benzenethiol

• ChemBase ID: 75319
• Molecular Formular: C6H6S
• Molecular Mass: 110.17684
• Monoisotopic Mass: 110.01902119
• SMILES: Sc1ccccc1
• Canonical SMILES: Sc1ccccc1
• InChI: InChI=1S/C6H6S/c7-6-4-2-1-3-5-6/h1-5,7H
• InChIKey: RMVRSNDYEFQCLF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzenethiol
• IUPAC Traditional name: thiophenol
• Synonyms: Phenyl mecaptan; Benzenethiol; Thiophenol 99%; Thiophenol; Thiophenol; Phenyl mercaptan; Thiophenol; Benzenethiol; 硫酚; 巯基苯; 硫酚; 苯硫酚; 苯硫酚

Database IDs

• CAS Number: 108-98-5
• EC Number: 203-635-3
• MDL Number: MFCD00004826
• Beilstein Number: 506523
• Merck Index: 149355
• PubChem SID: 24900127; 24901811; 24854411; 162040237; 24846302
• PubChem CID: 7969
• CHEBI ID: 48498
• CHEMBL: 119405
• Chemspider ID: 7681
• FEMA ID: 3616
• Unique Ingredient Identifier: 7K011JR4T0
• Wikipedia Title: Thiophenol
• Council of Europe Number: 11585
• Flavis Number: 12.08

CALCULATED PROPERTIES

• Acid pKa: 6.638429
• H Acceptors: 0
• H Donor: 1
• LogD (pH = 5.5): 2.037154
• LogD (pH = 7.4): 1.320617
• Log P: 2.066453
• Molar Refractivity: 34.0678 cm^3
• Polarizability: 13.405632 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: colorless liquid, with unpleasant odour.
• Melting Point: -15 °C; -15 °C(lit.); -15°C; -15°C
• Boiling Point: 168-169°C; 169 °C; 169 °C(lit.); 169°C
• Flash Point: 122 °F; 50 °C; 55°C(131°F)
• Density: 1.073; 1.073 g/mL at 25 °C(lit.); 1.075; 1.0766 g/mL
• Refractive Index: 1.588; 1.5900; n20/D 1.588(lit.)
• Vapor Pressure: 1.4 mmHg ( 20 °C)
• Vapor Density: 3.8 (vs air)
• pKa: 8 (H₂O), 10 (DMSO)
• Organoleptic: alliaceous (onion, garlic)

Safety Information

• Storage Warning: Air Sensitive; Very Toxic/Flammable
• RTECS: DC0525000
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 2337; UN2337
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 1; I
• Risk Statements: 10-24/25-26-37/38-41-63; 10-24/25-26-41; R10 R24/25 R26 R41
• Safety Statements: 23-26-28-36/37/39-45; S23 S26 S28 S36/37/39 S45
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS05; GHS06; GHS08
• GHS Signal Word: Danger
• Main Hazard: Toxic
• GHS Hazard statements: H226-H300 +H310 + H330-H318; H300-H310-H330-H315-H335-H318-H226-H361
• GHS Precautionary statements: P260-P264-P280-P284-P301 + P310-P302 + P350; P260-P280-P305+P351+P338-P302+P352-P309-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2337 6.1/PG 1

Pharmacology Properties

• Allergens: no known allergens

Product Information

• Purity: ≥98%; ≥98.0% (GC); ≥99%; 97%; 99+%
• Grade: analytical standard; purum
• Shelf Life: (limited shelf life, expiry date on the label)
• Linear Formula: C6H5SH

DETAILS

Sigma Aldrich - T32808

Packaging
1 kg in Sure/Seal™
100, 500 g in Sure/Seal™

Sigma Aldrich - W361607

Packaging
1 kg in glass bottle
1 sample in glass bottle

Sigma Aldrich - 240249

Packaging
10 g in glass bottle
50 g in Sure/Seal™
Application
Used in the preparation of β-lactones.1
Protocols & Applications
The Progress in Development of Dental Restorative Materials

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).