276 TOLUENE. 



Bromine substitution-products. Parabromto- 

 luene, C 6 H 4 Br.CH 3 (colorless crystals; fusing point, 

 28.5; boiling point, 181), and Dibromtoluene (col- 

 orless needles; fusing point, 107-108; boiling point, 

 245) are produced by the action of bromine on toluene 

 without the aid of heat. Orthobromtoluene,C G TL*T$r.CIL 3 . 

 From diazoorthobromtoluene sulphate with absolute 

 alcohol. Liquid, boiling at 182-183. Metabromto- 

 luene C 6 H 4 Br.CH 3 , from diazometabromtoluene sul- 

 phate with absolute alcohol. Liquid, boiling at 182. 

 Yields, with bromine, a liquid, dibromtoluene, boiling 

 at 238-239, that does not congeal at 20. Benzyl 

 bromide, C 6 H 5 .CH 2 Br, is obtained by the action of bro- 

 mine on boiling toluene ; and by the decomposition of 

 benzyl alcohol by means of hydrobromic acid. Color- 

 less liquid ; gives off fumes in contact with the air and 

 excites to tears; boiling point, 198-199. Benzol bro- 

 mide, C 6 H 5 .CHBr 2 , is produced by the action of phos- 

 phorus pentabromide on oil of bitter almonds. A 

 liquid that cannot be distilled without suffering par- 

 tial decomposition. 



Paraiodotoluene, C 6 H 4 I.CH 3 (laminse; fusing 

 point, 35 ; boiling point, 211.5), and Orthoiodoto- 

 luene (a liquid, boiling at 201) are produced by the 

 action of hydriodic acid on the diazotoluene sulphates, 

 prepared from the corresponding toluidins. Benzyl 

 iodide, C 6 H 5 .CH 2 I (colorless crystals, fusing at 24, not 

 volatile without decomposition), is produced by the 

 action of hydriodic acid on benzyl chloride at the 

 ordinary temperature. 



Benzyl cyanide, C 6 H 5 .CH 2 .C, is obtained by 

 boiling benzyl chloride with alcohol and potassium 

 cyanide ; and by distilling potassium benzylsulphate, 

 with potassium cyanide. Colorless liquid, boiling at 

 229. 



Paranitrotoluene, C 6 H 4 (N0 2 ).CH 3 , and Orthoni- 



trotoluene are produced by treating toluene with 

 fuming nitric acid. The former forms almost color- 



