methanesulfonylbenzene

• ChemBase ID: 7918
• Molecular Formular: C7H8O2S
• Molecular Mass: 156.20222
• Monoisotopic Mass: 156.0245005
• SMILES: CS(=O)(=O)c1ccccc1
• Canonical SMILES: CS(=O)(=O)c1ccccc1
• InChI: InChI=1S/C7H8O2S/c1-10(8,9)7-5-3-2-4-6-7/h2-6H,1H3
• InChIKey: JCDWETOKTFWTHA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methanesulfonylbenzene
• IUPAC Traditional name: sulfone, phenyl, methyl-
• Synonyms: Methyl phenyl sulfone; Methyl phenyl sulfone; (Methylsulphonyl)benzene; Methyl phenyl sulphone; 甲基苯基砜

Database IDs

• CAS Number: 3112-85-4
• EC Number: 221-476-8
• MDL Number: MFCD00014741
• Beilstein Number: 1906914
• PubChem SID: 160971225; 24885708
• PubChem CID: 18369

CALCULATED PROPERTIES

• Acid pKa: 19.698997
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.81355435
• LogD (pH = 7.4): 0.81355435
• Log P: 0.81355435
• Molar Refractivity: 40.0616 cm^3
• Polarizability: 16.307894 Å^3
• Polar Surface Area: 34.14 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 85-87 °C; 85-87°C; 85-88°C; 86-88°C

Safety Information

• Storage Warning: Harmful/Irritant
• RTECS: WR6800000
• European Hazard Symbols: X; Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• Safety Statements: 22-24/25; 36
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• GHS Precautionary statements: P264-P270-P301+P312-P330-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥98.0% (GC); 98%; 98+%
• Linear Formula: CH3SO2C6H5

DETAILS

Sigma Aldrich - 68742

Other Notes
Versatile building block for the construction of diverse functionalities1,2,3,4
Packaging
10 g in glass bottle

REFERENCES

• Factors governing the selective alkylation have been studied. Lithium bases favor dialkylation. For monoalkylation, a potassium base, e.g. KH in THF, should be used: J. Org. Chem., 55, 2234 (1990).
• Adds to aldehydes and ketones in the presence of base, e.g. n-BuLi, to give ?-hydroxy sulfones. Conversion of the OH to, e.g. to mesylate, and elimination/desulfurative reduction with sodium amalgam provides a 1-substitued or 1,1-disubstituted alkene by the Julia olefination reaction: Tetrahedron Lett., 4833 (1973); J. Chem. Soc., Perkin 1, 829 (1978). For reaction scheme, see Ethyl phenyl sulfone, A10710. The adducts with aldehydes can also be rearranged to give the dimethyl acetals of the homologous aldehydes: J. Chem. Soc., Perkin 1, 1646 (1978). Reaction with acyl halides gives ?-keto sulfones: J. Org. Chem., 53, 906 (1988).