2-(methylsulfanyl)acetic acid

• ChemBase ID: 8506
• Molecular Formular: C3H6O2S
• Molecular Mass: 106.14354
• Monoisotopic Mass: 106.00885043
• SMILES: S(CC(=O)O)C
• Canonical SMILES: CSCC(=O)O
• InChI: InChI=1S/C3H6O2S/c1-6-2-3(4)5/h2H2,1H3,(H,4,5)
• InChIKey: HGTBAIVLETUVCG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(methylsulfanyl)acetic acid
• IUPAC Traditional name: (methylthio)acetic acid
• Synonyms: (Methylmercapto)acetic acid; (Methylthio)acetic acid; 2-(Methylthio)acetic acid 99%; (Methylthio)acetic acid; (甲基巯基)乙酸; (甲硫基)乙酸

Database IDs

• CAS Number: 2444-37-3
• EC Number: 219-483-6
• MDL Number: MFCD00075444
• Beilstein Number: 1740201
• PubChem SID: 160971813; 24862081
• PubChem CID: 75551

CALCULATED PROPERTIES

• Acid pKa: 4.3644753
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -0.7742243
• LogD (pH = 7.4): -2.5249019
• Log P: 0.39022893
• Molar Refractivity: 25.1239 cm^3
• Polarizability: 9.894117 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 13-14 °C(lit.); 13-14°C; 13-14°C
• Boiling Point: 130-131 °C/27 mmHg(lit.); 130-131°C/27mm; 130-137°C/27mm; 99-100°C/4mm
• Flash Point: >110°C; >110°C(230°F); 110 °C; 230 °F
• Density: 1.219; 1.219 g/mL at 25 °C(lit.); 1.224
• Refractive Index: 1.4950; n20/D 1.495; n20/D 1.495(lit.)

Safety Information

• Storage Warning: IRRITANT, STENCH; Irritant/Stench
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter

Product Information

• Purity: ≥98.5% (GC); 98%; 99%
• Grade: purum
• Linear Formula: CH3SCH2COOH

DETAILS

Sigma Aldrich - 359483

Packaging
5 mL in glass bottle

Sigma Aldrich - 69330

Other Notes
An acyl anion equivalent1; Review2

REFERENCES

• Dilithiation with LDA generates an acyl anion equivalent which, via alkylation and oxidative decarboxylation, provides a synthesis of aldehydes and ketones: Tetrahedron Lett., 3797 (1975).