trimethylsilanecarbonitrile

• ChemBase编号: 21464
• 分子式: C4H9NSi
• 平均质量: 99.20646
• 单一同位素质量: 99.05042583
• SMILES: C[Si](C)(C)C#N
• Canonical SMILES: N#C[Si](C)(C)C
• InChI: InChI=1S/C4H9NSi/c1-6(2,3)4-5/h1-3H3
• InChIKey: LEIMLDGFXIOXMT-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: trimethylsilanecarbonitrile
• IUPAC传统名: trimethylsilyl cyanide
• 别名: 氰化三甲基硅烷; 氰化三甲基硅烷; 三甲基氰硅烷; Trimethyl silane cyanide; Trimethylsilyl cyanide; Trimethylsilyl cyanide; Cyanotrimethylsilane; TMSCN; TMS cyanide; Trimethylsilylnitrile; Trimethylsilanecarbonitrile' Trimethylsilylcarbonitrile; TriMethylsilylcyanide

登记号

• CAS号: 7677-24-9
• EC号: 231-657-3
• MDL号: MFCD00001765
• Beilstein号: 1737612
• PubChem SID: 24886541; 24852746; 160984771; 24889714
• PubChem CID: 82115
• Chemspider ID: 74110
• 维基百科标题: Trimethylsilyl_cyanide

理论计算性质

• 质子受体: 1
• 质子供体: 0
• LogD (pH = 5.5): 1.9191
• LogD (pH = 7.4): 1.9191
• Log P: 1.9191
• 摩尔折射率: 23.3029 cm^3
• 极化性: 10.87245 Å^3
• 极化表面积: 23.79 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: organic solvents; reacts with water
• 外观: clorless liquid
• 熔点: 11-12°C; 11-12°C; 8 - 11°C; 8-11 °C(lit.)
• 沸点: 114 - 117°C; 114-117 °C(lit.); 118-119°C; 118-119°C
• 闪点: 1 °C; 1°C (33.8°F); 1.1°C; 1°C(33°F); 33.8 °F
• 密度: 0.744; 0.744 g/ml; 0.783; 0.793 g/mL at 20 °C; 0.793 g/mL at 20 °C(lit.)
• 折射率: 1.3910; 1.392; 1.3920; n20/D 1.391; n20/D 1.392(lit.)

安全信息

• 保存条件: Room Temperature (15-30°C), Desiccate
• 保存注意事项: KEEP COLD, TOXIC, FLAMMABLE; Moisture Sensitive
• 欧盟危险性物质标志: 易燃性(Flammable) (F); 环境危害性(Nature polluting) (N); 有毒(Toxic) (T); 剧毒(Highly toxic) (T+)
• 联合国危险货物编号: 2929; 3273; 3384; UN3383
• 德国WGK号: 3
• 联合国危险货物等级: 3; 6.1
• 联合国危险货物包装类别(PG): 1; I; II
• 澳大利亚Hazchem: 3WE
• 危险公开号: 11-26/27/28-29; 11-26/27/28-29-50/53; R:11-14-22; R11 R26/27/28 R29
• 安全公开号: 16-28-36/37/39-45-60-61; 16-36/37/39-45; S:8-9-16-29-30-45; S16 S36/37/39 S45
• 欧盟危险货物分类: TF1
• 欧盟危险识别号(EUHIN): 6.1A
• 美国ERG指导号: 131
• TSCA收录: false; 是
• GHS危险品标识: GHS02; GHS06; GHS09
• GHS警示词: Danger
• GHS危险声明: H225-H300 +H310 + H330; H225-H300-H310-H330-H400-H410
• GHS警示性声明: P210-P260-P264-P280-P284-P301 + P310; P210-P301+P310-P303+P361+P353-P304+P340-P320-P330-P361-P405-P501A
• 个人保护装置: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 3384 6.1/PG 1
• 欧盟补充危害声明: Contact with water liberates toxic gas.

产品相关信息

• 纯度: ≥95% (GC); ≥97.0% (H-NMR); 97%; 98%; 99%
• 级别: purum; technical
• 线性分子式: (CH3)3SiCN

详细说明

MP Biomedicals - 02105685

Purity: 98%
1 ml = approx. 0.74 g
Reagent for preparation of cyanohydrins.

Sigma Aldrich - 212849

Application
与醛和酮反应生成氰醇-TMS 醚，氰醇-TMS 醚可被还原为 β-氨基乙醇。
醛的氰基硅烷化反应试剂，反应由亚甲硅基桥联稀土氧化络合物催化，几乎有定量的产率。与手性双核钛(IV)络合物发生不对称的氰基硅烷化反应。
包装
25 g in Sure/Seal™
5 g in glass bottle

Sigma Aldrich - 73328

包装
50, 250 mL in glass bottle

Sigma Aldrich - 92755

Caution
储存时可能变为深黄色

参考文献

• Reagent for the formation of O-TMS cyanohydrins from carbonyl compounds.
• The ZnI₂-catalyzed procedure allows cyanohydrins of unreactive ketones to be prepared in good yield, avoiding the unfavourable equilibria often encountered with the classical alkali cyanide method. For details and list of examples, see: Org. Synth. Coll., 7, 20 (1990). Other catalysts including Et₃N or Bu₃P are also effective: Chem. Lett., 537, 541 (1991). For catalysis by Methyl triphenylphosphonium iodide, A15644, see: Tetrahedron Lett., 44, 6157 (2003). In the absence of a catalyst, aldehydes have been found to give good yields of the TMS cyanohydrin, but reaction with ketones is very slow: J. Chem. Soc., Perkin 1, 2383 (1995). For use of Tetracyanoethylene, A13945, as a c-acid catalyst for both aldehydes and ketones, see: J. Chem. Soc., Perkin 1, 2155 (1995). Under the same conditions, dimethyl acetals give O-methyl cyanohydrins.
• For examples of transformations of ketone TMS cyanohydrins, see: Chem. Pharm. Bull., 43, 1294 (1995).
• For use in asymmetric Strecker synthesis of chiral amino acids, see: Tetrahedron Lett., 29, 4397 (1988).
• Tertiary alkyl halides normally undergo elimination when treated with alkali cyanides, but can be converted to the corresponding nitriles by reaction with TMSCN in the presence of SnCl₄: Angew. Chem. Int. Ed., 20, 1017 (1981).
• Reacts with epoxides in the presence of ZnI₂ to give trans-ɑ-siloxy isocyanides, which can be readily hydrolyzed to the hydroxy isocyanides: J. Am. Chem. Soc., 104, 5849 (1982); Org. Synth. Coll., 7, 294 (1990). In the presence of Ag salts (AgClO₄, AgBF₄ or AgOTf), alkenes can be converted to isocyanides in Markovnikov fashion: Synlett, 288 (1999).
• For a brief survey of uses of this reagent in synthesis, see: Synlett, 1625 (2007).