Pentachlorothiophenol

282.384

282.40

204-224-1

92A1Z48VJB

5578

DTXSID3044540

Grey solid

29309090

1

5.91 (est)

Off-white to White Powder

1.693 (estimate)

240 °C

351.3±37.0 °C(Predicted)

>300 deg C closed cup

1.648

In water, 4.8X10-3 mg/L at 25 deg C (est)

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

5.1X10-6 mm Hg at 25 deg C (est)

LD50 orl-rat: 11,900 g/kg 28ZPAK -,168,72

Henry's Law constant = 1.5X10-4 atm-cu m/mol at 25 °C (est)

Hydroxyl radical reaction rate constant = 1.4X10-13 cu cm/molec-sec at 25 °C (est)

UN 3335

3

R20/22

26

DC1925000

Stable under recommended storage conditions.

P305 + P351 + P338

H319

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.

Strong oxidizing agents

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.

|Warning|H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]|P264, P280, P305+P351+P338, and P337+P313|Aggregated GHS information provided by 41 companies from 2 notifications to the ECHA C&L Inventory.|Danger|H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]|P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P405, and P501|Aggregated GHS information provided by 38 companies from 1 notifications to the ECHA C&L Inventory.

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.

Wear self contained breathing apparatus for fire fighting if necessary.|Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.

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: 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 irritation/ after 24-hours exposure no irritation /in human/.|... slightly irritating to the respiratory tract|/Eye irritation/ Mild.

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.

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.

LD50 Rat oral 11,900 mg/kg|LD50 Mouse oral 1,000-4,000 mg/kg|LD50 Mouse ip 100-200 mg/kg|LD50 Mouse ip 280 mg/kg bw

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).

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).

The rate constant for the vapor-phase reaction of pentachlorothiophenol with photochemically-produced hydroxyl radicals has been estimated as 1.4X10-13 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 115 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Pentachlorothiophenol is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). Pentachlorobenzene absorbs UV light >290 nm(3) and hexachlorobenzene absorbs UV light >290 nm and has been shown to photodegrade in water-acetonitrile solution when exposed to light >290 nm(4). By analogy, pentachlorothiophenol may absorb at wavelengths >290 nm and be susceptible to direct photolysis by sunlight(SRC).

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).

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.

The Henry's Law constant for pentachlorothiophenol is estimated as 1.5X10-4 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that pentachlorothiophenol is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 15 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 9.6 days(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(3). Pentachlorothiophenol's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(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(1).

According to the 2012 TSCA Inventory Update Reporting data, 1 reporting facility estimates the number of persons reasonably likely to be exposed during the manufacturing, processing, or use of pentachlorothiophenol in the United States may be as low as 25-49 workers and as high as 25-49 workers per plant; the data may be greatly underestimated due to confidential business information (CBI) or unknown values(1).|NIOSH (NOES Survey 1981-1983) has statistically estimated that 24,076 workers (2,595 of these were female) were potentially exposed to pentachlorothiophenol in the US(1). Occupational exposure to pentachlorothiophenol may occur through dermal contact with this compound at workplaces where pentachlorothiophenol is produced or use(SRC). Monitoring data indicate that the general population may be exposed to pentachlorothiophenol via ingestion of fish, animals or plants containing pentachlorothiophenol as a metabolite of the fungicide quintozene or hexachlorobenzene(SRC). Pentachlorothiophenol is reported to be a metabolite of hexachlorobenzene in humans(2).

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

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.

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Pentachlorophenol and Related Compounds/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for shock and treat if necessary ... . Monitor for pulmonary edema and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . Cover skin burns with dry sterile dressings after decontamination ... . Rapid body cooling may be necessary in case of hyperthermia. Use of salicylates is contraindicated. /Pentachlorophenol and Related Compounds/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start IV administration of 0.9% saline (NS) or lactated Ringer's (LR) /SRP: "To keep open", minimal flow rate/. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload, cerebral edema, and pulmonary edema ... .Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Pentachlorophenol and Related Compounds/

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

pentachlorothiophenol

Benzenethiol, 2,3,4,5,6-pentachloro-, zinc salt (2:1): ACTIVE|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.