iodotrimethylsilane

• ChemBase编号: 77997
• 分子式: C3H9ISi
• 平均质量: 200.09353
• 单一同位素质量: 199.95182482
• SMILES: [Si](C)(C)(C)I
• Canonical SMILES: C[Si](I)(C)C
• InChI: InChI=1S/C3H9ISi/c1-5(2,3)4/h1-3H3
• InChIKey: CSRZQMIRAZTJOY-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: iodotrimethylsilane
• IUPAC传统名: iodotrimethylsilane; trimethylsilyl iodide
• 别名: 碘代三甲硅烷; 三甲基碘硅烷; TMIS; Trimethyliodosilane; Iodotrimethylsilane; Iodotrimethylsilane; Trimethylsilyl iodide; TRIMETHYLIODOSILANE; Trimethylsilyl iodide; TMS iodide

登记号

• CAS号: 16029-98-4
• EC号: 240-171-0
• MDL号: MFCD00001028
• Beilstein号: 1731136
• PubChem SID: 24851696; 24881036; 162042833
• PubChem CID: 85247
• Chemspider ID: 76879
• 维基百科标题: Trimethylsilyl_iodide

理论计算性质

• 质子受体: 0
• 质子供体: 0
• LogD (pH = 5.5): 2.3119
• LogD (pH = 7.4): 2.3119
• Log P: 2.3119
• 摩尔折射率: 30.6811 cm^3
• 极化性: 14.281235 Å^3
• 极化表面积: 0.0 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

• 沸点: 105-106°C; 106 °C(lit.); 106°C/760mm
• 闪点: -2°C(28°F); -24 °F; -31 °C; -31°C
• 密度: 1.406 g/mL at 25 °C(lit.); 1.41 g/ml; 1.440
• 折射率: 1.4760; n20/D 1.471(lit.)

安全信息

• 保存条件: 0°C, Store Under Nitrogen
• 保存注意事项: Flammable/Corrosive/Hygroscopic/Store under Argon/Store at -20°C; Moisture & Light Sensitive
• 欧盟危险性物质标志: 腐蚀性(Corrosive) (C); 易燃性(Flammable) (F)
• 联合国危险货物编号: 2924; UN2924
• 德国WGK号: 3
• 联合国危险货物等级: 3
• 联合国危险货物包装类别(PG): 2; II
• 危险公开号: 11-14-34
• 安全公开号: 16-26-36/37/39-43.11-45; 16-26-36/37/39-43-45; 8-9-16-23-26-36/37/39-45-60
• TSCA收录: 是
• GHS危险品标识: GHS02; GHS05
• GHS警示词: Danger
• GHS危险声明: H225-H314; H225-H314-H318
• GHS警示性声明: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A; P210-P280-P305 + P351 + P338-P310
• 个人保护装置: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2924 3/PG 2
• 欧盟补充危害声明: Reacts violently with water.
• 保存温度: -20°C

产品相关信息

• 纯度: ≥90%; ≥98.0% (AT); 97%; 97%, stab. with copper
• 级别: purum
• 其他组分: ~1% copper as stabilizer; copper as stabilizer
• 运输包装: wet ice
• 线性分子式: (CH3)3SiI

详细说明

MP Biomedicals - 02157076

Purity: >90%
Stabilized with copper
1 ml = approx. 1.41 g

Sigma Aldrich - 195529

Application
最近报道用于将烯丙基以及苄基磷酸三酯转化为相应的碘化物的试剂。
用于引入 TMS 基团，如 TMS 烯醇醚。用于在三甲基锡基存在的条件下对 N-Cbz 基团进行选择性脱保护的重要试剂。
用于裂解醚、酯、氨基甲酸盐、缩酮和内酯的有效试剂。1
包装
5, 25, 100 g in ampule

Sigma Aldrich - 58118

Other Notes
通用试剂。例如用于裂解醚、酯、氨基甲酸盐以及缩酮，也用于亚砜的脱氧作用，或用于碘化物的合成等。综述1,2,3；强效硅烷化试剂4,5

参考文献

• Valuable reagent for the mild cleavage of dialkyl and aralkyl ethers: J. Org. Chem., 42, 3761 (1977).
• Catalyzes the transesterification of esters, even those of hindered acids: Synthesis, 142 (1981).
• Reactive silylating agent for conversion of ketones to silyl enol ethers (see Appendix 4). In triethylamine, the rate of silyl enol ether formation by TMS iodide is 7x10⁹ times faster than with TMS chloride: Liebigs Ann. Chem., 1718 (1980). In combination with Hexamethyldisilazane, A15139, unsymmetrical ketones give the thermodynamically more stable isomer: Synthesis, 730 (1979).
• Alcohols are converted to alkyl iodides: Tetrahedron Lett., 2659 (1977). ɑɑ-Diaryl alcohols are reduced to the corresponding alkanes: Tetrahedron, 51, 11043 (1995); Synth. Commun., 26, 101 (1996).
• Effective reagent for the O-alkyl cleavage of carboxylic esters: J. Am. Chem. Soc., 99, 968 (1977). The reaction can be catalyzed by iodine: J. Org. Chem., 44, 2185 (1979).
• Alkyl carbamates are cleaved to amines, via the TMS esters: J. Chem. Soc., Chem. Commun., 315 (1978); for application to cleavage of N-Cbz and N-Boc groups, see: J. Chem. Soc., Chem. Commun., 495 (1979).
• Catalyst for the protection of alcohols, under mild neutral conditions, as MOM ethers by trans-acetalization with Dimethoxymethane, A12055: Synthesis, 896 (1983), and as THP ethers by acetalization with dihydropyran: Synthesis, 703 (1985).
• Catalyst for Michaelis-Arbuzov rearrangement of trivalent organophosphorus P-O-R compounds to the corresponding P=O derivatives, effective at lower temperatures than bromotrimethylsilane: Org. Lett., 5, 1661 (2003).
• For reviews of the use of iodotrimethylsilane in organic synthesis, see: Synthesis, 861 (1980); Tetrahedron, 38, 2225 (1982); Adv. Silicon Chem., 1, 1 (1991).