ethyl 2-sulfanylacetate

• ChemBase ID: 78133
• Molecular Formular: C4H8O2S
• Molecular Mass: 120.17012
• Monoisotopic Mass: 120.0245005
• SMILES: O(C(=O)CS)CC
• Canonical SMILES: CCOC(=O)CS
• InChI: InChI=1S/C4H8O2S/c1-2-6-4(5)3-7/h7H,2-3H2,1H3
• InChIKey: PVBRSNZAOAJRKO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 2-sulfanylacetate
• IUPAC Traditional name: ethyl 2-sulfanylacetate
• Synonyms: Mercaptoacetic acid ethyl ester; Ethyl thioglycolate; ethyl 2-mercaptoacetate; Ethyl sulphanylacetate; Ethyl mercaptoacetate; Ethyl thioglycolate; Ethyl thioglycolate; Mercaptoacetic acid ethyl ester; Ethyl mercaptoacetate; 巯基乙酸乙酯; 硫代乙醇酸乙酯; 巯基乙酸乙酯

Database IDs

• CAS Number: 623-51-8
• EC Number: 210-800-3
• MDL Number: MFCD00004874
• Beilstein Number: 605581
• PubChem SID: 162042954; 24894515
• PubChem CID: 12185

CALCULATED PROPERTIES

• Acid pKa: 9.328021
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 0.5058618
• LogD (pH = 7.4): 0.50119454
• Log P: 0.5059217
• Molar Refractivity: 29.9906 cm^3
• Polarizability: 11.952434 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Colorless liquid
• Melting Point: -80°C
• Boiling Point: 156-159°C; 53-54°C/12mm; 54 °C/12 mmHg(lit.); 54°C
• Flash Point: 116.6 °F; 47 °C; 48°C; 48°C(118°F)
• Density: 1.096; 1.096 g/mL at 25 °C(lit.)
• Refractive Index: 1.4580; n20/D 1.457(lit.)

Safety Information

• Storage Warning: Air Sensitive; Toxic/Flammable
• RTECS: AI6650000
• European Hazard Symbols: Toxic (T)
• UN Number: 1228; 1992; UN1228
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 3; III
• Risk Statements: 10-25; 10-25-36/38
• Safety Statements: 23-36-45; 26-36/37/39-45
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H226-H301-H315-H319; H301-H226
• GHS Precautionary statements: P260-P280F-P233-P309-P310; P301 + P310-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1992 3/PG 3

Product Information

• Purity: 97%; 98+%; 99%
• Linear Formula: HSCH2COOC2H5

DETAILS

Sigma Aldrich - E34307

Packaging
5, 25 g in glass bottle

REFERENCES

• Reaction of the dilithio-derivative with an aldehyde, followed by conversion to the episulfide by reaction with ethyl chloroformate, and desulfurization with triethyl phosphite, leads to the (E)-2-alkenoic acid with high stereoselectivity: Synthesis, 127 (1983):