1-(4-methylbenzenesulfonyl)propan-2-one

• ChemBase ID: 37147
• Molecular Formular: C10H12O3S
• Molecular Mass: 212.26548
• Monoisotopic Mass: 212.05071524
• SMILES: S(=O)(=O)(CC(=O)C)c1ccc(cc1)C
• Canonical SMILES: CC(=O)CS(=O)(=O)c1ccc(cc1)C
• InChI: InChI=1S/C10H12O3S/c1-8-3-5-10(6-4-8)14(12,13)7-9(2)11/h3-6H,7H2,1-2H3
• InChIKey: NDQXJNHOGLQSMB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(4-methylbenzenesulfonyl)propan-2-one
• IUPAC Traditional name: 1-(4-methylbenzenesulfonyl)propan-2-one
• Synonyms: 1-[(4-methylbenzene)sulfonyl]propan-2-one; 1-[(4-Methylphenyl)sulfonyl]acetone; p-Toluenesulfonylacetone; 对甲苯磺酰丙酮

Database IDs

• CAS Number: 5366-49-4
• EC Number: 226-353-2
• MDL Number: MFCD00026240
• Beilstein Number: 1310695
• PubChem SID: 161000454
• PubChem CID: 79327

CALCULATED PROPERTIES

• Acid pKa: 10.702182
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 1.5911494
• LogD (pH = 7.4): 1.5909361
• Log P: 1.5911522
• Molar Refractivity: 54.4895 cm^3
• Polarizability: 21.841032 Å^3
• Polar Surface Area: 51.21 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 46 - 48°C; 52-55°C
• Hydrophobicity(logP): 0.852

Safety Information

• Storage Warning: IRRITANT
• TSCA Listed: false; 否

Product Information

• Purity: 95%; 98%

REFERENCES

• Readily forms the anion, even with weak base. After reaction with electrophiles, the arylsulfonyl group can be cleaved with sodium amalgam. For example, has been used as a 3-carbon unit for the extension of polyprenyl chains, to give the methyl ketone: Synthesis, 796 (1981):