1869.] 



Action of Bromine upon Ethylbenzol. 



127 



any difference in the hind of substitution effected by the halogen in the 

 presence or absence of iodine. 



Beilstein also has recently shown tha; the action upon toluol varies ma- 

 terially with the conditions under which the experiment is performed. 

 When a stream of chlorine is passed through carefully cooled toluol, chlor- 

 toluol, C 6 H 4 C1{CH 3 , only is formed; this body is characterized by a 

 high degree of stability, resisting completely the action of potassium cyan- 

 ide, potassium sulphide, and silver-salts. On the other hand, if the toluol is 

 previously heated, or if, through the energy of the action, its temperature be 

 allowed to rise, the relative position of the substituting chlorine atom is essen- 

 tially changed, and under these circumstances chlorbenzyl, C 6 H 5 {CH 2 C1, 

 is found to be the main product of the reaction : this substance differs 

 from the isomeric chlortoluol by the facility with which it yields up its 

 chlorine by double decomposition. But if a small quantity of iodine be 

 added to the hydrocarbon before treatment with chlorine, chlortoluol only 

 is produced, no matter whether the chlorine acts upon boiling or upon cold 

 toluol. 



To the bromide obtained by the action of bromine free from iodine on 

 cold ethylbenzol I assign the formula C 6 H.{C 2 H 4 Br, on the assumption 

 that it is identical with that prepared by Berthelot. From the ease with 

 which the compound yielded its bromine to alcoholic ammonia, I was in- 

 duced to attempt the preparation of the corresponding amines. A quantity 

 of the bromide was sealed up in wide glass tubes with about four times its 

 volume of absolute alcohol saturated with ammoniacal gas, and the mix- 

 ture exposed to a temperature of 100° C. for about three hours. When 

 all action had apparently ended, the tubes were reopened and the liquid 

 portion drained from the bulky precipitate of ammonium bromide. On 

 treating the liquid with water, a light mobile agreeablys melling liquid 

 separated out ; this was washed, dried by means of calcium chloride, and 

 distilled; by far the greater portion boiled at 185°-187° C. This liquid 

 was found to be free from nitrogen and bromine, and yielded on analysis 

 the following numbers : — 



I. 0*1552 grm. substance gave 0*4540 grm. carbonic anhydride and 

 0*1333 grm. water. 



II. 0*2011 grm. substance gave 0*5896 grm. carbonic anhydride and 

 0*1078 grm. water. 



Calculated. Found. 



7. ii? 



C 10 120 80-00 79*79 79*98 



H 14 14 9*36 9*53 9*44 



O 16 



The constitution of this compound may be expressed by the formula 



