methyl 2-(benzenesulfonyl)acetate

• ChemBase ID: 6450
• Molecular Formular: C9H10O4S
• Molecular Mass: 214.2383
• Monoisotopic Mass: 214.0299798
• SMILES: c1cccc(c1)S(=O)(=O)CC(=O)OC
• Canonical SMILES: COC(=O)CS(=O)(=O)c1ccccc1
• InChI: InChI=1S/C9H10O4S/c1-13-9(10)7-14(11,12)8-5-3-2-4-6-8/h2-6H,7H2,1H3
• InChIKey: NLEAIFBNKPYTGN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl 2-(benzenesulfonyl)acetate
• IUPAC Traditional name: methyl phenylsulfonyl acetate
• Synonyms: Methyl 2-(phenylsulfonyl)acetate; Methyl α-(phenylsulfonyl)acetate; Methyl benzenesulfonylacetate; Methyl phenylsulfonylacetate; METHYLPHENYLSULFONYLACETATE; Phenylsulfonylacetic acid methyl ester; 苯磺酰基乙酸甲酯; 苯磺酰乙酸甲酯

Database IDs

• CAS Number: 34097-60-4
• MDL Number: MFCD00007555
• Beilstein Number: 2051463
• PubChem SID: 24887415; 24854027; 160969757
• PubChem CID: 555619

CALCULATED PROPERTIES

• Acid pKa: 12.673295
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 0.89399934
• LogD (pH = 7.4): 0.8939971
• Log P: 0.8939994
• Molar Refractivity: 50.6663 cm^3
• Polarizability: 20.811878 Å^3
• Polar Surface Area: 60.44 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: ca 30°C
• Boiling Point: 165 °C/0.05 mmHg(lit.); 165°C/0.05mm; 165°C/0.05mm
• Flash Point: >110°C(230°F); 172.4 °F; 78 °C
• Density: 1.240; 1.282; 1.305 g/mL at 20 °C(lit.)
• Refractive Index: 1.5350; n20/D 1.535; n20/D 1.535(lit.)

Safety Information

• German water hazard class: 3
• TSCA Listed: false; 否
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter; Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)

Pharmacology Properties

• Gene Information: human ... LOC129293(129293)

Product Information

• Purity: ≥90% (GC); 97%; 98%
• Grade: technical
• Linear Formula: C6H5SO2CH2COOCH3

DETAILS

MP Biomedicals - 05216677

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 234184

Packaging
10 g in glass bottle

REFERENCES

• Active methylene compound used by Trost in Pd-catalyzed additions to allylic systems, providing, after desulfonation, methoxycarbonylmethyl derivatives under neutral conditions; see, e.g.: J. Am. Chem. Soc., 100, 3435 (1978); 103, 5969 (1981):
  
• See also: Tetrahedron Lett., 33, 1831 (1992). Desulfonation has been effected with Na amalgam: Tetrahedron Lett., 3477 (1976), Ca in liquid ammonia: J. Am. Chem. Soc., 100, 3435 (1978); or Mg in methanol: J. Org. Chem., 50, 1749 (1985).