608-93-5

Basic information

• Product Name: PENTACHLOROBENZENE
• Synonyms: PENTACHLOROBENZENE;PENTACHLOROBENZENE 1000MG NEAT;PENTACHLOROBENZENE, 1X1ML, CH2CL2, 200UG /ML;PENTACHLORBENZOL PESTANAL;PENTACHLOROBENZENE 98+%;Benzene, pentachloro-;pentachlorobenzene solution;Pentachlorbenzol
• CAS NO: 608-93-5
• Molecular Formula: C₆HCl₅
• Molecular Weight: 250.34
• EINECS: 210-172-0
• Product Categories: Organics;Alphabetic;Alpha sort;N-PAlphabetic;P;PA - PEN;Pesticides&Metabolites;P-SAlphabetic;Volatiles/ Semivolatiles;Aryl;C6;Halogenated Hydrocarbons
• Mol File: 608-93-5.mol

Chemical Properties

• Melting Point: 84-87 °C(lit.)
• Boiling Point: 275-277 °C(lit.)
• Flash Point: 131.6°C
• Appearance: /
• Density: 1.609 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00783mmHg at 25°C
• Refractive Index: 1.5522 (estimate)
• Storage Temp.: 0-6°C
• Solubility: Very soluble in ether (Sax and Lewis, 1987)
• Water Solubility: 1.332mg/L(25 oC)
• BRN: 1911550
• CAS DataBase Reference: PENTACHLOROBENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: PENTACHLOROBENZENE(608-93-5)
• EPA Substance Registry System: PENTACHLOROBENZENE(608-93-5)

Safety Data

• Hazard Codes: F,Xn,N
• Statements: 11-22-50/53-40-67-36/37/38
• Safety Statements: 41-46-50-60-61-36/37-24/25-23
• RIDADR: UN 3077 9/PG 3
• WGK Germany: 3
• RTECS: DA6640000
• Hazardous Substances Data: 608-93-5(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
PENTACHLOROBENZENE is used as an intermediate in the preparation of tetrachlorobenzene through a process called photolysis. This application is significant in the chemical industry for the production of various compounds and materials.
Used in Agrochemical Research:
PENTACHLOROBENZENE is utilized in the field of agrochemical research, where it plays a role in the development and testing of new chemicals and compounds for agricultural purposes. Its properties make it a valuable component in the study and creation of effective and environmentally friendly agrochemicals.

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 PENTACHLOROBENZENE. 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.

Upstream product

• 56-23-5 tetrachloromethane 
• 69733-49-9 acetic acid-(2,3,5,6-tetrachloro-N-nitro-anilide) 
• 95-94-3 1,2,4,5-tetrachlorobenzene 
• 101654-40-4 1H,3H-hexachloro-hexa-1,3,5-triene 
• 18149-77-4 1H,6H-hexachloro-hexa-1,3,5-triene 
• 19635-52-0 2,3,4,5,6-pentachlorobenzaldehyde 
• 127-63-9 diphenyl sulphone 
• 13911-07-4 1,2,3,4-Tetrachloro-5-chloromethyl-benzene 
• 3481-20-7 2,3,5,6-tetrachloroaniline 
• 66063-39-6 2,3,5-trichloro-p-phenylenediamine 
• 13074-96-9 1-bromo-2,3,4,5,6-pentachlorobenzene 
• 19986-22-2 octachlorocyclohexane 
• 71-43-2 benzene 
• 67096-49-5 perchlorotriphenylsilane 

Downstream Products

• 98589-11-8 S-(2,3,5,6-tetrachloro-phenyl)-L-cysteine 
• 935-95-5 2,3,5,6-tetrachlorophenol 
• 4901-51-3 2,3,4,5-tetrachlorophenol 
• 82-68-8 Quintozene 
• 16478-18-5 2,3,4,5,6-pentachloroiodobenzene 
• 40707-29-7 pentachlorobenzenesulfonic acid 
• 39206-48-9 pentachlorobenzenesulfonic anhydride 
• 876498-70-3 4H-nonachloro-cyclohexene 
• 14260-47-0 dodecachloro-cyclohexane 
• 20276-25-9 2-[2-(2,3,4,5-tetrachloro-phenoxy)-ethoxy]-ethanol 
• 18713-24-1 Pentachlorphenyl-dimethylsilan 
• 33119-38-9 α-chlorobis(pentachlorophenyl)methane 
• 33240-61-8 αH-Pentadecachlorotriphenylmethane 
• 2136-95-0 pentachloro-α,α-dichlorotoluene 

Relevant articles and documents

Electroreduction of hexachlorobenzene in micellar aqueous solutions of Triton-SP 175

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.

Radiation induced catalytic dechlorination of hexachlorobenzene on oxide surfaces

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.

Synthesis of Decorated Carbon Structures with Encapsulated Components by Low-Voltage Electric Discharge Treatment

Abstract: Polycondensation of complexes of chloromethanes with triphenylphosphine by the action of low-voltage electric discharges in the liquid phase gives nanosized solid products. The elemental composition involving the generation of element distribution maps (scanning electron microscopy–energy dispersive X?ray spectroscopy mapping) and the component composition (by direct evolved gas analysis–mass spectrometry) of the solid products have been studied. The elemental and component compositions of the result-ing structures vary widely depending on the chlorine content in the substrate and on the amount of triphenylphosphine taken. Thermal desorption analysis revealed abnormal behavior of HCl and benzene present in the solid products. In thermal desorption spectra, these components appear at an uncharacteristically high temperature. The observed anomaly in the behavior of HCl is due to HCl binding into a complex of the solid anion HCI-2 with triphenyl(chloromethyl)phosphonium chloride, which requires a relatively high temperature (up to 800 K) to decompose. The abnormal behavior of benzene is associated with its encapsulated state in nanostructures. The appearance of benzene begins at 650 K and continues up to temperatures above 1300?K.

Suzuki cross-coupling of hexachlorobenzene promoted by the Buchwald ligands

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

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.

Dechlorination of hexachlorobenzene by nano zero-valent iron/activated carbon composite: Iron loading, kinetics and pathway

Nano zero-valent iron (nZVI) and activated carbon composites were synthesized and employed to remove hexachlorobenzene (HCB). Methods of impregnation and adsorption were employed to firstly load iron salt onto activated carbon, and thus loaded iron was then reduced to form zero valent iron. Results indicate that the method of iron loading significantly impacted the amount of iron and HCB dechlorination. In general, nZVI/activated carbon composite synthesized using an adsorption method showed considerably higher removal efficiency and dechlorination capability. More than 80% of the HCB was dechlorinated after 48 h. The dechlorination of HCB followed a stepwise pathway: HCB (hexachlorobenzene) → PCB (pentachlorobenzene) → 1,2,4,5 TeCB (tetrachlorobenzene) → TriCB (trichlorobenzene) → 1,4 DCB (dichlorobenzene) → MCB (monochlorobenzene). Compared with activated carbon or nZVI, nZVI/activated carbon composite showed much higher HCB removal. Analysis of mass partition on solid and aqueous phases indicates that most of the HCB and its dechlorination intermediates were retained on solids probably due to the strong adsorption on activated carbon. In summary, activated carbon performs three important functions: it alleviated the limitation of nZVI agglomeration, contributed to HCB removal due to its own adsorption capability and increased the resistance of nZVI against pH change. This journal is

Nickel-catalyzed hydrodehalogenation of aryl halides

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.

Selective C-F/C-H bond activation of fluoroarenes by cobalt complex supported with phosphine ligands

The reactions of pentafluoropyridine C5NF5, hexafluorobenzene C6F6, and perfluoronaphthalene C 10F8 with cobalt(0) complex, Co(PMe3) 4, were investigated. The Co(i) complexes (4-C5NF 4)Co(PMe3)3 (1), (C6F 5)Co(PMe3)3 (2), (C10F 7)Co(PMe3)3 (3), (4-C5NF 4)Co(PMe3)4 (4) and (C10F 7)Co(PMe3)4 (6) were obtained by selective activation of the C-F bonds. The reactions of 1 and 2 with CO afforded dicarbonyl cobalt(i) complexes (4-C5NF4)Co(CO) 2(PMe3)2 (7), (C6F 5)Co(CO)2(PMe3)2 (8). Under similar reaction conditions, 2 as a C-H bond activation product was obtained from the reaction of pentafluorobenzene, C6F5H, with Co(PMe 3)4. The byproducts, hydrodefluorination product 1,2,4,5-C6F4H2 and F2PMe3 from the reaction of C6F5H and Co(PMe3) 4 were also observed. The reaction mechanism of C6F 5H with Co(PMe3)4 is proposed and partly-experimentally verified. The reaction of C6F5H with Co(PMe3)4 under 1 bar of CO at room temperature afforded hydrido dicarbonyl cobalt(ii) complex (C6F5)Co(H)(CO) 2(PMe3)2 (11). Treatment of the mixtures of C6F5H/Co(PMe3)4 with hexachlorobenzene, C6Cl6, resulted in (C6F 5)CoCl(PMe3)3 (12) via C-H bond cleavage with the hydrodechlorination product pentachlorobenzene, C6Cl 5H, and 1,2,4,5-tetrachlorobenzene, C6Cl4H 2. The structures of complexes 1, 2, 6, 7, 8, 11 and 12 were determined by X-ray diffraction.

PROCESS FOR PRODUCING METHANOL

The present invention relates to a novel process for the production of methanol. The process comprises the heterolytic cleavage of hydrogen by a frustrated Lewis pair comprising a Lewis acid and a Lewis base; and the hydrogenation of CO2 with the heterolytically cleaved hydrogen to form methanol.

New look into the synthesis of polyhalogenoarylphosphanes

The present study shows new aspects of the synthesis of polyhalogenoarylphosphanes. The sterically hindered anions Ph(R)P-Y- (1a-c, Y = O, lone pair; R = Ph, But) have been used to show the complexity of the reaction between phosphorus nucleophiles and hexahalogenobenzenes or 9-bromofluorene (E3). The Ph(But)P-O-(1a) anion reacts with hexachlorobenzene (E1), hexafluorobenzene (E2), or E3 to give Ph(R)P(O)X (4a-c, X = F, Cl, Br) with the release of the corresponding carbanion as a nucleofuge, followed by side reactions. In contrast, the lithium phosphides Ph(R)PLi (1b,c) react with hexahalogenobenzenes to give the corresponding diphosphanes 5a,b as the main product and traces of P-arylated products, i.e., Ph(R)P-C6X 5 (10a,b, X = Cl, F). Unexpectedly, Ph(But)PLi (1b) reacts with an excess of 9-bromofluorene to give only halogenophosphane Ph(Bu t)P-X. Taylor & Francis Group, LLC.