| Identification | More | [Name]
1,2,4-Trichlorobenzene | [CAS]
120-82-1 | [Synonyms]
TRICHLOROBENZENE
UNSYM-TRICHLOROBENZENE
1,2,4-trichloro-benzen
1,2,4-trichlorobenzene(tcb)
1,2,4-Trichlorobenzol
1,2,5-Trichlorobenzene
1,3,4-Trichlorobenzene
ai3-07775
as-trichlorobenzene
Benzene,1,2,4-trichloro-
Hipochem GM
Hostetex l-pec
hostetexl-pec
Trojchlorobenzen
trojchlorobenzen(polish)
Trichlorobenzene, 1,2,4-? Trichlorobenzol
TRICHLOROBENZENE124-,,
TRICHLOROBENZEN MIXTURE
1,2,4-TRICHLOROBENZENE SINGLE COMPONENT STANDARD FOR EPA
1,2,4-TRICHLOROBENZENE PESTANAL | [EINECS(EC#)]
204-428-0 | [Molecular Formula]
C6H3Cl3 | [MDL Number]
MFCD00000547 | [Molecular Weight]
181.45 | [MOL File]
120-82-1.mol |
| Chemical Properties | Back Directory | [Appearance]
Colorless, stable liquid; odor similar
to that of o-dichlorobenzene. Miscible with
most organic solvents and oils; insoluble in water.
Combustible. | [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. ]
0-6°C | [solubility ]
water: insoluble | [form ]
Liquid | [color ]
Clear | [Odor]
Characteristic aromatic odor | [Stability:]
Stable. Incompatible with strong oxidizing agents. Combustible. | [explosive limit]
6.6%, 150°F | [Water Solubility ]
INSOLUBLE | [λmax]
λ: 308 nm Amax: 1.00
λ: 310 nm Amax: 0.50
λ: 350 nm Amax: 0.05
λ: 375-400 nm Amax: 0.01 | [Detection Methods]
GC,NMR | [Merck ]
14,9631 | [BRN ]
956819 | [Henry's Law Constant]
0.997 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) | [Dielectric constant]
2.2400000000000002 | [Exposure limits]
NIOSH REL: TWA ceiling 5 ppm (40 mg/m3); ACGIH TLV: ceiling 5 ppm
(adopted). | [LogP]
4.28 | [CAS DataBase Reference]
120-82-1(CAS DataBase Reference) | [NIST Chemistry Reference]
Benzene, 1,2,4-trichloro-(120-82-1) | [EPA Substance Registry System]
120-82-1(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,N,Xi,T,F | [Risk Statements ]
R22:Harmful if swallowed.
R38:Irritating to the skin.
R50/53:Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
R52/53:Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
R39/23/24/25:Toxic: danger of very serious irreversible effects through inhalation, in contact with skin and if swallowed .
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed .
R11:Highly Flammable. | [Safety Statements ]
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) .
S37/39:Wear suitable gloves and eye/face protection .
S60:This material and/or its container must be disposed of as hazardous waste .
S61:Avoid release to the environment. Refer to special instructions safety data sheet .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S36/37:Wear suitable protective clothing and gloves .
S16:Keep away from sources of ignition-No smoking . | [RIDADR ]
UN 2321 6.1/PG 3
| [WGK Germany ]
3
| [RTECS ]
DC2100000
| [Autoignition Temperature]
571 °C | [Hazard Note ]
Irritant | [TSCA ]
Yes | [HazardClass ]
6.1 | [PackingGroup ]
III | [HS Code ]
29036990 | [Safety Profile]
Poison 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. | [Hazardous Substances Data]
120-82-1(Hazardous Substances Data) | [Toxicity]
LD50 orally in Rabbit: 550 mg/kg LD50 dermal Rat 6139 mg/kg |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
Sodium hydroxide-->Calcium hydroxide-->CALCIUM CARBONATE-->1,2,3-Trichlorobenzene-->1,3,5-Trichlorobenzene-->HEROIN | [Preparation Products]
Anthraquinone-->Copper(II) phthalocyanine-->Tetrachlorvinphos-->Pigment Geen 7-->Naphthionic acid-->1,2,3-Trichlorobenzene-->1,3,5-Trichlorobenzene-->2,5-Dichlorobenzoic acid-->1,2-NAPHTHALIC ANHYDRIDE-->Tetradifon-->2,4,5-Trichloroaniline-->HEXACHLOROBENZENE-->1,2,4-Trichloro-5-nitrobenzene-->Trichloroacetyl isocyanate-->N-propyl-N-[2-(2，4，6-trichloro phenoxy ethyl)carbamyl chloride]-->1-BROMO-2,4-DICHLOROBENZENE-->2,2',3,4,4',5,5'-HEPTACHLOROBIPHENYL-->1-IODO-2,4,5-TRICHLOROBENZENE |
| Hazard Information | Back Directory | [General Description]
Colorless liquid or white solid with a sharp chlorobenzene odor. Melting point 16.95°C (62.5°F) . | [Reactivity Profile]
1,2,4-TRICHLOROBENZENE(120-82-1) can react vigorously with oxidizing materials . Yields hydrogen chloride and phosgene when heated to decomposition [USCG, 1999]. | [Air & Water Reactions]
Insoluble in water. | [Health Hazard]
Exposures 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. | [Potential Exposure]
1,2,4-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. | [First aid]
If this chemical gets into the eyes, remove any contact lenses at once and irrigate immediately for at least 15 minutes, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts the skin, remove contaminated clothing and wash immediately with soap and water. Seek medical attention immediately. If this chemical has been inhaled, remove from exposure, begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if heart action has stopped. Transfer promptly to a medical facility. When this chemical has been swallowed, get medical attention. Give large quantities of water. Do not make an unconscious person vomit. | [Shipping]
UN2321 Trichlorobenzenes, liquid, Hazard Class: 6.1; Labels: 6.1-Poisonous materials. | [Incompatibilities]
Reacts violently with oxidants, acids, acid fumes; steam. | [Description]
Trichlorobenzenes (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 Properties]
1,2,4-Trichlorobenzene is a low-melting solid or liquid with a pleasant, aromatic odor. The Odor Threshold is 1.4 ppm. | [Chemical Properties]
Colorless, stable liquid; odor similar
to that of o-dichlorobenzene. Miscible with
most organic solvents and oils; insoluble in water.
Combustible. | [Waste Disposal]
Incineration, 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. | [Physical properties]
Colorless liquid with an odor similar to o-dichlorobenzene. Odor threshold concentration is 1.4
(quoted, Amoore and Hautala, 1983). | [Uses]
1,2,4-Trichlorobenzene is a solvent in various organic chemical reactions. | [Uses]
Trichlorobenzenes are primarily used as solvents in chemical
manufacturing industries. 1,2,4-Trichlorobenzene is economically
the most important isomer. 1,2,4-Trichlorobenzene is
used as a solvent in chemical reactions to dissolve oils, waxes,
and resins. Furthermore, it is also used as a dye carrier. 1,2,3-
Trichlorobenzene is used as an intermediate for pesticides
production, pigments, and dyes. 1,3,5-Trichlorobenzene is not
marketed commercially and has very limited use as a chemical
intermediate. Besides, trichlorobenzenes can also be used as
degreasing agents, as septic tanks and drain cleaners, and as an
ingredient in wood preservatives and abrasive formulations.
Other minor uses include metal work, anticorrosive paint, and
corrosion inhibitor in sprays. In the past, mixed isomers of
trichlorobenzenes were used to control termites; however, their
use has been discontinued. | [Application]
Trichlorobenzenes 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 | [Definition]
ChEBI: A trichlorobenzene with chloro substituents at positions 1, 2 and 4. | [Synthesis Reference(s)]
Journal of the American Chemical Society, 74, p. 3890, 1952 DOI: 10.1021/ja01135a052 | [Environmental Fate]
Biological. 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). | [Purification Methods]
Separate 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 evaluation]
The 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. |
| Spectrum Detail | Back Directory | [Spectrum Detail]
1,2,4-Trichlorobenzene(120-82-1)MS
1,2,4-Trichlorobenzene(120-82-1)1HNMR
1,2,4-Trichlorobenzene(120-82-1)13CNMR
1,2,4-Trichlorobenzene(120-82-1)IR1
1,2,4-Trichlorobenzene(120-82-1)Raman
|
| Well-known Reagent Company Product Information | Back Directory | [Acros Organics]
1,2,4-Trichlorobenzene, 99+%(120-82-1) | [Alfa Aesar]
1,2,4-Trichlorobenzene, Spectrophotometric Grade, 99% min(120-82-1) | [Sigma Aldrich]
120-82-1(sigmaaldrich) | [TCI AMERICA]
1,2,4-Trichlorobenzene,>98.0%(GC)(120-82-1) |
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