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Thiophenol

Thiophenol Basic information
Product Name:Thiophenol
Synonyms:Thiophenol/Benzenethiol;THIOPHENOL;PHENYL MERCAPTAN;benzenethiolnylchloride;mercapto-benzen;Phenol, thio-;Phenylthiol;Rcra waste number P014
CAS:108-98-5
MF:C6H6S
MW:110.18
EINECS:203-635-3
Product Categories:Intermediates;Phenol&Thiophenol&Mercaptan;thiol Flavor;Building Blocks;Chemical Synthesis;Organic Building Blocks;Sulfur Compounds;Thiols/Mercaptans;Ring Thiols;Contact Printing;Materials Science;Micro/NanoElectronics;Self Assembly &;Self-Assembly Materials;Thiols
Mol File:108-98-5.mol
Thiophenol Structure
Thiophenol Chemical Properties
Melting point -15 °C
Boiling point 169 °C(lit.)
density 1.078
vapor density 3.8 (vs air)
vapor pressure 1.4 mm Hg ( 20 °C)
refractive index n20/D 1.588(lit.)
FEMA 3616 | BENZENETHIOL
Fp 123 °F
storage temp. Store at RT.
pka6.6(at 25℃)
form Liquid
color Clear colorless to slightly yellow
OdorUnpleasant
Water Solubility insoluble
Sensitive Stench
Merck 14,9355
JECFA Number525
BRN 506523
Exposure limitsTLV-TWA 0.5 ppm (~2.5 mg/m3 ) (ACGIH).
Stability:Stable. Flammable. May form explosive mixtures with air. Stench. Incompatible with strong oxidizing agents.
CAS DataBase Reference108-98-5(CAS DataBase Reference)
NIST Chemistry ReferenceBenzenethiol(108-98-5)
EPA Substance Registry SystemThiophenol (108-98-5)
Safety Information
Hazard Codes T+,T
Risk Statements 10-24/25-26-41-36/37/38
Safety Statements 23-26-28-36/37/39-45-28A-16
RIDADR UN 2337 6.1/PG 1
WGK Germany 3
RTECS DC0525000
10-13-23
Autoignition Temperature450 °C
Hazard Note Toxic/Stench
TSCA Yes
HazardClass 6.1
PackingGroup I
HS Code 29309099
Hazardous Substances Data108-98-5(Hazardous Substances Data)
MSDS Information
ProviderLanguage
SigmaAldrich English
ALFA English
Thiophenol Usage And Synthesis
Chemical Propertiescolorless liquid
Chemical PropertiesPhenyl mercaptan is a water white liquid. Repulsive, penetrating, rotten cabbage, garlic-like odor.
Chemical PropertiesBenzenethiol has a repulsive, penetrating, garlic-like odor.
OccurrenceReported found in cooked/boiled beef.
UsesIn the production of pesticides, polymers, and pharmaceuticals; as a food additive
UsesThiophenol is used as a mosquito larvicideand as an intermediate in organic synthesis.It is effective in reducing peroxide formationin jet fuels (Watkins et al. 1989).
UsesPharmaceutical synthesis.
PreparationBy reduction of benzenesulfonyl chloride with zinc dust in sulfuric acid.
DefinitionChEBI: A thiol in which the sulfanyl group is attached to a phenyl group.
Aroma threshold valuesDetection: 10 to 50 ppb
Synthesis Reference(s)Chemical and Pharmaceutical Bulletin, 35, p. 1770, 1987 DOI: 10.1248/cpb.35.1770
The Journal of Organic Chemistry, 16, p. 946, 1951 DOI: 10.1021/jo01146a019
Tetrahedron Letters, 21, p. 1677, 1980 DOI: 10.1016/S0040-4039(00)77784-7
General DescriptionA clear liquid with a repulsive odor. Boiling point 168.3°C. Insoluble in water and denser than water. Very toxic by ingestion, skin absorption, and by inhalation. Used as a chemical intermediate and in mosquito control.
Air & Water ReactionsFlammable. Oxidizes upon exposure to air, especially when dissolved in alcoholic ammonia, to form diphenyl disulfide, C6H5SSC6H5 [Merck 11th ed. 1989]. Is supplied under an atmosphere of nitrogen. Insoluble in water.
Reactivity ProfileThiophenol reacts with acids to generate toxic fumes of oxides of sulfur. [Lewis, 3rd ed., 1993, p. 1021]. Reacts exothermically with strong oxidizing agents.
HazardSkin irritant.
Health HazardMarked potential for causing eye changes. May cause death
Health HazardAnimal toxicity data show thiophenol to behighly toxic; the oral LD50 value in testanimals is <100 mg/kg. Its irritant actionon rabbits’ eyes and skin is severe. Thiophenol can enter the body by ingestion,absorption of the liquid through the skin,and inhalation of vapors. In humans, thetoxic symptoms include restlessness, incoordination, muscle weakness, headache, dizziness, cyanosis, lethargy, sedation, respiratorydepression, and coma. Death may result fromhigh doses. Repeated exposure to thiophenol vapors caused injury to the lung, liver,and kidneys in mice. Thiophenol did notadversely affect the growth, viability or morphological development of the offspring at adose of 40 mg/kg/day in rabbits (NTP 2005).
LC50 value, inhalation (mice): 28 ppm/4 h
LD50 value, oral (rats): 46 mg/kg
LD50 value, skin (rats): 300 mg/kg.
Fire HazardWhen heated to decomposition or on contact with acids, Thiophenol emits toxic fumes of sulfur oxides. May be ignited by heat, sparks or flames. Container may explode in heat of fire. Vapor explosion and poison hazard indoors, outdoors or in sewers. Unstable, oxidizes in air. Avoid contact with acids.
Safety ProfilePoison by ingestion, inhalation, skin contact, and intraperitoneal routes. A severe eye irritant. Can cause severe dermatitis. Exposure may cause headache and dminess. When heated to decomposition or on contact with acids it emits toxic fumes of SOx. See also MERCAPTANS
Potential ExposurePhenyl mercaptan is used as a chemical intermediate in pesticide manufacture; as a mosquito larvicide. It is used in solvent formulations for the removal of polysulfide sealants.
ShippingUN2337 Phenyl mercaptan, Hazard class: 6.1; Labels: 6.1-Poisonous materials, 3-Flammable liquid, Inhalation zone B.
IncompatibilitiesAt normal room temperature may vaporize forming explosive mixture with air. Violent reaction with strong 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, calcium hypochlorite, alkali metals. Oxidizes on exposure to air; supplied under nitrogen.
Waste DisposalConsult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (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. Dissolve in flammable solvent and burn in furnace equipped with afterburner and alkaline scrubber. 100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal. Dissolve in flammable solvent and burn in furnace equipped with afterburner and alkaline scrubber.
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