2-(trimethylsilyl)acetic acid

• ChemBase ID: 147954
• Molecular Formular: C5H12O2Si
• Molecular Mass: 132.23308
• Monoisotopic Mass: 132.06065616
• SMILES: C[Si](C)(C)CC(=O)O
• Canonical SMILES: OC(=O)C[Si](C)(C)C
• InChI: InChI=1S/C5H12O2Si/c1-8(2,3)4-5(6)7/h4H2,1-3H3,(H,6,7)
• InChIKey: JDMMZVAKMAONFU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(trimethylsilyl)acetic acid
• IUPAC Traditional name: acetic acid, (trimethylsilyl)-
• Synonyms: (Trimethylsilyl)acetic acid; 三甲基硅基乙酸; (三甲基甲硅烷基)乙酸

Database IDs

• CAS Number: 2345-38-2
• EC Number: 219-067-4
• MDL Number: MFCD00042651
• Beilstein Number: 1679394
• PubChem SID: 24860972; 162242135
• PubChem CID: 75366

CALCULATED PROPERTIES

• Acid pKa: 4.571421
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 0.5150955
• LogD (pH = 7.4): -1.2808397
• Log P: 1.4913
• Molar Refractivity: 28.4286 cm^3
• Polarizability: 13.418272 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 39-42 °C; 39-42 °C(lit.); 40-42°C
• Boiling Point: 90-95°C/10mm
• Flash Point: 203 °F; 95 °C; 95°C(203°F)

Safety Information

• Storage Warning: Moisture Sensitive
• RTECS: AK0843500
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 2
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335; H315-H319-H335-H303
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥99.0% (T); 98+%; 99%
• Grade: purum
• Linear Formula: (CH3)3SiCH2CO2H

DETAILS

Sigma Aldrich - 341614

Packaging
1, 5 g in glass bottle

Sigma Aldrich - 92757

Other Notes
For the synthesis of α-trimethylsilylcarboxylic acids, α,β-unsaturated acids and α-trimethylsilyl-γ-butyrolactones via the dianion1; For the conversion of carbonyl compounds to α,β-unsaturated thiol esters2; Preparation of TMS-ketene3

REFERENCES

• The dilithiated derivative can undergo the Peterson olefination reaction (see Appendix 4), to give substituted acrylic acids, with alkyl halides to give alkyl silylacetic acids and with oxiranes to give -lactones: J. Chem. Soc., Chem. Commun., 537 (1975):
  
• Dehydration with DCC and Et₃N gives the ketene which is remarkably stable, showing little tendency to dimerize: Synthesis, 568 (1989).