1,2,4-Trichlorobenzene

1,2,4-Trichlorobenzene is an organochlorine compound, one of three isomers of trichlorobenzene. It is a derivative of benzene with three chloride substituents. It is a colorless liquid used as a solvent for a variety of compounds and materials.

1,2,4-Trichlorobenzene
Names
Preferred IUPAC name
1,2,4-Trichlorobenzene
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.004.026 Edit this at Wikidata
UNII
  • InChI=1/C6H3Cl3/c7-4-1-2-5(8)6(9)3-4/h1-3H<
  • Clc1ccc(Cl)c(Cl)c1
Properties
C6H3Cl3
Molar mass 181.44 g·mol−1
Appearance Colorless liquid
Odor aromatic[1]
Density 1.46 g cm−3
Melting point 16.9 °C (62.4 °F; 290.0 K)
Boiling point 213.5 °C (416.3 °F; 486.6 K)[2]
0.003% (20 °C)[1]
Vapor pressure 1 mmHg (20 °C)[1]
Related compounds
Related compounds
1,2,3-Trichlorobenzene
1,3,5-Trichlorobenzene
Hazards
Flash point 110 °C (230 °F; 383 K)
Explosive limits 2.5%-6.6% (150°C)[1]
NIOSH (US health exposure limits):
PEL (Permissible)
none[1]
REL (Recommended)
C 5 ppm (40 mg/m3)[1]
IDLH (Immediate danger)
N.D.[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Production and uses

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Depending on the conditions and additives (e.g., sulfur), it can be the main product from the chlorination of benzene. It is virtually the exclusive product from the chlorination of 1,4-dichlorobenzene. It is also the main product from the dehydrochlorination of hexachlorocyclohexane.[3]

It is useful as a high-temperature solvent, e.g. for GPC of polyolefines such as PE or PP which are otherwise insoluble.

Aside from its use as a solvent, this compound is a useful precursor to dye and pesticides.

Safety

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The LD50 (oral, rats) is 756 mg/kg. Animal studies have shown that 1,2,4-trichlorobenzene affects the liver and kidney, and is possibly a teratogen.[4] There is no regulated occupational exposure limit for chemical exposure, but the National Institute for Occupational Safety and Health recommends no greater exposure than 5 ppm, over an 8-hour workday.

See also

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  • Chlorobenzenes—different numbers of chlorine substituents and isomeric forms

References

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  1. ^ a b c d e f g NIOSH Pocket Guide to Chemical Hazards. "#0627". National Institute for Occupational Safety and Health (NIOSH).
  2. ^ Jaw, Ching-Guang; Chen, I-Ming; Yen, Jui-Hung; Wang, Yei-Shung (December 1999). "Partial solubility parameters of chlorobenzene and chlorophenol compounds at equilibrium distribution in two immiscible phases". Chemosphere. 39 (15): 2607–2620. doi:10.1016/s0045-6535(99)00173-3. ISSN 0045-6535.
  3. ^ Beck, U.; Löser, E. "Chlorinated Benzenes and other Nucleus-Chlorinated Aromatic Hydrocarbons". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.o06_o03. ISBN 978-3527306732.
  4. ^ CDC - NIOSH Pocket Guide to Chemical Hazards