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A15916 Thiophenol, 99+%

CAS Number
108-98-5
Synonyms
Benzenethiol
Phenyl mecaptan

Stock No. Size Price ($) Quantity Availability
A15916-09 10g 21.10
A15916-18 50g 25.80
A15916-30 250g 60.30
A15916-0B 1000g 177.00
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Thiophenol, 99+%

MDL
MFCD00004826
EINECS
203-635-3

Chemical Properties

Formula
C6H6S
Formula Weight
110.18
Melting point
-15°
Boiling Point
168-169°
Flash Point
55°(131°F)
Density
1.075
Refractive Index
1.5900
Storage & Sensitivity
Air Sensitive. Store under Nitrogen. Ambient temperatures.
Solubility
Miscible with most organic solvents and aqueous base. Immiscible with water.

Applications

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.

Notes

Incompatible with strong acids, bases and oxidizing agents.

Literature References

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.

GHS Hazard and Precautionary Statements

Hazard Statements: H226-H300-H310-H315-H319-H330-H335-H361-H371-H372

Flammable liquid and vapour. Fatal if swallowed. Fatal in contact with skin. Causes skin irritation. Causes serious eye irritation. Fatal if inhaled. 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:

Other References

Merck
14,9355
Beilstein
506523
Hazard Class
6.1
Packing Group
I
Harmonized Tariff Code
2930.90
TSCA
Yes
RTECS
DC0525000

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