and 3 cc. of glacial acetic acid. Starch sol. 

 is added near the end, and the lumps of tetraiodine Compound must 



