methyl 2-(benzenesulfinyl)acetate

• ChemBase ID: 87011
• Molecular Formular: C9H10O3S
• Molecular Mass: 198.2389
• Monoisotopic Mass: 198.03506518
• SMILES: S(=O)(c1ccccc1)CC(=O)OC
• Canonical SMILES: COC(=O)CS(=O)c1ccccc1
• InChI: InChI=1S/C9H10O3S/c1-12-9(10)7-13(11)8-5-3-2-4-6-8/h2-6H,7H2,1H3
• InChIKey: JPPXZUDQIXZLIL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl 2-(benzenesulfinyl)acetate
• IUPAC Traditional name: methyl 2-(benzenesulfinyl)acetate
• Synonyms: methyl 2-(phenylsulphinyl)acetate; Methyl 2-phenylsulfinylacetate; 2-苯基亚磺酰基乙酸甲酯

Database IDs

• CAS Number: 14090-83-6
• EC Number: 237-936-6
• MDL Number: MFCD00002087
• Beilstein Number: 1953383
• PubChem SID: 162074127; 24854255
• PubChem CID: 84191

CALCULATED PROPERTIES

• Acid pKa: 13.920831
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.78710544
• LogD (pH = 7.4): 0.7871053
• Log P: 0.7871055
• Molar Refractivity: 51.1899 cm^3
• Polarizability: 20.230242 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 52-54 °C; 52-54 °C(lit.)
• Boiling Point: 130-131 °C/0.5 mmHg(lit.)
• Flash Point: 113 °C; 235.4 °F

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥97.0% (GC); 98%
• Grade: purum
• Linear Formula: C6H5S(O)CH2CO2CH3

DETAILS

Sigma Aldrich - 237582

Packaging
5 g in glass bottle
Application
Undergoes condensation reactions with aldehydes to form vinylic sulfoxides.1

Sigma Aldrich - 79175

Other Notes
Synthesis of enoates by alkylation / elimination1,2; 1,4-Addition to enoates3,4; Reaction with aldehydes5