634-90-2

Usage

Uses

Used in Chemical Industry:
1,2,3,5-TETRACHLOROBENZENE is used as an intermediate for the production of various chemicals, such as dyes, pesticides, and pharmaceuticals. Its unique structure allows it to be a versatile building block in the synthesis of these compounds.
Used in Plastics and Rubber Industry:
1,2,3,5-TETRACHLOROBENZENE is used as an additive in the plastics and rubber industry to enhance the properties of the materials, such as improving their resistance to heat, light, and chemicals.
Used in Pharmaceutical Industry:
1,2,3,5-TETRACHLOROBENZENE is used as a starting material for the synthesis of certain pharmaceutical compounds, taking advantage of its specific chemical structure to create drugs with desired therapeutic properties.
Used in Dye Industry:
1,2,3,5-TETRACHLOROBENZENE is used as a precursor in the production of various dyes, particularly those with specific color properties and stability.
Used in Pesticide Industry:
1,2,3,5-TETRACHLOROBENZENE is used as a component in the formulation of certain pesticides, leveraging its chemical properties to enhance the effectiveness of these products in controlling pests.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Simple aromatic halogenated organic compounds, such as 1,2,3,5-Tetrachlorobenzene , are very unreactive. Reactivity generally decreases with increased degree of substitution of halogen for hydrogen atoms. Materials in this group may be incompatible with strong oxidizing and reducing agents. Also, they may be incompatible with many amines, nitrides, azo/diazo compounds, alkali metals, and epoxides. 1,2,3,5-Tetrachlorobenzene may react with oxidizers. .

Health Hazard

ACUTE/CHRONIC HAZARDS: 1,2,3,5-Tetrachlorobenzene may cause irritation on contact.

Fire Hazard

1,2,3,5-Tetrachlorobenzene is probably combustible.

Environmental fate

Biological. A mixed culture of soil bacteria or a Pseudomonas sp. transformed 1,2,3,5-tetrachlorobenzene to 2,3,4,6-tetrachlorophenol (Ballschiter and Scholz, 1980). The half-life of 1,2,3,5- tetrachlorobenzene in an anaerobic enrichment culture was 1.8 d (Beurskens et al., 1993). In an enrichment culture derived from a contaminated site in Bayou d’Inde, LA, 1,2,3,5- tetrachlorobenzene underwent reductive dechlorination to 1,2,4- and 1,3,5-trichlorobenzene at relative molar yields of 7 and 93%, respectively. The maximum dechlorination rate, based on the recommended Michaelis-Menten model, was 94 nM/d (Pavlostathis and Prytula, 2000). Photolytic. Irradiation (λ ≥285 nm) of 1,2,3,5-tetrachlorobenzene (1.1–1.2 mM/L) in an acetonitrile-water mixture containing acetone (0.553 mM/L) as a sensitizer gave the following products (% yield): 1,2,3-trichlorobenzene (5.3), 1,2,4-trichlorobenzene (4.9), 1,3,5-trichlorobenzene (49.3), 1,3-dichlorobenzene (1.8), 2,3,4,4′,5,5′,6-heptachlorobiphenyl (1.41), 2,2′,3,4,4′,6,6′- heptachlorobiphenyl (1.10), 2,2′,3,3′,4,5′,6-heptachlorobiphenyl (4.50), four hexachlorobiphenyls (4.69), one pentachlorobiphenyl (0.64), trichloroacetophenone, 1-(trichlorophenyl)-2-propanone, and (trichlorophenyl)acetonitrile (Choudhry and Hutzinger, 1984). Without acetone, the identified photolysis products (% yield) included 1,2,3-trichlorobenzene (trace), 1,2,4-trichlorobenzene (24.3), 1,3,5-trichlorobenzene (11.7), 1,3-dichlorobenzene (0.5), 1,4-dichlorobenzene (3.3), pentachlorobenzene (1.43), 1,2,3,4-tetrachlorobenzene (5.99), two heptachlorobiphenyls (1.40), two hexachlorobiphenyls (<0.01), and one pentachlorobiphenyl (0.75) (Choudhry and Hutzinger, 1984).

Purification Methods

Crystallise it from EtOH. [Beilstein 5 II 157, 5 III 551, 5 IV 668.]

Upstream product

• 88-88-0 2,4,6-trinitrochlorobenzene 
• 1890-41-1 optically inactive 1,2,3,4,5,6-hexachloro-cyclohexene 
• 127-63-9 diphenyl sulphone 
• 609-20-1 2,6-dichloro-p-phenylenediamine 
• 634-91-3 3,4,5-trichloroaniline 
• 71-43-2 benzene 
• 95-94-3 1,2,4,5-tetrachlorobenzene 
• 608-93-5 pentachlorobenzene 
• 78921-26-3 bis(2,3,5-trichlorophenyl)mercury 
• 78921-27-4 bis(3,4,5-trichlorophenyl)mercury 
• 118-74-1 hexachlorobenzene 
• 7705-08-0 iron(III) chloride 
• 88-06-2 2,4,6-Trichlorophenol 
• 7719-12-2 phosphorus trichloride 

Downstream Products

• 107533-18-6 2-ethyl-1,3,4,5-tetrachloro-benzene 
• 50402-31-8 1,3-diethyl-2,4,5,6-tetrachloro-benzene 
• 933-78-8 2,3,5-trichlorophenol 
• 54135-81-8 2,3,5-trichloroanisole 
• 3714-62-3 2,3,4,6-tetrachloronitrobenzene 
• 56892-56-9 2,3,4,6-tetrachloroiodobenzene 
• 28073-03-2 1,2,3,5-tetrachloro-4,6-dinitrobenzene 
• 40707-32-2 2,3,4,6-tetrachloro-benzenesulfonic acid 
• 876498-70-3 4H-nonachloro-cyclohexene 
• 109707-43-9 1,2,3,5-tetrachloro-4,6-diiodo-benzene 
• 859819-48-0 1H,3H-decachloro-cyclohexane 
• 2136-96-1 1,2,3,5-tetrachloro-4,6-bis-dichloromethyl-benzene 
• 126278-82-8 2,3,4,6-tetrachloro-1-(trifluoromethyl)benzene 
• 89165-38-8 Octyl 2,3,5-trichlorophenyl sulfide 

Relevant academic research and scientific papers

PROCESS FOR THE PREPARATION OF ORGANIC HALIDES

The present invention provides a halo-de-carboxylation process for the preparation of organic chlorides, organic bromides and mixtures thereof, from their corresponding carboxylic acids, using a chlorinating agent selected from trichloroisocyanuric acid (TCCA), dichloroisocyanuric acid (DCCA), or combination thereof, and a brominating agent.

Reactions of 2,4,6-trichlorophenol on model fly ash: Oxidation to CO and CO2, condensation to PCDD/F and conversion into related compounds

Thermal treatment of 2,4,6-trichlorophenol on a magnesium silicate-based model fly ash in the temperature range between 250°C and 400°C leads predominantly to carbon monoxide and carbon dioxide. The fraction of 2,4,6-trichlorophenol which is oxidized to CO and CO2 increases from 3% at 250°C to 75% at 400°C. Further products are polychlorinated benzenes, dibenzo-p-dioxins, dibenzofurans and phenols. The homologue and isomer patterns of the chlorobenzenes suggest chlorination in the ipso-position of the trichlorophenol. The formation of PCDD from 2,4,6-trichlorophenol and 2,3,4,6-tetrachlorophenol on municipal solid waste incinerator fly ashes and model fly ash were compared and the reaction order calculated.

Identification of surrogate compounds for the emission of PCDD/F (I-TEQ value) and evaluation of their on-line realtime detectability in flue gases of waste incineration plants by REMPI-TOFMS mass spectrometry

Correlations between products of incomplete combustion (PIC), e.g., chloroaromatic compounds, can be used to characterise the emissions from combustion processes, like municipal or hazardous waste incineration. A possible application of such relationships may be the on-line real-time monitoring of a characteristic surrogate, e.g., with Resonance-Enhanced Multiphoton Ionization-Time-of-Flight Mass Spectrometry (REMPI-TOFMS). In this paper, we report the relationships of homologues and individual congeners of chlorinated benzenes (PCBz), dibenzo-p-dioxins (PCDD), dibenzofurans (PCDF) and phenols (PCPh) to the International Toxicity Equivalent (I-TEQ) of the PCDD/F (I-TEQ value) in the flue gas and stack gas of a 22 MW hazardous waste incinerator (HWI). As the REMPI detection sensitivity is decreasing with the increase of the degree of chlorination, this study focuses on the lower chlorinated species of the compounds mentioned above. Lower chlorinated species, e.g., chlorobenzene (MCBz), 1,4-dichlorobenzene, 2,4,6-trichlorodibenzofuran or 2,4-dichlorophenol, were identified as I-TEQ surrogates in the flue gas. In contrast to the higher chlorinated phenols, the lower chlorinated phenols (degree of chlorination 4) were not reliable as surrogates in the stack gas. The identified surrogates are evaluated in terms of their detectability by REMPI-TOFMS laser mass spectrometry. The outcome is that MCBz is the best suited surrogate for (indirect) on-line measuring of the I-TEQ value in the flue gas by REMPI-TOFMS. The correlation coefficient r of the MCBz concentration to the I-TEQ in the flue gas was 0.85.

Photoinduced Charge Separation in Rigid Bichromophoric Compounds and Charge Transfer State Electron Transfer Reactivity

Bichromophoric compounds giving, after photoexcitation, a locally excited state (LE) rapidly followed by an intramolecular charge transfer (CT) state were designed using a Paddon-Row type synthesis.The electron-accepting end of the CT state is chosen in order to play the role of an electron relay versus external acceptors.In this way, electron transfer photosensitization is made available by using the CT state of bichromophores.The photophysics of the synthesized bichromophores is discussed, and the reductive dechlorination of polychlorinated benzenes is used as a test reaction.The bichromophoric sensitizer is unexpectedly found to be totally regenerated: the reaction is shown to be initiated by an electron transfer from the CT state to the chlorinated quencher.A rapidly breaking radical anion leads to the dechlorination, while the recombination of the sensitizer radical cation with the released chloride anion opens the way to the sensitizer recovery.

Photodechlorination of polychlorobenzene congeners in surfactant micelle solutions

Photochemical reactions of polychlorobenzene congeners in aqueous solutions containing surfactant micelles have been investigated. Photoreduction through photodechlorination was shown to be the main decay pathway in which lesser chlorinated congeners and benzene were formed as intermediates. Final products included H+ and Cl- in approximately stoichiometric amounts. Several hydrogen sources were investigated with sodium borohyride shown to be a promising rate enhancer at elevated concentrations. -Authors

Dechlorination of chlorinated benzenes by an anaerobic microbial consortium that selectively mediates the thermodynamic most favorable reactions

A chlorinated benzene dechlorinating anaerobic microbial consortium was obtained by selective enrichment with hexachlorobenzene (HCB) and lactate from a freshwater sediment sample that originated from an area with proven in situ HCB dechlorination. The consortium was used to determine compound selectivity and relative dechlorination rates by incubation with the individual chlorinated benzenes under methanogenic conditions. The selectivity of the enrichment culture showed an interesting correlation with the thermodynamics of the various dechlorination steps: from the 19 dechlorination reactions possible with benzenes that contain at least two chlorines, only the seven reactions with the highest energy release took place. -from Authors

DEHALOGENATION OF CHLOROBENZENES WITH SODIUM DIHYDRIDOBIS(2-METHOXYETHOXO)ALUMINATE

The dehalogenation of a series of 9 mono- to pentachlorinated benzenes with the title hydride in toluene has been found to be first order in the substrate and half order in the hydride.The reactivities of the chlorobenzenes, expressed by rate constants for the first-step dehalogenation, increased with increasing number of chlorine atoms over three orders of magnitude.The rate data revealed the unexpected acceleration of benzene formation during exhaustive dehalogenation of the higher chlorinated benzenes.For comparison, dehalogenation of several isomeric dibromobenzenes and bromochlorobenzenes with the same hydride and the product distribution for the dehalogenation of some chlorobenzenes with LiAlH4 are also reported.

Photochemistry of Polyhaloarenes. 12. The Photochemistry of Pentachlorobenzene in Micellar Media

The dependence of the reciprocal of the quantum yield for the photohydrodechlorination of pentachlorobenzene (1) in aqueous 0.100 M hexadecyltrimethylammonium bromide (CTAB) solution upon the reciprocal of the microconcentration of 1 and upon the reciprocal of the probability for excited state 1 reacting with ground-state 1 provides a linear correlation at high microconcentrations of 1.The regiochemistry of the photohydrodechlorination process in CTAB favors formation of 1,2,4,5-tetrachlorobenzene to a significantly smaller extent than is observed in the analogous process in acetonitrile solution in the presence of triethylamine.The bromotetrachlorobenzene byproduct is formed in the photolysis in the following composition: 1-bromo-2,3,4,5-tetrachloro- (5) : 2-bromo-1,3,4,5-tetrachloro- (6) : 3-bromo-1,2,4,5-tetrachlorobenzene (7) = 9.7 : 66.7 : 23.3.In a trapping experiment carried out during an irradiation of 1 in CH3CN/ H2O (8:2) in the presence of excess KBr at 254 nm, bromotetrachlorobenzenes (5:6:7) were formed in a ratio of 11.3 : 66.8 : 21.9.These experiments are rationalized by proposing that product in these micellar photohydrodechlorination reactions is formed by fission of triplet-state 1 and a competing process which involves conversion of triplet-state 1 to triplet excimer which then undergoes fragmentation.

Photochemistry of Polyhaloarenes. 8. The Photodechlorination of Pentachlorobenzene

Measurements of the intersystem crossing yield of pentachlorobenzene triplet, the quenching of photodechlorination of pentachlorobenzene with fumaronitrile, the dependence of the fluorescence lifetime, and the quantum yield of photodechlorination of pentachlorobenzene upon substrate concentration and the dependence of relative product concentration upon light intensity provide evidence for three pathways to product: direct fission of singlet and triplet and fragmentation of triplet excimer.

Photochemistry of Polyhaloarenes. 7. Photodechlorination of Pentachlorobenzene in the Presence of Sodium Borohydride

The mechanism of photodechlorination of pentachlorobenzene (1) in acetonitrile has been examined.The quantum yield of reaction (Φr) has been found to vary with the concentration of 1.A charge-transfer intermediate formed from the triplet excited state of 1 is proposed to explain the observations. Φr increases with added NaBH4 and 1/Φr varies directly with the inverse of the concentration of the electron-transfer reagent.The regiochemistry deuterium isotope effects, tracer studies, and quenching analyses are consistent with an electron-transfer process.