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1,2,4-Trichlorobenzene

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CAS:120-82-1
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  • 2023-12-26
  • CAS:120-82-1
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1,2,4-Trichlorobenzene Chemical Properties
Melting point 16 °C(lit.)
Boiling point 214 °C(lit.)
density 1.454 g/mL at 25 °C(lit.)
vapor density >6 (vs air)
vapor pressure 1 mm Hg ( 40 °C)
refractive index n20/D 1.571(lit.)
Fp >230 °F
storage temp. 2-8°C
solubility water: insoluble
form Liquid
color Clear
OdorCharacteristic aromatic odor
explosive limit6.6%, 150°F
Water Solubility INSOLUBLE
λmaxλ: 308 nm Amax: 1.00
λ: 310 nm Amax: 0.50
λ: 350 nm Amax: 0.05
λ: 375-400 nm Amax: 0.01
Merck 14,9631
BRN 956819
Henry's Law Constant0.997 at 20.0 °C (wetted-wall column, ten Hulscher et al., 1992) 1.24, 2.27, 2.58, 3.06, and 3.90 at 2.0, 6.0, 10.0, 18.0, and 25.0 °C, respectively (EPICS-SPME, Dewulf et al., 1999)
Exposure limitsNIOSH REL: TWA ceiling 5 ppm (40 mg/m3); ACGIH TLV: ceiling 5 ppm (adopted).
Dielectric constant2.2400000000000002
Stability:Stable. Incompatible with strong oxidizing agents. Combustible.
LogP4.28
CAS DataBase Reference120-82-1(CAS DataBase Reference)
NIST Chemistry ReferenceBenzene, 1,2,4-trichloro-(120-82-1)
EPA Substance Registry System1,2,4-Trichlorobenzene (120-82-1)
Safety Information
Hazard Codes Xn,N,Xi,T,F
Risk Statements 22-38-50/53-52/53-39/23/24/25-23/24/25-11-51/53
Safety Statements 23-37/39-60-61-45-36/37-16-7
RIDADR UN 2321 6.1/PG 3
WGK Germany 3
RTECS DC2100000
Autoignition Temperature571 °C
Hazard Note Irritant
TSCA Yes
HazardClass 6.1
PackingGroup III
HS Code 29036990
Hazardous Substances Data120-82-1(Hazardous Substances Data)
ToxicityLD50 orally in Rabbit: 550 mg/kg LD50 dermal Rat 6139 mg/kg
MSDS Information
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1,2,4-Trichlorobenzene Usage And Synthesis
DescriptionTrichlorobenzenes (TCBs) are synthetic chemicals that occur in three different isomeric forms. The three chlorinated cyclic aromatic isomers are 1,2,3-trichlorobenzene (1,2,3-TCB), 1,2,4-trichlorobenzene (1,2,4-TCB), and 1,3,5-trichlorobenzene (1,3,5-TCB). 1,2,4-TCB is one of the 188 chemicals designated as a hazardous air pollutant under the Clean Air Act.
Chemical Properties1,2,4-Trichlorobenzene is a low-melting solid or liquid with a pleasant, aromatic odor. The Odor Threshold is 1.4 ppm.
Physical propertiesColorless liquid with an odor similar to o-dichlorobenzene. Odor threshold concentration is 1.4 (quoted, Amoore and Hautala, 1983). Miscible with most organic solvents and oils; insoluble in water. Combustible.
Uses1,2,4-Trichlorobenzene is used as a dielectric and heat transfer fluid in transformers. It acts as an intermediate, degreaser, wood preservative and solvent for dye. It is a high-temperature solvent used in gel permeation chromatography, especially for polyethylene and polypropylene. Further, it is used as a lubricant and as a synthetic transformer oil.
DefinitionChEBI: 1,2,4-trichlorobenzene is a trichlorobenzene with chloro substituents at positions 1, 2 and 4. It is a solvent in various organic chemical reactions.
ApplicationTrichlorobenzenes are primarily used as solvents in chemical manufacturing industries. 1,2,4-Trichlorobenzene is economically the most important isomer. It is used as a solvent in chemical reactions to dissolve oils, waxes, and resins. Furthermore, it is also used as a dye carrier. 1,2,4-Trichlorobenzene is a highly chlorinated aromatic solvent. It may be used as a solvent to prepare:
dimethylketene β-lactone dimer from tetramethyl-1,3-cyclobutanedione
salicyl-o-toluide by the reaction of phenyl salicylate and o-toluidine
Synthesis Reference(s)Journal of the American Chemical Society, 74, p. 3890, 1952 DOI: 10.1021/ja01135a052
General DescriptionColorless liquid or white solid with a sharp chlorobenzene odor. Melting point 16.95°C (62.5°F) .
Reactivity Profile1,2,4-Trichlorobenzene can react vigorously with oxidizing materials . Yields hydrogen chloride and phosgene when heated to decomposition [USCG, 1999].
Health HazardExposures to high concentrations via inhalation are potentially hazardous to the lungs, kidneys and liver. Prolonged or repeated exposures or short exposure to high concentrations via inhalation are potentially hazardous to the lungs, kidneys and liver. Prolonged or repeated exposure to the eyes is likely to result in moderate pain and transient irritation. Prolonged or repeated contact with the skin may result in moderate irritation and possible systemic effects. Ingestion: May cause kidney and liver damage.
Safety ProfilePoison by ingestion. Moderately toxic by intraperitoneal route. An experimental teratogen. Experimental reproductive effects. Mutation data reported. A slan irritant. Combustible when exposed to heat or flame. Can react vigorously with oxidizing materials. To fight fire, use water, foam, CO2, dry chemical. When heated to decomposition it emits toxic fumes of Cl-. See also CHLORINATED HYDROCARBONS, AROMATIC.
Potential Exposure1,2,4-Trichlorobenzene is used as a dye carrier, herbicide intermediate; a heat transfer medium; a dielectric fluid in transformers; a degreaser; a lubricant; as an industrial chemical; solvent, emulsifier, and as a potential insecticide against termites. The other trichlorobenzene isomers are not used in any quantity.
Environmental fateBiological. Under aerobic conditions, biodegradation products may include 1,2-dichlorobenzene, 1,3-dichlorobenzene, 1,4-dichlorobenzene, and carbon dioxide (Kobayashi and Rittman, 1982). A mixed culture of soil bacteria or a Pseudomonas sp. transformed 1,2,4-trichlorobenzene to 2,4,5- and 2,4,6-trichlorophenol (Ballschiter and Scholz, 1980). When 1,2,4- trichlorobenzene was statically incubated in the dark at 25 °C with yeast extract and settled domestic wastewater inoculum, significant biodegradation occurred, with gradual acclimation followed by a deadaptive process in subsequent subcultures. At a concentration of 5 mg/L, 54, 70, 59, and 24% losses were observed after 7, 14, 21, and 28-d incubation periods, respectively. At a concentration of 10 mg/L, only 43, 54, 14, and 0% were observed after 7, 14, 21, and 28-d incubation periods, respectively (Tabak et al., 1981). In activated sludge, <0.1% mineralized to carbon dioxide after 5 d (Freitag et al., 1985).
In an enrichment culture derived from a contaminated site in Bayou d’Inde, LA, 1,2,4- trichlorobenzene underwent reductive dechlorination to 1,3- and 1,4-dichlorobenzene at relative molar yields of 4 and 96%, respectively. The maximum dechlorination rate, based on the recommended Michaelis-Menten model, was 4.6 nM/d (Pavlostathis and Prytula, 2000).
Surface Water. Estimated half-lives of 1,2,4-trichlorobenzene (0.5 μg/L) from an experimental marine mesocosm during the spring (8–16 °C), summer (20–22 °C), and winter (3–7 °C) were 22, 11, and 12 d, respectively (Wakeham et al., 1983).
Photolytic. A carbon dioxide yield of 9.8% was achieved when 1,2,4-trichlorobenzene adsorbed on silica gel was irradiated with light (λ >290 nm) for 17 h (Freitag et al., 1985).
Chemical/Physical. The hydrolysis half-life was estimated to be >900 yr (Ellington et al., 1988). At 70.0 °C and pH values of 3.10, 7.11, and 9.77, the hydrolysis half-lives were calculated to be 18.4, 6.6, and 5.9 d, respectively (Ellington et al., 1986).
At influent concentrations of 1.0, 0.1, 0.01, and 0.001 mg/L, the GAC adsorption capacities were 157, 77.6, 38.4, and 19.0 mg/g, respectively (Dobbs and Cohen, 1980).
ShippingUN2321 Trichlorobenzenes, liquid, Hazard Class: 6.1; Labels: 6.1-Poisonous materials.
Purification MethodsSeparate it from a mixture of isomers by washing with fuming H2SO4, then water, drying with CaSO4 and slowly fractionally distilling. [Jensen et al. J Am Chem Soc 81 3303 1959, Beilstein 5 IV 664.]
Toxicity evaluationThe liver is themain target of trichlorobenzenes irrespective of the route of exposure. The mechanisms of liver toxicity induced by these chemicals have not been illustrated. It might involve intermediate arene oxides formed during initial transformation to trichlorophenols. In addition, exposure to 1,2,4-TCB induced porphyria in rats by inducing daminolevulinic acid (ALA) synthetase, a rate-limiting enzyme in the biosynthesis of heme, and also heme oxygenase, a ratelimiting enzyme in the degradation of heme synthetase, and therefore increasing heme production.
IncompatibilitiesReacts violently with oxidants, acids, acid fumes; steam.
Waste DisposalIncineration, preferably after mixing with another combustible fuel. Care must be exercised to assure complete combustion to prevent the formation of phosgene. An acid scrubber is necessary to remove the halo acids produced.
Tag:1,2,4-Trichlorobenzene(120-82-1) Related Product Information
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