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Thiophenol acts as a reagent to synthesize alfa, beta-unsaturated sulfides, beta-lactones and (3H-benzo[c][1,2]diselenol-3-yl)(phenyl)sulfane. It is used as an antinematodal agent and an intermediate in the preparation of sodium thiophenolate, pentachlorothiophenol and alkyl phenylsulfides. It acts as an inhibitor of human fibroblast collagenase in vitro.
For a detailed investigation of alkylation using, e.g. K2CO3 in acetone, see: Synth. Commun., 22, 1691 (1992). Unactivated aryl chlorides undergo nucleophilic substitution in the presence of K2CO3 in NMP to give aryl sulfides: J. Org. Chem., 56, 862 (1991).
Michael additions occur readily with electron deficient alkenes. Subsequent chlorination with NCS and dehydrochlorination provides a stereoselective route to vinyl thioethers: J. Org. Chem., 46, 235 (1981):
The Cu(I) derivative, phenylthiocopper forms complexes with alkyllithiums, which are useful alkyl transfer reagents, undergoing conjugate addition to enones, coupling with alkyl iodides to alkanes, and converting acid halides to ketones: J. Am. Chem. Soc., 95, 7788 (1973); Synthesis, 662 (1974); Org. Synth. Coll., 6, 248 (1988).
Chlorination of PhSH with NCS: J. Org. Chem., 37, 1367 (1972), or SO2Cl2: Org. Synth. Coll., 8, 550 (1993), gives the useful reagent benzenesulfenyl chloride, PhSCl.
Dilithiation of PhSH with n-BuLi and TMEDA gives exclusive ortho-metallation: J. Am. Chem. Soc., 111, 654, 665, 2327 (1989). Subsequent treatment of the dilithio species with DMF, followed by in situ reaction with chloroacetone provides a useful route to the benzo[b]thiophene system: J. Org. Chem., 58, 1293 (1993):
Interception of the DMF adduct provides a source of the unstable 2-mercaptobenzaldehyde. Alternatively, ortho-metallated thiophenols can be formed by lithiation of the THP ether, in which coordination by oxygen favors ortho-lithiation: J. Am. Chem. Soc., 111, 658 (1989).
Dhakshinamoorthy, A.; Primo, A.; Esteve-Adell, I.; Alvaro, M.; Garcia, H. Boron Nitride Nanoplatelets as a Solid Radical Initiator for the Aerobic Oxidation of Thiophenol to Diphenyldisulfide. ChemCatChem 2015, 7 (5), 776-780.
Reva, I.; Nowak, M. J.; Lapinski, L.; Fausto, R. Hydrogen atom transfer reactions in thiophenol: photogeneration of two new thione isomers. Phys. Chem. Chem. Phys. 2015, 17 (7), 4888-4898.
Hazard Statements: H226-H300+H310+H330-H315-H319-H335-H361-H371-H372
Flammable liquid and vapour. Fatal if swallowed. Fatal in contact with skin. Fatal if inhaled. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation. Suspected of damaging fertility or the unborn child. May cause damage to organs. Causes damage to organs through prolonged or repeated exposure.
Precautionary Statements: P201-P202-P210-P233-P235-P240-P241-P242-P243-P260-P262-P264b-P270-P271-P280i-P281-P284-P301+P310-P303+P361+P353-P304+P340-P305+P351+P338-P308+P313-P310-P330-P332+P313-P337+P31
Obtain special instructions before use. Do not handle until all safety precautions have been read and understood. Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep container tightly closed. Keep cool. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Use only non-sparking tools. Take precautionary measures against static discharge. Do not breathe dust/fume/gas/mist/vapours/spray. Do not get in eyes, on skin, or on clothing. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Wear eye/face protection. Use personal protective equipment as required. Wear respiratory protection. IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF exposed or concerned: Get medical advice/attention. Rinse mouth. If skin irritation occurs: If eye irritation persists: