2-(4-methylbenzenesulfonyl)ethan-1-ol

• ChemBase ID: 149431
• Molecular Formular: C9H12O3S
• Molecular Mass: 200.25478
• Monoisotopic Mass: 200.05071524
• SMILES: Cc1ccc(cc1)S(=O)(=O)CCO
• Canonical SMILES: OCCS(=O)(=O)c1ccc(cc1)C
• InChI: InChI=1S/C9H12O3S/c1-8-2-4-9(5-3-8)13(11,12)7-6-10/h2-5,10H,6-7H2,1H3
• InChIKey: QJFIXBNLKARINT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(4-methylbenzenesulfonyl)ethan-1-ol
• IUPAC Traditional name: 2-(4-methylbenzenesulfonyl)ethanol
• Synonyms: MPSE; 2-(p-Tolylsulfonyl)ethanol; 2-Hydroxyethyl 4-methylphenyl sulfone; 2-(4-Methylphenylsulfonyl)ethanol; 2-(p-Tolylsulfonyl)ethanol; 2-(4-Methylphenylsulfonyl)ethanol; 2-(p-Tosyl)ethanol; 2-(p-Toluenesulfonyl)ethanol; 2-(对甲苯磺酰)乙醇; 2-羟乙基 4-甲基苯基砜; 2-(4-甲苯磺酰)乙醇; 2-(对甲苯磺酰)乙醇

Database IDs

• CAS Number: 22381-54-0
• EC Number: 000-000-0
• MDL Number: MFCD00041757
• Beilstein Number: 1961132
• PubChem SID: 24889017; 162243596; 24868272
• PubChem CID: 89682

CALCULATED PROPERTIES

• Acid pKa: 14.883533
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 0.789063
• LogD (pH = 7.4): 0.7890629
• Log P: 0.789063
• Molar Refractivity: 50.8985 cm^3
• Polarizability: 20.549145 Å^3
• Polar Surface Area: 54.37 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 50-53°C; 50-56 °C(lit.); 52-57 °C
• Boiling Point: 178-181 °C/0.2 mmHg(lit.); 178-181°C/0.2mm

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302

Product Information

• Purity: ≥96.0% (GC); 97%; 98%
• Grade: purum
• Linear Formula: CH3C6H4SO2CH2CH2OH
• Empirical Formula (Hill Notation): C9H12O3S

DETAILS

Sigma Aldrich - 446386

Packaging
10 g in glass bottle

REFERENCES

• Reagent for protection of the carboxyl group as its 2-(p-toluenesulfonyl)ethyl (Tse) [2-(4-methylphenylsulfonyl)ethyl (Mpse)] ester, e.g. by DCC coupling. The Tse group is useful for carboxyl protection of Boc amino acids in peptide synthesis, since it is stable to the acidic conditions used for Boc cleavage, but readily cleaved by mild base, e.g. dilute NaOH or Na₂CO₃ in dioxan-water: J. Chem. Soc.(C)., 2612 (1968). It can also be cleaved by non-aqueous bases, e.g. DBN: J. Chem. Soc., Chem. Commun., 1031 (1972), DBU: Tetrahedron Lett., 25, 2163 (1984), or TBAF in THF: Chem. Lett., 1595 (1987).