Xylyl bromides
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 | |||||||||
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 |
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GHS labeling |
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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
- ↑ 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) .
- ↑ a b Entry on m-xylyl bromide in the GESTIS substance database of the IFA , accessed on November 20, 2015(JavaScript required) .
- ↑ a b Entry on p-xylyl bromide in the GESTIS substance database of the IFA , accessed on November 20, 2015(JavaScript required) .