MOLECULAR CONSTITUTION OF THE VOLATILE ORGANIC BASES. 
113 
Action of Bromide and Iodide of Methyl upon Aniline. 
Methylaniline {Methylophenylamine ) . 
Tbe deportment of aniline with bromide of methyl resembles its behaviour with 
the ethyl-compound. The mixture rapidly solidifies into a crystalline mass of 
hydrobrornate of methylaniline. Bromide of methyl being’ extremely volatile, I have 
used also the iodide, which boils at a more convenient temperature. The action of 
the latter compound upon aniline is very remarkable, the evolution of heat, on mixing 
the two substances, being so great, that the liquid enters into violent ebullition, so 
that unless the substances be mixed gradually, the crystalline hydriodate, which is 
formed immediately, is actually thrown out of the vessel. 
Methylaniline, when separated from the hydrobrornate or hydriodate, appears as a 
transparent oil of a’peculiar odour, somewhat different from that of aniline, and boiling 
at 192° ; it has retained the properties of aniline in a higher degree than the ethylated 
compound. This substance yields still the blue coloration with hypochlorite of 
lime, although in a less degree than aniline. Its salts are less soluble than those of 
ethylaniline ; they are at once formed in the crystalline state on addition of the re- 
spective acids ; the oxalate crystallizes very easily, but is rapidly decomposed with 
reproduction of aniline, and probably with formation of oxalate of methyl^. 
The composition of methylaniline is represented by the expression 
n u TV— r ^ "^ N— 
’-^14 ^9 H — 
H 
C 
H 3 N. 
ic", H^J 
I have established this formula by the analysis of the platinum-salt. This is pre- 
cipitated as a transparent oil, which rapidly changes into pale-yellow crystalline tufts, 
resembling the corresponding aniline-salt, but liable to rapid decomposition. The 
washing must be quickly done, for the salt is extremely soluble in water, and must 
be immediately followed by desiccation. Even when very carefully prepared, it has 
become dark by the time it is ready for combustion. It turns instantaneously black 
if an alcoholic solution of the hydrochlorate be employed for its preparation. 
Analysis I. refers to a salt obtained with the base prepared by means of the bro- 
mide ; for analysis II. the base had been formed by the iodide. The specimen ana- 
lysed under III. again had been obtained with the bromide, but it was in an advanced 
state of decomposition, and had in consequence become perfectly black. 
I. 0*1018 grm. of platinum-salt gave 0*0319 grro. of platinum. 
II. 0*2467 grm. of platinum-salt gave 0*0784 grm. of platinum. 
III. 0*2065 grm. of platinum-salt gave 0*0660 grm. of platinum. 
* The aniline thus reproduced was identified by the analysis of the platinum-compound. 
0’7910 grm. of platinum-salt gave 0'2615 grm. of platinum. 
Experimental. Theoretical percentage of platinum in aniline-platinum-salt. 
33-05 32-98 
MDCCCL. 
Q 
