218 PROCEEDINGS OF THE AMERICAN ACADEMY 



A number of bromine determinations made in products from 

 •distillation with steam gave invariably results which were below the 

 theory. 



Properties. — It forms a pale yellow oil (the color is undoubtedly 

 due to a trace of some impurity), with an agi'eeable odor, somewhat 

 resembling that of parabrombenzylbromide, and an action on the 

 mucous membrane even more violent than that of the preceding com- 

 pounds ; its boiling-point seems to lie between 250° and 260°, but 

 could not be determined with accuracy because it is decomposed with 

 evolution of hydrobromic acid by boiling. A careful study of the 

 action of heat on this and the allied substances is reserved for a future 

 2)aper. It does not solidify even at — 15°, can be distilled with 

 steam, burns with the usual luminous green-bordered flame, and 

 does not mix with water, although it imparts its odor to it, but 

 mixes readily with absolute alcohol, ether, benzole, glacial acetic 

 acid, and carbonic disulphide. It does not seem to be attacked 

 by a mixture of potassic dichromate and dilute sulphuric acid, but 

 the alcohol derived from it is completely destroyed by this oxidizing 

 mixture. 



ParacMorbenzylhromide,G^Hj^ClCH„Br, was prepared from para- 

 chlortoluol ; melting-jwint, 6°. 5 ; boiling-point, lo8°-161'* ; made by the 

 modification of the method of Hiibner and Majert, already described in 

 connection with orthobromtoluol (see page 216); crude fuming hydro- 

 chloric acid took the place of the hydrobromic acid,and 40 gr. of paratolu- 

 idin were used for each operation ; the oil, after washing with potassic 

 hydrate, proved on rectification to be almost absolutely pure parachlorto- 

 luol, the yield being about 13 gr. It was converted into parachlorbenzyl- 

 bromide in the way already described ; the product of the reaction 

 deposited crystals on cooling, which were drained, and a fresh crop 

 obtained from the mother-liquor by heating it gently for a few minutes 

 in a watch-glass placed on a sand-bath, and then allowing it to stand 

 for some time. The crystals after pressing between filter-paper were 

 purified by crystallization from hot alcohol in corked flasks, as the sub- 

 stance is so volatile that work in open vessels would have been at- 

 tended with great loss ; upon cooling the solution with ice. a little oil 

 separated; and if the liquid was then stirred it immediately became filled 

 with beautiful white needles. On one occasion, the substance was dis- 

 tilled with steam in order to obtain it perfectly white, but this is not to 

 be recommended, as the water left in the distillation-flask deposited long 

 thin ribbons melting at 66°, and therefore evidently the jiarachlorbenzyl- 

 alcohol, while the supernatant liquid contained hydrobromic acid. This 



