Pentachlorothiophenol

Grey solid

>300 °C closed cup

231.5 °C

Solid; [IUCLID] White to cream-colored solid with a disagreeable odor; [MSDSonline]

Stable under recommended storage conditions.

Warning

H319 (97.6%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

P264+P265, P280, P305+P351+P338, and P337+P317 (click each P-code to see the statement)

Aggregated GHS information provided per 42 reports by companies from 3 notifications to the ECHA C&L Inventory.；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Chemical: Benzenethiol, pentachloro-

Hazard Traits - Bioaccumulation; Environmental Persistence；Authoritative List - Canada PBiTs；Report - if used as a fragrance or flavor ingredient

R - indicates a substance that is the subject of a TSCA section 6 risk management rule.

Benzenethiol, pentachloro-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

A mild eye irritant; [RTECS] Emergency treatment: see Pentachlorophenol. [HSDB] A mild eye irritant, based on animal studies; [MSDSonline]

European Chemicals Bureau; IUCLID Dataset, Pentachlorobenzenethiol (133-49-3) contains information on use, toxicology, and environmental effects of this chemical as supplied to the European Union by industry.

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329. Effective date 8/27/01; Reporting date: 10/24/01.

Carbon oxides, Sulphur oxides, Hydrogen chloride gas

Eye Irrit. 2 (97.6%)

/Skin irritation/ after 24-hours exposure no irritation /in human/.

... slightly irritating to the respiratory tract

/Eye irritation/ Mild.

Strong oxidizing agents

Wear self contained breathing apparatus for fire fighting if necessary.

Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.

Keep container tightly closed in a dry and well-ventilated place.

ACCIDENTAL RELEASE MEASURES Personal precautions, protective equipment and emergency procedures Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Avoid breathing dust. For personal protection see section Environmental precautions Do not let product enter drains. Methods and materials for containment and cleaning up Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal.

SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a POTW is acceptable only after review by the governing authority. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must meet Hazardous Material Criteria for disposal.

SRP: Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.

Product: Offer surplus and non-recyclable solutions to a licensed disposal company. Contaminated packaging: Dispose of as unused product.

SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants. Ensure that the local ventilation moves the contaminant away from the worker.

Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.

Avoid contact with skin and eyes. Avoid formation of dust and aerosols.Further processing of solid materials may result in the formation of combustible dusts. The potential for combustible dust formation should be taken into consideration before additional processing occurs. Provide appropriate exhaust ventilation at places where dust is formed.

Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.

Skin protection Handle with gloves.

Eye/face protection Safety glasses with side-shields conforming to EN166 Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).

Respiratory protection: For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator. For higher level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).

Body Protection impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.

Pentachlorothiophenol is reported to be a metabolite of hexachlorobenzene in humans(1).

Pretreatment of rats with pentachlorophenol and pentachlorothiophenol (followed by hexachlorobenzene treatment) enhanced the turnover of two glutathione-binding substrates, 1,2-dichloro-n-nitrobenzene and 1,2-epoxy-3-(p-nitrophenoxy)propane.

LC100; Species: Brachydanio rerio (Zebrafish); Conditions: static bioassay; Concentration 2.8 mg/L for 96 hours

LC100; Species: Leuciscus idus (Golden orfe); Conditions: static bioassys; Concentration: 1.0 mg/L /test substance was/ 88% pentachlorothiophenol, 2% tetrachlorodithiol, pentachlorphenol, 10% Pentachlorbenzoldisulfide/

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 6,200(SRC), determined from a structure estimation method(2), indicates that pentachlorothiophenol is expected to be immobile in soil(SRC). Volatilization of pentachlorothiophenol from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.5X10-4 atm-cu m/mole(SRC), using a fragment constant estimation method(1). However, adsorption to soil is expected to attenuate volatilization(SRC). Pentachlorothiophenol is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 5.1X10-6 mm Hg(SRC), determined from a fragment constant method(2). A single biodegradation result noted 0% biodegradation of pentachlorothiophenol using a domestic sewage inoculum and a 30 incubation period(3).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 6,200(SRC), determined from a structure estimation method(2), indicates that pentachlorothiophenol is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 1.5X10-4 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). Using this Henry's Law constant and an estimation method(2), volatilization half-lives for a model river and model lake are 15 hours and 9.6 days, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The volatilization half-life from a model pond is about 150 days when adsorption is considered(4). According to a classification scheme(5), an estimated BCF of 3,700(SRC), from an estimated log Kow of 5.91(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is very high, provided the compound is not metabolized by the organism(SRC). A single biodegradation result noted 0% biodegradation of pentachlorothiophenol using a domestic sewage inoculum and a 30-day incubation period(6). Pentachlorothiophenol is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), pentachlorothiophenol, which has an estimated vapor pressure of 5.1X10-6 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase pentachlorothiophenol is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 115 days(SRC), calculated from its rate constant of 1.4X10-13 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(2). Particulate-phase pentachlorothiophenol may be removed from the air by wet or dry deposition(SRC). By analogy to pentachloro- and hexachlorobenzene which absorb at wavelengths >290 nm(3,4), pentachlorothiophenol may absorb at wavelengths >290 nm and be susceptible to direct photolysis by sunlight(SRC).

IDENTIFICATION AND USE: Pentachlorothiophenol (PCTP) was used as a peptizer for synthetic and natural rubbers. PTCP is replaced by 2,2'-dibenzamidodiphenyldisulfide (DBD) which is less toxic and reacts similarly. HUMAN EXPOSURE AND TOXICITY: PCTP did not produce skin irritation in human subjects after 24-hours exposure. ANIMAL STUDIES: Following inhalation exposure to 1 mg/L PCTP dust for 1 hr in both rats and rabbits, effects of the test substances were slightly irritating to the respiratory tract. The rabbits seemed to be more sensitive. Rats, a guinea pig, a rabbit and a cat were exposed to 2050 mg evaporated pentachlorothiophenol for 4 hours. Effects included: irritation of the mucous membranes in all animals (with the exception of the rats); at the following day the cat and rabbit still had conjunctivitis. PCTP did not produce any effects in dietary studies in rats. PCTP did not produced any developmental effects in chicken embryo. Salmonella typhimurium TA98, TA100, TA1535, and TA1537 test was negative with and without metabolic activation. PCTP acted as an uncoupler of oxidative phosphorylation in rat liver mitochondria. After administration of hexachlorobenzene rats excrete sulfur-containing conjugates from which PCTP can be split off.

Pentachlorothiophenol was detected as a metabolite of hexachlorobenzene in the roots of plants exposed to hexachlorobenzene(1).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of pentachlorothiophenol can be estimated to be 6,200(SRC). According to a classification scheme(2), this estimated Koc value suggests that pentachlorothiophenol is expected to be immobile in soil.

/HUMAN EXPOSURE STUDIES/ /Skin irritation/ after 24-hours exposure no irritation /in human/.

Pentachlorothiophenol has been detected in trout (Oncorhynchus sp) collected from Lake Michigan and Lake Superior(1).

Pentachlorothiophenol's former production and use as a peptizing agent for natural and synthetic rubber(1) may have resulted in its release to the environment through various waste streams(SRC). According to industry, no production, import or use of pentachlorobenzenethiol occurs at the present in the EU(2). Pentachlorothiophenol can be formed in the environment as a soil biotransformation metabolite of the fungicide quintozene (pentachloronitrobenzene)(3). Pentachlorothiophenol has also been identified as a plant and animal metabolite of both pentachloronitrobenzene and hexachlorobenzene(4,5).

AEROBIC: Pentachlorothiophenol biodegradation of 0% was reported using a domestic sewage inoculum and a 30-day incubation period(1). Biotransformation of pentachloronitrobenzene by four soil micromycetes yielded six metabolites including pentachlorothiophenol(2).

An estimated BCF of 3,700 was calculated in fish for pentachlorothiophenol(SRC), using an estimated log Kow of 5.91(1) and a regression-derived equation(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is very high, provided the compound is not metabolized by the organism(SRC).

Chemical: Benzenethiol, pentachloro-

Hazard Traits - Bioaccumulation; Environmental Persistence；Authoritative List - Canada PBiTs；Report - if used as a fragrance or flavor ingredient

R - indicates a substance that is the subject of a TSCA section 6 risk management rule.

Benzenethiol, pentachloro-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329. Effective date 8/27/01; Reporting date: 10/24/01.

Female rats were dosed intraperitoneally with 14C-hexachlorobenzene. The drug was administered on 2 or 3 occasions. The total doses amounted to 260 and 390 mg/kg 14C-hexachlorobenzene, respectively. Urine and feces from the animals were collected over a period of 4 wk after the first injection. Both excreta and some tissues of the animals were examined for their content of radioactivity and for hexachlorobenzene and its metabolites. ... In urine pentachlorophenol, tetrachlorohydroquinone, and pentachlorothiophenol were present as major metabolites. One of the isomers of tetrachlorothiophenol was present as a minor metabolite. In the feces pentachlorophenol and pentachlorothiophenol only were identified ...

After administration of hexachlorobenzene rats excrete sulfur-containing conjugates from which pentachlorothiophenol can be split off. The present study ... describe/s/ the identification of pentachlorothiophenol and pentachlorothioanisol in the livers of animals treated with hexachlorobenzene. In order to clarify the further fate of these two substances, /they were administered/ to rats, and ... the conversion products excreted in the urine and feces /were isolated/. The metabolites of pentachlorothiophenol and pentachlorothioanisol are excreted in both conjugated and free form. From extracts of the excreta, we isolated tetra- and trichlorobenzene with two or three sulfur-containing substituents on the ring, analogous compounds in which thiol groups were converted into sulphoxide and sulphone groups, as well as analogous compounds with a phenolic oxygen in addition to sulfur, and sulfur-containing compounds in which chlorine was replaced by hydrogen. Following administration of the sulfoxide and of the sulfone of pentachlorothioanisol under analogous conditions, pentachlorothiophenol and pentachlorothioanisol and their metabolites were detected in the excreta of the animals. No evidence was obtained that the parent compounds are excreted in the unchanged form.

The metabolism of pentachloronitrobenzene (PCNB) in rats was studied. Metabolites isolated from rat excreta and identified were: N-acetyl-S-(pentachlorophenyl)cysteine, pentachlorothiophenol, pentachlorothioanisole, 2,3,4,5-tetrachlorothiophenol, 2,3,4,5-tetrachlorothioanisole, 2,3,4,6- and/or 2,3,5,6-tetrachloro-thiophenol and -thioanisole, 1,4-bis(methylthio)tetrachlorobenzene, 1,4-dimercapto-tetrachlorobenzene and/or 4-methylthio-tetrachlorothiophenol, pentachlorophenol, pentachloroanisole, 2,3,4,5-tetrachlorophenol, 2,3,4,5-tetrachloroanisole, 2,3,4,6- and/or 2,3,5,6-tetrachloro-phenol and -anisole, pentachlorobenzene, 2,3,4,5-tetrachloronitrobenzene, pentachloroaniline and 2,3,4,5-tetrachloroaniline.

Male and female F 344 rats were dosed every other day for 103 days with 50 umole of hexachlorobenzene (HCB)/kg. ... Urine was periodically hydrolyzed and analyzed for the three metabolites pentachlorophenol, 2,3,5,6-tetrachlorobenzene-1,4-diol and pentachlorothiophenol (derived from the mercapturate). The combined urinary excretion of these was greater in females than males, especially during the first 10 weeks. Pentachlorothiophenol was particularly high in female urine. After 103 days this metabolite was slightly less in female feces than in male's but free hepatic pentachlorothiophenol was 3.6-fold greater. Although total 24 hr excretions of metabolites were higher by females than males and after 7 daily doses of HCB, a difference in this respect was not conclusively proven. However, total pentachlorothiophenol excretion was always significantly greater by females. The male/female ratios for pentachlorophenol and pentachlorothiophenol in bile were identical to those for feces. Excretion of metabolites by both adult males and females was stimulated by pretreatment with diethylstilbestrol (DES). No sex differences in metabolism were observed with immature rats.

For more Metabolism/Metabolites (Complete) data for PENTACHLOROTHIOPHENOL (21 total), please visit the HSDB record page.

Used as a peptizer for synthetic and natural rubbers; [HSDB]

... Mastication agent used in the rubber industry.

Peptizing agent for natural rubber viscosity reduction prior to blending with other polymers and/or filler incorporation

(1979) No Data

(1981) No Data

(1979) 7.76X10+8 g (Princpl Custms Dists)

(1981) 4.64X10+8 g (Princpl Custms Dists)

(1979) Not produced commercially in US.

(1981) Not produced commercially in US.

Production volumes for non-confidential chemicals reported under the Inventory Update Rule.[Table#5700]

Non-confidential 2012 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: Benzenethiol, 2,3,4,5,6-pentachloro-. National Production Volume: Withheld.

Pentachlorothiophenol is obtained from hexachlorobenzene by treatment with sodium sulfide and sulfur in methanol, or with sodium hydrogensulfide.

Reaction of hydrogen sulfide with pentachlorophenol in the presence of an acidic catalyst, eg, aluminum chloride or boron trifluoride

Benzenethiol, 2,3,4,5,6-pentachloro-: ACTIVE

For many years the preferred peptizer /for natural rubber/ was pentachlorothiophenol (PCTP) or its zinc salt ... PTCP is replaced by 2,2'-dibenzamidodiphenyldisulfide (DBD) which is less toxic and reacts similarly.

Processing agent - Natural rubber must be reduced in viscosity in order to obtain workable compounds. Many different chemical peptizers have been employed over the years for this purpose, including ... pentachlorothiophenol or its zinc salt ... The viscosity of natural rubber and synthetic polyisoprene can be reduced by mechanical shear alone, but using a peptizer makes the viscosity reduction during mixing less sensitive to variations in time and temperature, providing uniformity in viscosity from batch to batch.