ethyl 2-methanesulfonylacetate

• ChemBase ID: 75419
• Molecular Formular: C5H10O4S
• Molecular Mass: 166.1955
• Monoisotopic Mass: 166.0299798
• SMILES: S(=O)(=O)(C)CC(=O)OCC
• Canonical SMILES: CCOC(=O)CS(=O)(=O)C
• InChI: InChI=1S/C5H10O4S/c1-3-9-5(6)4-10(2,7)8/h3-4H2,1-2H3
• InChIKey: OCCWQCYBCZADCE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 2-methanesulfonylacetate
• IUPAC Traditional name: ethyl 2-methanesulfonylacetate
• Synonyms: Ethyl 2-(methylsulphonyl)ethanoate; (Methylsulphonyl)acetic acid ethyl ester; Ethyl (methylsulphonyl)acetate 97%; Ethyl methylsulfonylacetate; Ethyl methanesulfonylacetate; Methylsulfonylacetic acid ethyl ester; 甲烷磺酰基乙酸乙酯

Database IDs

• CAS Number: 4455-15-6
• EC Number: 224-702-3
• MDL Number: MFCD00041258
• Beilstein Number: 1771631
• PubChem SID: 162040337; 24878398
• PubChem CID: 78201

CALCULATED PROPERTIES

• Acid pKa: 11.261992
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): -0.8637195
• LogD (pH = 7.4): -0.86377835
• Log P: -0.86371875
• Molar Refractivity: 35.8863 cm^3
• Polarizability: 15.026596 Å^3
• Polar Surface Area: 60.44 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 111-113 °C/0.2 mmHg(lit.); 111-113°C/0.2mm; 111-113°C/0.2mm
• Flash Point: >100°C(212°F); 109 °C; 109°C; 228.2 °F
• Density: 1.234; 1.234 g/mL at 25 °C(lit.); 1.260
• Refractive Index: 1.456; 1.4570; n20/D 1.456(lit.)

Safety Information

• Storage Warning: Irritant
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/38
• Safety Statements: 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Hazard statements: H315-H319
• GHS Precautionary statements: P280-P305+P351+P338-P302+P352-P321-P362-P332+P313
• Personal Protective Equipment: Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)

Product Information

• Purity: 97%
• Linear Formula: CH3SO2CH2COOC2H5

DETAILS

Sigma Aldrich - 539422

Packaging
5, 25, 100 g in glass bottle

REFERENCES

• Knoevenagel condensation occurs with aromatic aldehydes. Attempted hydrolysis with base results in reversal of the condensation reaction, but decarboethoxylation can be achieved by treatment with LiI in DMF, providing a useful synthesis of arylvinyl methyl sulfones: Synthesis, 806 (1980):