3883-13-4

Usage

Uses

Used in Chemical Production:
(2,2,2-Trichloroethyl)benzene is used as an intermediate in the production of various chemicals such as dyes, pigments, and pharmaceuticals.
Used in Solvent Applications:
(2,2,2-Trichloroethyl)benzene is used as a solvent for cellulose ethers, oils, and resins.
Used in Environmental and Health Management:
(2,2,2-Trichloroethyl)benzene is considered a hazardous substance due to its toxic effects on the environment and human health. It is listed as a hazardous air pollutant and a hazardous waste in some regions, requiring careful management of its use and disposal to minimize its impact on the environment and human health.

Upstream product

• 56-23-5 tetrachloromethane 
• 53617-91-7 C₁₁H₁₉N₂OP 
• 41139-88-2 Phenylacetyl-triphenylsilan 
• 67-66-3 chloroform 
• 100-44-7 benzyl chloride 
• 2547-61-7 Trichloromethanesulfonyl chloride 
• 75-62-7 Bromotrichloromethane 
• 100-39-0 benzyl bromide 
• 75-35-4 1,1-Dichloroethylene 
• 100-34-5 benzene diazonium chloride 
• 17876-99-2 (4-chlorobenzyl)trimethylsilane 
• 68307-67-5 2-chloro[(trimethylsilyl)methyl]benzene 
• 100-51-6 benzyl alcohol 
• 108-88-3 toluene 

Downstream Products

• 698-88-4 (2,2-dichlorovinyl)benzene 
• 4412-39-9 (2,2-dichloroethyl)benzene 
• 104415-94-3 1-Butyl-3-chloro-1,4-dihydro-naphthalene 
• 104415-91-0 (2,2,4-Trichloro-octyl)-benzene 
• 104415-93-2 1-Butyl-3-chloro-1,2-dihydro-naphthalene 
• 104415-96-5 2-chloro-1-phenyl-1,3-octadiene 
• 104415-95-4 ((E)-2,4-Dichloro-oct-1-enyl)-benzene 
• 104415-89-6 1-Butyl-3,3-dichloro-1,2,3,4-tetrahydro-naphthalene 
• 104415-92-1 2-chloro-4-methylnaphthalene 
• 104415-90-9 (2,2,4,4-Tetrachloro-pentyl)-benzene 
• 139489-24-0 (2,2-Dichloro-2-thiocyanato-ethyl)-benzene 
• 65792-04-3 C₁₆H₁₄Cl₄S 
• 393827-56-0 3-chloro-3-phenyl-prop-2(Z)-en-1-ol 
• 4604-28-8 (Z)-β-chlorostyrene 

Relevant academic research and scientific papers

Singlet vs Triplet Reactivity of Photogenerated α,n-Didehydrotoluenes

The reactivity of α,n-didehydrotoluenes (DHTs) in protic media (organic/aqueous mixtures) was explored by means of a combined computational and experimental approach. These intermediates were generated via a photoinduced double elimination process occurring in (chlorobenzyl)trimethylsilanes and led to the formation of a varied products distribution, depending on the isomer tested. Irradiation of ortho- and para-derivatives resulted, respectively, in the formation of triplet α,2- and α,4-DHTs, whose diradical reactivity led to both radical and polar products. On the other hand, irradiation of the meta-precursor led to the singlet α,3-DHT isomer. The latter showed a marked preference for the formation of polar products and this was rationalized, as supported by computational evidence, via the involvement of a zwitterionic species arising through interaction of the nucleophilic solvent with the benzylic position of the DHT.

A convenient synthesis of (Z)-1-chloro-1-alkenes and (Z)-1-chloro-2-alkoxy-1-alkenes

Mild, room temperature CrCl2 reduction of 1,1,1-trichloroalkanes stereoselectively generates (Z)-1-chloro-2-substituted-1-alkenes in excellent yields.

Use of Sacrificial Anodes in Electrochemical Functionalization of Organic Halides

This article reviews the new possibilities in organic synthesis offered by the electroreduction of organic halides in the presence of various electrophiles using sacrificial metallic anodes.

ABSOLUTE RATES AND SELECTIVITY OF HOMOLYTIC SUBSTITUTION AT A CARBON ATOM IN BENZYL COMPLEXES OF COBALT. EFFECT OF AXIAL LIGANDS

The absolute rate constants were determined for the bimolecular homolytic substitution of organocobalt groups by a trichloromethyl radical in the benzylglyoxime complexes of cobalt, and the effect of axial and equatorial ligands on the reaction rate was studied.The change in the dissociation energy of the cobalt-carbon bond has a determining effect on the substitution rate.The relation between the reactivity and selectivity with variation of the axial ligand is inverse in nature.

Electrochemical Cross-Coupling of Alkyl Halides in the Presence of a Sacrificial Anode

The electrochemical trichloromethylation of various alkyl halides has been obtained in high yields in an undivided cell in the presence of a sacrificial anode.This cross-coupling process has been extended to the preparation of numerous gem-dichloro compounds from trichloro-substituted methanes and alkyl halides.Zinc,magnesium or aluminium were used as anodes according to the reduction potentiel of the reagents.Mixtures of polar aprotic solvents,e.g.THF-TMU or THF-NMP, were found more appropriate than pure solvents.The critical role of the metallic ions from the consumption of the anode has been clearly evidenced.

EFFECT OF STRUCTURAL FACTORS ON RATE OF BIMOLECULAR HOMOLYTIC SUBSTITUTION AT A CARBON ATOM IN BENZYL COMPLEXES OF COBALT

The reaction of the benzylglyoximate complexes of cobalt with bromotrichloromethane leads to the formation of 1,1,1-trichloro-2-arylethanes, which correspond to bimolecular homolytic substitution of the cobalt-containing group by the trichloromethyl radic

ELECTROCHEMICAL CROSS-COUPLING OF ORGANIC HALIDES: TRICHLORMETHYLATION AND RELATED SYNTHESIS OF GEM-DICHLORO COMPOUNDS

The cross-coupling of activated alkyl halides with carbon tetrachloride or substituted trichloromethanes can be obtained electrochemically in good yield in an undivided cell with a sacrificial anode.

HOMOLYTIC DISPLACEMENT AT CARBON VI. SYNTHESIS OF TRICHLOROETHYLARENES FROM BENZYLCOBALOXIMES

Benzylbis(dimethylglyoximato)pyridinecobalt(III) reacts with bromotrichloromethane at from 50 to 90 deg C in chloroform to give good yields of trichloroethylbenzene, which are higher when imidazole is present in the reaction mixture.Methyl- and polymethyl-substituted benzylbis(dimethylglyximato)pyridinecobalt(III) complexes give higher yields of the corresponding trichloroethylarenes (85-90percent), whereas 4-chlorobenzylbis(dimethylglyoximato)pyridinecobalt(III) only gives the 4-nitro-trichloroethylarene when imidazole is present during the reaciton.Similar reactions were observed with benzylcobaloximes and trichloromethanesulphonyl chloride both thermally and under irradiation by tungsten lamps through all-pyrex apparatus.The reactions are interpreted as a direct attack of the trichloromethyl radical on the α-carbon of the benzyl ligand.