108-70-3 Usage
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
white to beige crystalline powder
Uses
Different sources of media describe the Uses of 108-70-3 differently. You can refer to the following data:
1. 1,3,5-Trichlorobenzene is used for someof these
applications plus as a termite preparation and insecticide.
These compounds are found as unintended by-products of
the manufacture of the mono- and dichlorobenzenes.
2. 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.
3. 1,3,5-Trichlorobenzene is an isomer of 1,2,4-Trichlorobenzene (T774220) which is a solvent in various organic chemical reactions.
General Description
White to off-white crystals.
Air & Water Reactions
Insoluble in water.
Reactivity Profile
Can react vigorously with oxidizing materials. .
Fire Hazard
1,3,5-Trichlorobenzene is combustible.
Safety Profile
Moderately toxic by
ingestion and intraperitoneal routes.
Mutation data reported. When heated to
decomposition it emits toxic vapors of Cl-.
Environmental fate
Biological. Under aerobic conditions, soil microbes degraded 1,3,5-trichlorobenzene to 1,3- and
1,4-dichlorobenzene and carbon dioxide (Kobayashi and Rittman, 1982). A mixed culture of soil
bacteria or a Pseudomonas sp. transformed 1,3,5-trichlorobenzene to 2,4,6-trichlorophenol
(Ballschiter and Scholz, 1980).
In an enrichment culture derived from a contaminated site in Bayou d’Inde, LA, 1,3,5-
trichlorobenzene underwent reductive dechlorination yielding 1,3-dichlorobenzene. The maximum
dechlorination rate, based on the recommended Michaelis-Menten model, was 9.5 nM/d
(Pavlostathis and Prytula, 2000).
Photolytic. The sunlight irradiation of 1,3,5-trichlorobenzene (20 g) in a 100-mL borosilicate
glass-stoppered Erlenmeyer flask for 56 d yielded 160 ppm pentachlorobiphenyl (Uyeta et al.,
1976). A photooxidation half-life of 6.17 months was reported for the vapor-phase reaction of
1,3,5-trichlorobenzene with OH radicals (Atkinson, 1985).
Purification Methods
Recrystallise it from dry *benzene or toluene. [Beilstein 5 IV 666.]
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.
Check Digit Verification of cas no
The CAS Registry Mumber 108-70-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 8 respectively; the second part has 2 digits, 7 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 108-70:
(5*1)+(4*0)+(3*8)+(2*7)+(1*0)=43
43 % 10 = 3
So 108-70-3 is a valid CAS Registry Number.
InChI:InChI=1/C6H3Cl3/c7-4-1-5(8)3-6(9)2-4/h1-3H
108-70-3Relevant articles and documents
Effects of FeS on the transformation kinetics of γ-hexachlorocyclohexane
Liu, Xiangmei,Peng, Ping'an,Fu, Jiamo,Huang, Weilin
, p. 1822 - 1828 (2003)
Distinctly different rates and pathways were observed for abiotic transformation of γ-hexachlorocyclohexane (γHCH) between homogeneous systems and systems containing FeS solid. The observed half-lives of γ-HCH decrease from about 1136 and 126 d in homogen
Chlorination of aniline and methyl carbanilate by N-chlorosuccinimide and synthesis of 1,3,5-trichlorobenzene
Davis, Matthew C.
, p. 1100 - 1108 (2009)
Aniline undergoes regioselective trichlorination by N-chlorosuccinimide (NCS) in acetonitrile in good yield. The product 2,4,6-trichoroaniline was converted into 1,3,5-trichlorobenzene by reduction of its diazonium salt. Reaction of the methyl carbamate of aniline with NCS gave only the 2,4-dichlorophenyl carbamate. Copyright Taylor & Francis Group, LLC.
Electroreductive dechlorination of α-hexachlorocyclohexane catalyzed by iron porphyrins in nonaqueous media
Zhu, Weihua,Ni, Cui,Liang, Lili,Li, Junwen,Li, Minzhi,Ou, Zhongping,Kadish, Karl M.
, p. 519 - 527 (2014)
Two iron porphyrins, (TPP)FeCl and (OEP)FeCl, where TPP and OEP are the dianions of tetraphenylporphyrin and octaethylporphyrin, respectively, were utilized as catalysts for the electroreductive dechlorination of α-hexachlorocyclohexane (α-HCH) which was monitored by electrochemistry, in situ UV-visible spectroelectrochemistry and controlled potential electrolysis in N,N′-dimethylformamide. GC-MS analysis of the α-HCH degradation products revealed the stepwise formation of pentachlorocyclohexene and tetrachlorocyclohexadiene as intermediates, prior to generation of the final dechlorination products which consisted of an isomeric mixture of trichlorobenzenes. Based on identification of the intermediates and final products in the reaction, an overall dechlorination mechanism of α-hexachlorocyclohexane is proposed.
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Hodgson,Mahadevan
, p. 173 (1947)
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Dadieu,Pongratz,Kohlrausch
, p. 426,438 (1932)
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Iron(iii)porphyrin electrocatalyzed enantioselective carbon-chloride bond cleavage of hexachlorocyclohexanes (HCHs): Combined experimental investigation and theoretical calculations
Liang, Xu,Li, Minzhi,Mack, John,Lobb, Kevin,Zhu, Weihua
, p. 11470 - 11476 (2018)
Enantioselective electrocatalysis of α-, β-, γ- and δ-hexachlorocyclohexanes (HCHs) by tetrakis-pentafluorophenyl-Fe(iii)porphyrin is described. The first example of the combined use of electrochemical measurements and theoretical calculations to determine the mechanism of the enantioselective C-Cl bond cleavage of the electrocatalysis is reported. The electrochemical measurements demonstrate that the reactivity of the HCHs follows the order γ-HCH > α-HCH > δ-HCH > β-HCH. Steric considerations and a molecular orbital theory approach can be used to rationalize the enantioselective nature of the catalysis based on the ease of approach of each Cl atom to the central Fe(i) ion and a consideration of the nodes on the C-Cl bonds that weaken these bonds in a manner that results in bond cleavage and the formation of an Fe-Cl bond.
Visible light driven hydro-/deuterodefunctionalization of anilines
Majek, Michal,Filace, Fabiana,Von Wangelin, Axel Jacobi
supporting information, p. 4518 - 4522 (2015/03/18)
The defunctionalization of anilines is an important strategy in aromatic-substitution chemistry. Herein, we report on visible light mediated hydro- and deuterodediazonations in solutions of DMF. The mild reaction conditions (DMF, RT, no additives) tolerate various functional groups and allow the site-specific introduction of D atoms to the arene. Mechanistic investigations indicate the participation of photoredox and radical chain pathways and competing abstraction of methyl and formyl hydrogen atoms from DMF.
