Xylyl bromides

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Xylyl bromides
Surname o -xylyl bromide m -xylyl bromide p -xylyl bromide
other names 2-methylbenzyl bromide 3-methylbenzyl bromide 4-methylbenzyl bromide
Structural formula O-xylyl bromide, svg M-xylyl bromide.svg P-xylyl bromide.svg
CAS number 89-92-9 620-13-3 104-81-4
Molecular formula C 8 H 9 Br
Molar mass 185.06 g mol −1
Physical state liquid firmly
Melting point 20 ° C - 38 ° C
boiling point 223 ° C 212-215 ° C 220 ° C
solubility poorly soluble in water ,
readily soluble in non-polar solvents such as ethanol or ether
GHS
labeling
05 - Corrosive 06 - Toxic or very toxic
danger
05 - Corrosive 06 - Toxic or very toxic
danger
05 - Corrosive 06 - Toxic or very toxic
danger
H and P phrases 330-314 330-314 330-314
no EUH phrases no EUH phrases no EUH phrases
260-303 + 361 + 353
305 + 351 + 338-320-405-501
260-303 + 361 + 353
305 + 351 + 338-320-405-501
260-303 + 361 + 353
305 + 351 + 338-320-405-501

The xylyl bromides , also known as methylbenzyl bromides , are bromine derivatives of xylene . They are obtained from the action of bromine on the xylenes , with an H atom in the side chain being replaced by a Br atom. The different arrangement of the substituents results in three constitutional isomers ( o -, m -, and p -Xylyl bromide) with the empirical formula C 8 H 9 Br.

properties

The xylyl bromides are insoluble in water, but readily soluble in ethanol and ether . O -Xylyl bromide has the greatest eye irritation ; it crystallizes in colorless prismatic crystals. The p -xylyl bromide, which has the highest symmetry, has the highest melting point.

history

In imperial Germany it was referred to as T-Stoff or lilac gas (in Great Britain as Elder-gas) and considered and also used as a chemical warfare agent. Xylyl bromide was used in the First World War, z. B. in January 1915 through Germany near Bolimow and Łódź . The effect was small due to the prevailing low outside temperatures, since not enough xylyl bromide could evaporate. During a mission on the Western Front in March 1915 near Nieuport (West Flanders), the "success" was greater due to higher temperatures.

Individual evidence

  1. a b c d e Entry on o-xylyl bromide in the GESTIS substance database of the IFA , accessed on November 20, 2015(JavaScript required) .
  2. a b Entry on m-xylyl bromide in the GESTIS substance database of the IFA , accessed on November 20, 2015(JavaScript required) .
  3. a b Entry on p-xylyl bromide in the GESTIS substance database of the IFA , accessed on November 20, 2015(JavaScript required) .