N-(trimethylsilyl)acetamide

• ChemBase ID: 149045
• Molecular Formular: C5H13NOSi
• Molecular Mass: 131.24832
• Monoisotopic Mass: 131.07664057
• SMILES: CC(=O)N[Si](C)(C)C
• Canonical SMILES: CC(=O)N[Si](C)(C)C
• InChI: InChI=1S/C5H13NOSi/c1-5(7)6-8(2,3)4/h1-4H3,(H,6,7)
• InChIKey: LWFWUJCJKPUZLV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(trimethylsilyl)acetamide
• IUPAC Traditional name: acetamide, N-(trimethylsilyl)-
• Synonyms: N-Trimethylsilylacetamide; TMS acetamide; N-(Trimethylsilyl)acetamide; N-三甲基硅基乙酰胺; TMS 乙酰胺; N-(三甲基硅基)乙酰胺

Database IDs

• CAS Number: 13435-12-6
• EC Number: 236-565-7
• MDL Number: MFCD00008671
• Beilstein Number: 741928
• PubChem SID: 162243214; 24853373
• PubChem CID: 25989

CALCULATED PROPERTIES

• Acid pKa: 16.78503
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 0.6715998
• LogD (pH = 7.4): 0.6716
• Log P: 0.6716
• Molar Refractivity: 31.0062 cm^3
• Polarizability: 14.089556 Å^3
• Polar Surface Area: 29.1 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 38-43 °C; 39-43°C; 46-49 °C(lit.)
• Boiling Point: 104-106°C/35mm; 84 °C/18 mmHg(lit.)
• Flash Point: 70°C(158°F)

Safety Information

• Storage Warning: Moisture Sensitive
• RTECS: AD0250000
• European Hazard Symbols: Flammable (F); Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 11; 36/37/38
• Safety Statements: 26-37
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H228; H315-H319-H335
• GHS Precautionary statements: P210; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges

Product Information

• Purity: ≥90% (GC); 95%
• Grade: technical
• Linear Formula: CH3CONHSi(CH3)3

DETAILS

Sigma Aldrich - 223298

Packaging
25 g in glass bottle

Sigma Aldrich - 92745

Other Notes
Dianion formation and its alkylation and acylation1; Silylating agent of low reactivity2,3,4,5

REFERENCES

• Mild reagent for the silylation (see Appendix 4) of alcohols, including carbohydrates; cf N,O-Bis(trimethylsilyl)acetamide, L00183. O-Silylation in the presence of TBAB (0.02 equiv.) occurs under very mild conditions: Tetrahedron Lett., 35, 8409 (1994).
• Used in combination with triflic anhydride for N-glycosylation of sugars: J. Am. Chem. Soc., 111, 6881 (1989).
• n-BuLi forms the dilithio-derivative which can act as a soluble enolate equivalent of acetamide, reacting with electrophiles at carbon: J. Org. Chem., 49, 2015 (1984).