634-66-2 Usage
Chemical Properties
WHITE CRYSTALLINE SOLID
Uses
Different sources of media describe the Uses of 634-66-2 differently. You can refer to the following data:
1. Component of dielectric fluids, synthesis.
2. 1,2,3,4-tetrachlorobenzene was used as a model compound to determine the chlorobenzenes (CBs) in soil samples. It was also used for rapid dechlorination of 1,2,3,4-tetrachlorodibenzo-p-dioxin (1,2,3,4-TeCDD).
Definition
ChEBI: A tetrachlorobenzene carrying chloro groups at positions 1, 2 , 3 and 4.
Air & Water Reactions
Insoluble in water.
Reactivity Profile
Simple aromatic halogenated organic compounds, such as 1,2,3,4-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.
Health Hazard
ACUTE/CHRONIC HAZARDS: 1,2,3,4-Tetrachlorobenzene may cause irritation of the skin.
Fire Hazard
1,2,3,4-Tetrachlorobenzene is probably combustible.
Safety Profile
Moderately toxic by ingestion. An experimental teratogen. Experimental reproductive effects. Irritant. Combustible liquid. When heated to decomposition it emits toxic fumes of Cl-. See also CHLORINATED HYDROCARBONS, AROMATIC.
Environmental fate
Biological. A mixed culture of soil bacteria or a Pseudomonas sp. transformed 1,2,3,4-
tetrachlorobenzene to 2,3,4,5-tetrachlorophenol (Ballschiter and Scholz, 1980). After incubation in
sewage sludge for 32 d under anaerobic conditions, 1,2,3,4-tetrachlorobenzene did not biodegrade
(Kirk et al., 1989). The half-life of 1,2,3,4-tetrachlorobenzene in an anaerobic enrichment culture
was 26.4 h (Beurskens et al., 1993). Potrawfke et al. (1998) reported that a pure culture of
Pseudomonas chlororaphis RW71 mineralized 1,2,3,4-tetrachlorobenzene as a sole source of
carbon and energy. Intermediate biodegradation products identified were tetrachlorocatechol,
tetrachloromuconic acid, 2,3,5-trichlorodienelactone, 2,3,5-trichloro-4-hydroxymuconic acid.
In an enrichment culture derived from a contaminated site in Bayou d’Inde, LA, 1,2,4,5-
tetrachlorobenzene underwent reductive dechlorination yielding 1,2,4-trichlorobenzene. The
maximum dechlorination rate, based on the recommended Michaelis-Menten model, was 208
nM/d (Pavlostathis and Prytula, 2000).
Photolytic. Irradiation (λ ≥285 nm) of 1,2,3,4-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 (9.2), 1,2,4-trichlorobenzene (32.6), 1,3-dichlorobenzene
(5.2), 1,4-dichlorobenzene (1.5), 2,2′,3,3′,4,4′,5-heptachlorobiphenyl (2.52), 2,2′,3,3′,4,5,6′-
heptachlorobiphenyl (1.22), 10 hexachlorobiphenyls (3.50), five pentachlorobiphenyls (0.87),
dichlorophenyl cyanide, two trichloroacetophenones, trichlorocyanophenol, (trichlorophenyl)
acetonitriles, and 1-(trichlorophenyl)-2-propanone (Choudhry and Hutzinger, 1984). Without
acetone, the identified photolysis products (% yield) included 1,2,3-trichlorobenzene (7.8), 1,2,4-
trichlorobenzene (26.8), 1,2-dichlorobenzene (0.5), 1,3-dichlorobenzene (0.7), 1,4-dichloro-benzene
(30.4), 1,2,3,5-tetrachlorobenzene (2.26), 1,2,4,5-tetrachlorobenzene (0.72), 2,2′,3,3′,4,4′,5-
heptachlorobiphenyl (<0.01), and 2,2′,3,3′,4,5,6′-heptachlorobiphenyl (<0.01) (Choudhry and
Hutzinger, 1984). The sunlight irradiation of 1,2,3,4-tetrachlorobenzene (20 g) in a 100-mL
borosilicate glass-stoppered Erlenmeyer flask for 56 d yielded 4,280 ppm heptachlorobiphenyl
(Uyeta et al., 1976).
Solubility in water
Soluble in acetic acid, ether, ligroin (Weast, 1986), and very soluble in many chlorinated solvents
including chloroform, carbon tetrachloride, etc.
Purification Methods
Crystallise it from EtOH. [Beilstein 5 H 204, 5 II 156, 5 III 550, 5 IV 667.]
Check Digit Verification of cas no
The CAS Registry Mumber 634-66-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,3 and 4 respectively; the second part has 2 digits, 6 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 634-66:
(5*6)+(4*3)+(3*4)+(2*6)+(1*6)=72
72 % 10 = 2
So 634-66-2 is a valid CAS Registry Number.
InChI:InChI=1/C6H2Cl4/c7-3-1-4(8)6(10)5(9)2-3/h1-2H
634-66-2Relevant articles and documents
Photoisomerisation of bicyclo[4.2.0]octadienes to tricyclo[4.2.0.02,5] octenes: Application to the synthesis of [n]ladderanes
Warrener,Pitt,Nunn,Kennard
, p. 621 - 624 (1994)
A new approach for the extension of [n]ladderanes is described which involves formation of an end-fused bicyclo[4.2.0]octadiene and its photoisomerisation to the related tricyclo[4.2.0.02,5] octene as the ladderane extension step. The protocol is illustrated with the synthesis of [3]ladderane (9) from an unsubstituted cyclobutene and nor[5]ladderane (13) from an ester activated cyclobutene. The exo-stereochemistry of (13) is confirmed by reference to intermediate (23) for which a single crystal X-Ray structure analysis was obtained.
Preparation method for 3,5,-dichloro-2,4,-difluoroaniline
-
, (2017/03/08)
The invention relates to the field of organic synthesis, specifically to a preparation method for 3,5,-dichloro-2,4,-difluoroaniline and application thereof. The preparation method for 3,5,-dichloro-2,4,-difluoroaniline provided by the invention comprises the following steps: 1) nitration reaction; 2) reduction reaction; 3) diazotization reaction; 4) nitration reaction; 5) fluorination reaction; and 6) reduction reaction. The preparation method for 3,5,-dichloro-2,4,-difluoroaniline provided by the invention has the following beneficial effects: 1) the method has mild reaction conditions, is stable and controllable, has less active sites, is insusceptible to side reaction, and has good yield and quality in the whole line; and 2) raw materials are cheap and easily available, so cost can be effectively reduced, and energy is saved; meanwhile, the use of chlorine gas is avoided, so the method is environment-friendly.
Reactions of 2,4,6-trichlorophenol on model fly ash: Oxidation to CO and CO2, condensation to PCDD/F and conversion into related compounds
Hell,Stieglitz,Altwicker,Addink,Will
, p. 697 - 702 (2007/10/03)
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.
Radiation induced catalytic dechlorination of hexachlorobenzene on oxide surfaces
Zacheis, George Adam,Gray, Kimberly A.,Kamat, Prashant V.
, p. 4715 - 4720 (2007/10/03)
Radiation induced catalytic dehalogenation of hexachlorobenzene (HCB) adsorbed to alumina (Al2O3), silica (SiO2), titania (TiO2), zirconia (ZrO2), and a commercially available zeolite has been studied using Cobalt-60 (60Co) as a radiation source. Solid-particulate samples were irradiated over a dose range of 0-58 kGy, and the chemical changes were monitored using Fourier transform infrared diffuse reflectance (FTIR-DR) and gas chromatography with electron capture detection (GC-ECD). The extent of HCB degradation on the metal oxides was found to increase dramatically in samples evacuated under vacuum, pointing to the competitive scavenging of conduction band electrons by surface adsorbed species, primarily oxygen. Coadsorbed water diminished HCB conversion on all oxides but to a greater degree on alumina. HCB degradation on metal oxides was found to be highly dependent upon the conduction band energy of the support material, thus confirming the occurrence of ultra-band-gap excitation and charge separation in irradiated oxides. Higher yields of dechlorination products were witnessed in alumina and silica samples. Zeolite, titania, and zirconia were also found to be inefficient in promoting radiation induced catalysis. The absence of oxidation products in the irradiated HCB/oxide samples suggests the inaccessibility of holes to undergo interfacial charge transfer with the organic substrate.