bromotrimethylsilane

• ChemBase编号: 78793
• 分子式: C3H9BrSi
• 平均质量: 153.09306
• 单一同位素质量: 151.96568882
• SMILES: [Si](C)(C)(C)Br
• Canonical SMILES: C[Si](Br)(C)C
• InChI: InChI=1S/C3H9BrSi/c1-5(2,3)4/h1-3H3
• InChIKey: IYYIVELXUANFED-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: bromotrimethylsilane
• IUPAC传统名: bromotrimethylsilane
• 别名: 三甲基溴化硅; 三甲基溴硅烷; 溴三甲基硅烷; 三甲基溴硅烷; Trimethylsilyl bromide; TMBS; Bromotrimethylsilane; Trimethylbromosilane; Bromotrimethylsilane; TMS bromide

登记号

• CAS号: 2857-97-8
• EC号: 220-672-0
• MDL号: MFCD00000048
• Beilstein号: 1731135
• PubChem SID: 24851651; 162043556
• PubChem CID: 76113

理论计算性质

• 质子受体: 0
• 质子供体: 0
• LogD (pH = 5.5): 2.3134
• LogD (pH = 7.4): 2.3134
• Log P: 2.3134
• 摩尔折射率: 26.0755 cm^3
• 极化性: 11.969929 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

• 熔点: -44°C; -44°C
• 沸点: 78-80°C; 78-80°C; 79 °C(lit.)
• 闪点: 25 °C; 25°C; -3°C(26°F); 77 °F
• 密度: 1.16; 1.16 g/mL at 25 °C(lit.); 1.183
• 折射率: 1.424; 1.4250; n20/D 1.424; n20/D 1.424(lit.)

安全信息

• 保存注意事项: Corrosive/Flammable/Light Sensitive/Moisture Sensitive/Store under Argon/Keep Cold; Moisture 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: 2920; UN2924
• 德国WGK号: 3
• 联合国危险货物等级: 3; 8
• 联合国危险货物包装类别(PG): 2; II
• 危险公开号: 10-14-34; 11-14-34
• 安全公开号: 16-26-36/37/39-45
• TSCA收录: 是
• GHS危险品标识: GHS02; GHS05
• GHS警示词: Danger
• GHS危险声明: H225-H314-H318; H226-H314
• GHS警示性声明: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A; 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 2920 8/PG 2
• 欧盟补充危害声明: Reacts violently with water.
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥97.0% (AT); 97%; 97%, stab. with copper powder or silver wire
• 级别: purum
• 其他组分: copper as stabilizer; silver wool as stabilizer
• 线性分子式: (CH3)3SiBr

详细说明

Sigma Aldrich - 194409

Application
与 InCl3 共同用于催化用烯丙基三甲基硅烷直接烯丙基化各种醇。1
包装
25, 100 g in Sure/Seal™
5 g in glass bottle

Sigma Aldrich - 92337

Other Notes
强效甲硅烷基化试剂1,2；用于醚的裂解3；以及膦酸和磷酸烷基酯的平稳裂解4

参考文献

• Epoxides, oxetanes and THF are cleaved by the reagent: Synthesis, 383 (1981), as are small ring lactones: Angew. Chem. Int. Ed., 18, 689 (1979). The cleavage of acyclic ethers and esters is markedly catalyzed by IBr: J. Org. Chem., 48, 1678 (1983).
• In combination with DMSO and Et₃N, effects the bromolactonization of unsaturated acids: J. Chem. Soc., Perkin 1, 847 (1994).
• Effective catalyst for Michaelis-Arbuzov rearrangement of trivalent organophosphorus P-O-R compounds to the corresponding P=O derivatives: Org. Lett., 5, 1661 (2003).
• Compare also Iodotrimethylsilane, A12902.
• Converts alcohols to alkyl bromides: Tetrahedron Lett., 4483 (1978), and acyl chlorides to acyl bromides: Synthesis, 216 (1981).
• Silylating agent; see Appendix 4. About 10⁴x more reactive than TMSCl in the conversion of ketones to their silyl enol ethers in the presence of Et₃N: Liebigs Ann. Chem., 1718 (1980).
• Acetals, including MOM and THP ethers are readily cleaved, as are trityl and TBDMS ethers: Tetrahedron Lett., 25, 2515 (1984). Methyl glycosides are converted to the glycosyl bromides: Tetrahedron Lett., 22, 513 (1981).