Chlorotoluenes

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Chlorotoluenes
Surname 2-chlorotoluene 3-chlorotoluene 4-chlorotoluene
other names 2-chlorotoluene,
o -chlorotoluene,
2-chloro-1-methylbenzene 		3-chlorotoluene,
m -chlorotoluene,
3-chloro-1-methylbenzene 		4-chlorotoluene,
p -chlorotoluene,
4-chloro-1-methylbenzene
Structural formula Structure of o-chlorotoluene Structure of m-chlorotoluene Structure of p-chlorotoluene
CAS number 95-49-8 108-41-8 106-43-4
25168-05-2 (mixture of isomers)
PubChem 7238 7931 7810
ECHA InfoCard 100.002.205 100.003.255  100.003.089
100.042.438 ( 100.137.417 ) (mixture of isomers)
Molecular formula C 7 H 7 Cl
Molar mass 126.59 g mol −1
Physical state liquid
Brief description colorless liquid
with an aromatic odor 		colorless liquid
Melting point −35 ° C −48 ° C 7.5 ° C
boiling point 159 ° C 162 ° C 162 ° C
density 1.08 g cm −3 (20 ° C) 1.08 g cm −3 (20 ° C) 1.07 g cm −3 (20 ° C)
Vapor pressure 3.82 hPa (20 ° C) 3.8 hPa (20 ° C) 3.6 hPa (20 ° C)
Solubility
in water 		50 mg l −1 (20 ° C) 106 g l −1 (25 ° C) 110 g l −1 (25 ° C)
Flash point 43 ° C 48 ° C 59 ° C
Ignition temperature > 550 ° C > 550 ° C 570 ° C
Explosion limits 1.3 to 8.3%
GHS
labeling 		from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary
02 - Highly / extremely flammable 07 - Warning 09 - Dangerous for the environment
Caution
H and P phrases 226-332-361d-410 226-332-411 226-317-332-411
no EUH phrases
273-210-280
304 + 340-310 		210-273 273-280
Tox data 3900 mg kg −1 ( LD 50 ,  rat ,  oral ) 2100 mg kg −1 ( LD 50 ,  rat ,  oral )

In chemistry, chlorotoluenes form a group of substances that is derived from both toluene and chlorobenzene . The structure consists of a benzene ring with attached methyl group  (–CH 3 ) and chlorine  (–Cl) as substituents . Their different arrangement results in three constitutional isomers with the empirical formula C 7 H 7 Cl. The isomer chlorinated on the methyl group is known as benzyl chloride .

properties

The chlorotoluenes are practically insoluble in water; however, they are with other organic solvents, such as. B. benzene, alcohol, ether, ethyl acetate and chloroform, freely mixable. The boiling points of the three isomers are close to one another, while their melting points differ significantly. The 4-chlorotoluene, which has the highest symmetry, has the highest melting point.

Vapor-liquid equilibria
Surname 2-chlorotoluene 3-chlorotoluene 4-chlorotoluene
Vapor pressure function after Antoine Parameters according to log 10 (P) = A− (B / (T + C)) (P in bar, T in K)
A. 4,48741 4.48148 4.47458
B. 1768.105 1807.576 1795.293
C. −38.389 −32.105 −34.380
Temperature range 278.4K - 432.5K 277.9K - 435.5K 278.7K - 435.5K
source

presentation

The chlorotoluenes can be prepared from the toluidines by means of the Sandmeyer reaction . A mixture of 2- and 4-chlorotoluene is obtained by chlorinating toluene with chlorine and iron , iron (III) chloride being formed as a Lewis acid .

use

Chlorotoluenes are used as solvents and as an intermediate in the manufacture of dyes , pesticides and drugs.

See also

Chlorotoluenes with more than one chlorine atom are called polychlorinated toluenes.

safety instructions

Chlorotoluenes can decompose plastics and slightly corrode metals. The thermal decomposition of chlorotoluenes forms toxic and corrosive hydrogen chloride .

Individual evidence

  1. ↑ Entry on chlorotoluene, isomers in the GESTIS substance database of the IFA , accessed on December 26, 2019(JavaScript required) .
  2. ↑ a b c d e f g h i j k l Entry on 2-chlorotoluene in the GESTIS substance database of the IFA , accessed on December 26, 2019(JavaScript required) .
  3. ↑ a b c d e f g h i j k Entry on 3-chlorotoluene in the GESTIS substance database of the IFA , accessed on December 26, 2019(JavaScript required) .
  4. ↑ a b c d e f g h i j k l Entry on 4-chlorotoluene in the GESTIS substance database of the IFA , accessed on December 26, 2019(JavaScript required) .
  5. ↑ Entry on Chlorotoluene in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 11, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
  6. ^ Stull, DR: Vapor Pressure of Pure Substances. Organic and Inorganic Compounds in Ind. Eng. Chem. 39 (1947) 517-540, doi : 10.1021 / ie50448a022 .
  7. ^ Association of authors: Organikum , 19th edition, Johann Ambrosius Barth, Leipzig · Berlin · Heidelberg 1993, ISBN 3-335-00343-8 , p. 566.