608-93-5 Usage
Chemical Properties
Pentachlorobenzene is a colorless crystalline
solid. Pleasant aroma.
Uses
Different sources of media describe the Uses of 608-93-5 differently. You can refer to the following data:
1. It was used to prepare tetrachlorobenzene by photolysis.
2. Agrochemical researc
Definition
ChEBI: A member of the class of pentachlorobenzenes that is benzene in which five of the hydrogens are replaced by chlorines. Now classed as a persistent organic pollutant under the Stockholm Convention.
Synthesis Reference(s)
The Journal of Organic Chemistry, 38, p. 2928, 1973 DOI: 10.1021/jo00957a002
Air & Water Reactions
Insoluble in water.
Reactivity Profile
PENTACHLOROBENZENE is relatively unreactive. May be incompatible with strong oxidizing and reducing agents. Also may be incompatible with many amines, nitrides, azo/diazo compounds, alkali metals, and epoxides.
Fire Hazard
Flash point data for PENTACHLOROBENZENE are not available but PENTACHLOROBENZENE is probably non-flammable.
Safety Profile
Moderately toxic by ingestion. An experimental teratogen. When heated to decomposition it emits toxic fumes of Cl-. See also CHLORINATED HYDROCARBONS, AROMATIC
Potential Exposure
Pentachlorobenzene is used primarily
as a precursor in the synthesis of the fungicide pentachloronitrobenzene, and as a flame retardant. Drug/
Therapeutic Agent; Fungicide; bactericide; wood preservative;
industrial Insecticides.
Source
Pentachlorobenzene may enter the environment from leaking dielectric fluids containing
this compound. Pentachlorobenzene may be present as an undesirable by-product in the chemical
manufacture of hexachlorobenzene, pentachloronitrobenzene, tetrachloroenzenes, tetrachloroethylene,
trichloroethylene, and 1,2-dichloroethane (U.S. EPA, 1980).
Environmental Fate
Biological. In activated sludge, <0.1% mineralized to carbon dioxide after 5 days
(Freitag et al., 1985). From the first-order biotic and abiotic rate constants of pentachlorobenzene in estuarine water and sediment/water systems, the estimated biodegradation
half-lives were 4.6–6.5 and 6.0–7.6 days, respectively (Walker et al., 1988)Photolytic. UV irradiation (λ = 2537 ?) of pentachlorobenzene in a hexane solution
for 3 hours produced a 50% yield of 1,2,4,5-tetrachlorobenzene and a 13% yield of 1,2,3,5-
tetrachlorobenzene (Crosby and Hamadmad, 1971). Irradiation (λ ≥285 nm)A carbon dioxide yield of 2.0% was achieved when pentachlorobenzene adsorbed on
silica gel was irradiated with light (λ >290 nm) for 17 hours (Freitag et al., 1985).The experimental first-order decay rate for pentachlorobenzene in an aqueous solution
containing a nonionic surfactant micelle (Brij 58, a polyoxyethylene cetyl ether) and
illuminated by a photoreactor equipped with 253.7-nm monochromatic UV lamps, is 1.47
× 10–2/sec. The corresponding half-life is 47 seconds. Photoproducts reported include, alltetra-, tri- and dichlorobenzenes, chlorobenzene, benzene, phenol, hydrogen and chloride
ions (Chu and Jafvert, 1994)
Shipping
UN3077 Environmentally hazardous substances,
solid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous
hazardous material, Technical Name Required.
Incompatibilities
Polychlorinated hydrocarbons Incompatible
with oxidizers (chlorates, nitrates, peroxides, permanganates,
perchlorates, chlorine, bromine, fluorine, etc.);
contact may cause fires or explosions. Keep away from
alkaline materials, strong bases, strong acids, oxoacids,
epoxides, aluminum, liquid oxygen; potassium, sodium.
Waste Disposal
Consult with environmental
regulatory agencies for guidance on acceptable disposal
practices. Generators of waste containing this contaminant
(≥100 kg/mo) must conform with EPA regulations governing
storage, transportation, treatment, and waste disposal.
Incineration 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.
Check Digit Verification of cas no
The CAS Registry Mumber 608-93-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,0 and 8 respectively; the second part has 2 digits, 9 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 608-93:
(5*6)+(4*0)+(3*8)+(2*9)+(1*3)=75
75 % 10 = 5
So 608-93-5 is a valid CAS Registry Number.
608-93-5Relevant articles and documents
Electroreduction of hexachlorobenzene in micellar aqueous solutions of Triton-SP 175
Merica, Simona G.,Banceu, Claudia E.,Jedral, Wojciech,Lipkowski, Jacek,Bunce, Nigel J.
, p. 1509 - 1514 (1998)
The electrochemical reduction of hexachlorobenzene (HCB) has been studied in micellar aqueous solutions using Triton-SP 175 which, unlike conventional surfactants, is acid-labile. At pH 3, the hydrophobic residue cleaves from the hydrophilic chain, leaving a solution without surface- active properties and allowing recovery of the electrolysis products from the solution. A micellar solution containing 0.1% v/v Triton-SP 175 and 1% v/v heptane as cosolvent was indefinitely stable in the presence of 0.05 M sodium sulfate as an environmentally friendly supporting electrolyte. Electrolytic dehalogenation to less chlorinated benzenes was studied at a wide variety of cathodes; in all cases a quantitative material balance of phenyl residues was achieved. Lead was the preferred cathode in terms of both the degree of dechlorination achieved and the current efficiency. The electrochemical reduction of hexachlorobenzene (HCB) has been studied in micellar aqueous solutions using Triton-SP 175 which, unlike conventional surfactants, is acid-labile. At pH3, the hydrophobic residue cleaves from the hydrophilic chain, leaving a solution without surface-active properties and allowing recovery of the electrolysis products from the solution. A micellar solution containing 0.1% v/v Triton-SP 175 and 1% v/v heptane as cosolvent was indefinitely stable in the presence of 0.05 M sodium sulfate as an environmentally friendly supporting electrolyte. Electrolytic dehalogenation to less chlorinated benzenes was studied at a wide variety of cathodes; in all cases a quantitative material balance of phenyl residues was achieved. Lead was the preferred cathode in terms of both the degree of dechlorination achieved and the current efficiency.
Suzuki cross-coupling of hexachlorobenzene promoted by the Buchwald ligands
Burukin, A. S.,Vasil’ev, A. A.,Zhdankina, G. M.,Zlotin, S. G.
, p. 169 - 172 (2022/02/17)
The study of cross-coupling between hexachlorobenzene and phenylboronic acid comprised five Buchwald ligands, from which 2-dicyclohexylphosphino-2′-(dimethylamino)biphenyl (DavePHOS) provided the best conversion. When excess of phenylboronic acid was used, a mixture of isomeric tri-, tetra- and pentaphenyl-substituted derivatives in the ~10:70:20 ratio was obtained, along with minor amounts of hydrodechlorination products.
Frustrated Lewis pairs incorporating the bifunctional Lewis acid 1,1′-fc{B(C6F5)2}2: Reactivity towards small molecules
Tirfoin, Rémi,Gilbert, Jessica,Kelly, Michael J.,Aldridge, Simon
, p. 1588 - 1598 (2018/02/09)
Applications of the bifunctional ferrocenediyl Lewis acid 1,1′-fc{B(C6F5)2}2 in frustrated Lewis pair (FLP) chemistry are described. The coordination (or otherwise) of a range of sterically encumbered C-, N- and P-centred Lewis bases has been investigated, with lutidine, tetramethylpiperidine, PPh3, PtBu3 and the expanded ring carbene 6Dipp being found to be sterically incapable of coordinate bond formation. The chemistry of a range of these FLPs in the presence of H2O, NH3, CO2 and cyclohexylisocyanate (CyNCO) has been investigated, with the patterns of reactivity identified including simple coordination chemistry, E-H bond cleavage and C-B insertion.
Nickel-catalyzed hydrodehalogenation of aryl halides
Weidauer, Maik,Irran, Elisabeth,Someya, Chika I.,Haberberger, Michael,Enthaler, Stephan
supporting information, p. 53 - 59 (2013/08/25)
In the present study, the nickel-catalyzed dehalogenation of aryl and alkyl halides with iso-propyl zinc bromide or tert-butylmagnesium chloride has been examined in detail. With a straightforward nickel complex as pre-catalyst good to excellent yields and chemoselectivities were feasible for a variety of aryl and alkyl halides.