OP ARTS AND SCIENCES. 149 



C 6 H 5 OMHC 6 H 6 

 I 

 OCOH 



which Elbers * first obtained from phenylglyoxylic acid and phe- 

 nylhydrazine. Hence it is proved that the above two substances 

 are in reality derivatives of benzoylforrnic acid. 



III. On ^-Tolylisocyanide, CH 3 -C 6 H 4 -N=C=. 



Preparation of p-Tolyllsocyanide. — This substance was obtained 

 from j>-toluidine, etc., exactly as above in the case of the ortho 

 derivative, except that the isonitrile was not distilled over with 

 steam, which probably would have been an advantage. 22 grams 

 crude ^>-tolylisocyanide were obtained from 100 grams of ^?-tolui- 

 dine; it was distilled twice under reduced pressure. In the first 

 distillation, a large amount of residue remained; on the second 

 distillation, the isonitrile came over at 99° at 36 mm., and no resi- 

 due was left. It is a colorless oil, which on standing becomes 

 colored greenish yellow. 



0.1137 gram substance gave 0.3398 gram C0 2 and 0.0639 gram 



H 2 0. 

 0.2117 gram substance gave 22 c.c. moist nitrogen at 20° and 



752 mm. 



Theory for C 8 H 7 N. Found. 



C 82.05 81.50 



H 5.98 6.24 



N 11.97 11.77 



j9-tolylisocyanide has a smell which is markedly different from 

 that of the other two isonitriles obtained above; yet it is difficult 

 to describe in words the difference. The smell is at first pleasant 

 and aromatic, but also gradually excites nausea. 



Isocyan-p-tolylchl oriole, or p- Tolylimidocarbonylchloride, 

 CH 3 -C 6 H 4 N=C=C1 2 . 



The preparation of this substance is entirely analogous to that of 

 the corresponding ortho derivative. A colorless sharp-smelling oil 

 is obtained, which attacks the eyes, and boils at 225°-226° (un- 

 corr.). 



* Ann. Chem. (Liebig), CCXXVII. 341. 



