tris(propan-2-yl)silyl trifluoromethanesulfonate

• ChemBase编号: 148359
• 分子式: C10H21F3O3SSi
• 平均质量: 306.4176496
• 单一同位素质量: 306.09327672
• SMILES: CC(C)[Si](C(C)C)(C(C)C)OS(=O)(=O)C(F)(F)F
• Canonical SMILES: CC([Si](C(C)C)(C(C)C)OS(=O)(=O)C(F)(F)F)C
• InChI: InChI=1S/C10H21F3O3SSi/c1-7(2)18(8(3)4,9(5)6)16-17(14,15)10(11,12)13/h7-9H,1-6H3
• InChIKey: LHJCZOXMCGQVDQ-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: tris(propan-2-yl)silyl trifluoromethanesulfonate
• IUPAC传统名: triisopropylsilyl trifluoromethanesulfonate
• 别名: TIPS 三氟甲磺酸酯; 三异丙基甲硅烷基三氟甲磺酸酯; 三氟甲磺酸三异丙基硅基酯; 三异丙基硅基三氟甲磺酸酯; 三异丙基硅基三氟甲磺酸酯; 三异丙基甲硅烷基三氟甲烷磺酸盐; TIPS triflate; Trifluoromethanesulfonic acid triisopropylsilyl ester; Triisopropylsilyl triflate; Triisopropylsilyl trifluoromethanesulfonate; Wacker Silane IP3-triflate; TIPS-OTf; Triisopropylsilyl trifluoromethanesulfonate

登记号

• CAS号: 80522-42-5
• EC号: 000-000-0
• MDL号: MFCD00009913
• Beilstein号: 3591541
• PubChem SID: 24854929; 162242535; 24846002
• PubChem CID: 2724529

理论计算性质

• 质子受体: 2
• 质子供体: 0
• LogD (pH = 5.5): 5.1533
• LogD (pH = 7.4): 5.1533
• Log P: 5.1533
• 摩尔折射率: 60.4432 cm^3
• 极化性: 26.423628 Å^3
• 极化表面积: 43.37 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: false

分子性质

理化性质

• 沸点: 45-46 °C/0.03 mmHg; 45-46°C/0.03mm
• 闪点: 100°C(212°F); 103 °C; 217.4 °F
• 密度: 1.136; 1.14 g/mL at 25 °C(lit.)
• 折射率: 1.4150; n20/D 1.415(lit.)

安全信息

• 保存注意事项: Moisture Sensitive
• 欧盟危险性物质标志: 腐蚀性(Corrosive) (C)
• 联合国危险货物编号: 3265; UN3265
• 德国WGK号: 3
• 联合国危险货物等级: 8
• 联合国危险货物包装类别(PG): 2; II
• 危险公开号: 34
• 安全公开号: 26-36/37/39-45
• TSCA收录: 否
• GHS危险品标识: GHS05
• GHS警示词: Danger
• GHS危险声明: H314; H314-H318
• GHS警示性声明: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-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 3265 8/PG 2

产品相关信息

• 纯度: ≥98.0% (T); 95+%; 97%
• 级别: produced by Wacker; purum
• 线性分子式: CF3SO3Si[CH(CH3)2]3

详细说明

Sigma Aldrich - 248460

Application
用于由乙炔锂制备硅氧基乙炔；然后，可将硅氧基乙炔用于芳烃、炔烃和烯烃的质子酸促进的环化反应。1
包装
10, 50 g in glass bottle

Sigma Aldrich - 91746

Other Notes
用于顺利引入 TIPS 基团1,2,3,4；综述5

参考文献

• Reagent for introduction of the triisopropylsilyl (TIPS) group: Tetrahedron Lett., 22, 3455 (1981); compare Chlorotriisopropylsilane, A17376, and Appendix 4. For general reactions of silyl triflates, see Trimethylsilyl trifluoromethanesulfonate, A12535.
• For use in the synthesis of 2-substituted benzothiopyran-4-ones, see: Synlett, 182 (1996):
  
• A method for protecting both H atoms of a primary amine consists of formation of the succinimide, followed by enolsilylation with TIPS-OTf, to form the 2,5-bis(triisopropylsiloxy)pyrroles. Deprotection can be effected by desilylation with dilute HCl, followed by hydrazinolysis: Tetrahedron Lett., 38, 2617 (1997).
• For a comprehensive review of the TIPS group in organic chemistry, see: Chem. Rev., 95, 1009 (1995).