Chlorotoluenes
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 |
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Structural formula | ||||||
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
|
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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 | ||||
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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.
- Dichlorotoluenes , C 7 H 6 Cl 2
- Trichlorotoluenes , C 7 H 5 Cl 3
- Tetrachlorotoluenes , C 7 H 4 Cl 4
- Pentachlorotoluene , C 7 H 3 Cl 5
safety instructions
Chlorotoluenes can decompose plastics and slightly corrode metals. The thermal decomposition of chlorotoluenes forms toxic and corrosive hydrogen chloride .
Individual evidence
- ↑ Entry on chlorotoluene, isomers in the GESTIS substance database of the IFA , accessed on December 26, 2019(JavaScript required) .
- ↑ 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) .
- ↑ 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) .
- ↑ 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) .
- ↑ 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 .
- ^ Stull, DR: Vapor Pressure of Pure Substances. Organic and Inorganic Compounds in Ind. Eng. Chem. 39 (1947) 517-540, doi : 10.1021 / ie50448a022 .
- ^ Association of authors: Organikum , 19th edition, Johann Ambrosius Barth, Leipzig · Berlin · Heidelberg 1993, ISBN 3-335-00343-8 , p. 566.