N-(trimethylsilyl)acetamide

• ChemBase编号: 149045
• 分子式: C5H13NOSi
• 平均质量: 131.24832
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: N-(trimethylsilyl)acetamide
• IUPAC传统名: acetamide, N-(trimethylsilyl)-
• 别名: N-三甲基硅基乙酰胺; TMS 乙酰胺; N-(三甲基硅基)乙酰胺; N-Trimethylsilylacetamide; TMS acetamide; N-(Trimethylsilyl)acetamide

登记号

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

理论计算性质

• Acid pKa: 16.78503
• 质子受体: 1
• 质子供体: 1
• LogD (pH = 5.5): 0.6715998
• LogD (pH = 7.4): 0.6716
• Log P: 0.6716
• 摩尔折射率: 31.0062 cm^3
• 极化性: 14.089556 Å^3
• 极化表面积: 29.1 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

分子性质

理化性质

• 熔点: 38-43 °C; 39-43°C; 46-49 °C(lit.)
• 沸点: 104-106°C/35mm; 84 °C/18 mmHg(lit.)
• 闪点: 70°C(158°F)

安全信息

• 保存注意事项: Moisture Sensitive
• RTECS编号: AD0250000
• 欧盟危险性物质标志: 易燃性(Flammable) (F); 刺激性(Irritant) (Xi)
• 德国WGK号: 3
• 危险公开号: 11; 36/37/38
• 安全公开号: 26-37
• TSCA收录: 是
• GHS危险品标识: GHS02; GHS07
• GHS警示词: Warning
• GHS危险声明: H228; H315-H319-H335
• GHS警示性声明: P210; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• 个人保护装置: 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

产品相关信息

• 纯度: ≥90% (GC); 95%
• 级别: technical
• 线性分子式: CH3CONHSi(CH3)3

详细说明

Sigma Aldrich - 223298

包装
25 g in glass bottle

Sigma Aldrich - 92745

Other Notes
二价阴离子的形成及其烷基化和酰化反应1；低活性硅烷化试剂2,3,4,5

参考文献

• 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).