Trimethylsilyl trifluoromethanesulfonate 三甲硅烷基三氟甲磺酸酯

CAS 27607-77-8 MFCD00000406

化学结构图

27607-77-8
SMILES: C[Si](C)(C)OS(=O)(=O)C(F)(F)F

化学属性

Mol. FormulaC4H9F3O3SSi
Mol. Weight222.26
Refractive index1.3590 to 1.3610
Boiling Point77 °C at 80 mmHg
Density1.228 g/mL at 25 °C(lit.)
Flash Point25°C(lit.)
TSCAYes
Stability对湿度、空气敏感
SolubilitySoluble in water (react).
Melting Point25 °C

别名和识别编码

Chemical NameTrimethylsilyl trifluoromethanesulfonate
Synonym Trimethylsilyl trifluoromethylsulfonate {LY} Trimethylsilyl trifluoromethylsulfonate {} {LY} Trimethylsilyl trifluoromethylsulfonate {} {} {LY} Trimethylsilyl trifluoromethylsulfonate {} {} {} {LY} Trimethylsilyl trifluoromethylsulfonate {} {} {} {} {LY} Trimethylsilyl trifluoromethylsulfonate {} {} {} {} {} {LY} Trimethylsilyl trifluoromethylsulfonate {} {} {} {} {} {} {LY} Trimethylsilyl trifluoromethylsulfonate {} {} {} {} {} {} {} {LY} Trimethylsilyl trifluoromethylsulfonate {} {} {} {} {} {} {} {} {LY} Trimethylsilyl trifluoromethylsulfonate {} {} {} {} {} {} {} {} {} {LY} Trimethylsilyl trifluoromethylsulfonate {} {} {} {} {} {} {} {} {} {} {LY} Trimethylsilyl trifluoromethylsulfonate {} {} {} {} {} {} {} {} {} {} {} {LY} Trimethylsilyl trifluoromethylsulfonate {} {} {} {} {} {} {} {} {} {} {} {} {LY} Trimethylsilyl trifluoromethylsulfonate {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Trimethylsilyl trifluoromethylsulfon
PubChem Substance ID65367
EC Number248-565-4
Beilstein Registry Number1868911
MDL NumberMFCD00000406
CAS Number27607-77-8
Merck Number9719
Chemical Name Translation三甲硅烷基三氟甲磺酸酯
Reaxys-RN1868911
LabNetwork Molecule IDLN00194939
InChIInChI=1S/C4H9F3O3SSi/c1-12(2,3)10-11(8,9)4(5,6)7/h1-3H3
Canonical SMILESO=S(C(F)(F)F)(O[Si](C)(C)C)=O
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分类

  • {SNA} Chemical Synthesis, Protecting and Derivatizing Reagents, Protection and Derivatization, Silicon-Based, Synthetic Reagents
  • {uni_hamburg} no charge; 1fragment

产品应用

  • 常用于酯-酰亚胺和二酯的类 Dieckmann 环化试剂,也可用于制备强路易斯酸（特别是在乙腈溶剂中时）二氟硼三氟甲磺酸酯-乙醚络合物。

相关文献及参考

  • Merck: 14,9719
  • For a brief feature on uses of the reagent, see: Synlett, 1940 (2003).
  • In general, TMSOTf has a much greater tendency to give C-silylation than TMS chloride. With esters C-silylation usually predominates: Synthesis, 867 (1977); Liebigs Ann. Chem., 816 (1983). Nitriles are C-silylated: Synthesis, 636 (1977); Synth. Commun., 18, 2111 (1988). Electron-rich alkenes, e.g. ketene acetals, as well as electron-rich aromatics such as indoles and pyrroles also undergo C-silylation: Synthesis, 928, 929 (1984):
  • Trialkylsilyl perfluoroalkanesulfonates are highly reactive silylating agents (see Appendix 4) and Lewis acids: Synthesis, 1 (1982); Adv. Silicon Chem., 1, 189 (1991).
  • Short: EINECS
  • Short: III/35F
  • TMSOTf has numerous applications as a Lewis acid catalyst, notably in mediating, under very mild conditions, crossed aldol condensations between silyl enol ethers and acetals: J. Am. Chem. Soc., 102, 3248 (1980); Tetrahedron, 44, 4259 (1988); Org. Synth. Coll., 9, 642 (1998).
  • Amides can be N,O-disilylated with TMSOTf: Org. Synth. Coll., 9, 516 (1998). For conversion of carbonyl compounds to silyl enol ethers, see, e.g.: J. Org. Chem., 58, 1449 (1993); Org. Synth. Coll., 9, 548 (1998). The reaction rate in triethylamine is almost 109 times faster than with TMS chloride: Liebigs Ann. Chem., 1718 (1980).
  • tert-Butyl esters are cleaved directly to trimethylsilyl esters. Benzyl esters are unaffected, permitting selective cleavage: Synthesis, 545 (1980).

安全信息

GHS Symbol
WGK Germany3
Hazard statements
  • H226 Flammable liquid and vapour 易燃液体和蒸气
  • H314 Causes severe skin burns and eye damage 导致严重的皮肤灼伤和眼睛损伤
Personal Protective Equipment Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
Precautionary statements
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
  • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P305+P351+P338
  • P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防护手套/防护服/眼睛的保护物/面部保护物。
  • P260 Do not breathe dust/fume/gas/mist/vapours/spray. 不要吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P305+P351+P338+P310
  • P310 Immediately call a POISON CENTER or doctor/physician. 立即呼救解毒中心或医生/医师。
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • P301+P330+P331+P310
  • P303+P361+P353
  • P240 Ground/bond container and receiving equipment. 与地面接触/连接集装箱和接受设备。
  • P304+P340
  • P241 Use explosion-proof electrical/ventilating/lighting/…/equipment. 使用防爆电气/通风/照明/ .../设备。
  • P304+P340+P310
  • P403+P235
  • P210 Keep away from heat/sparks/open flames/hot surfaces. — No smoking. 远离热源/火花/明火/热的表面。——禁止吸烟。
  • P301+P330+P331
  • P241+P242+P243
  • P303+P361+P353+P310+P363
Signal word Danger Warning
Packing GroupII
UN Number 2920 UN2924
Risk Statements
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
  • R10 Flammable 易燃
  • R14 Reacts violently with water 遇水会猛烈反应
  • R34 Causes burns 会导致灼伤
Safety Statements
  • S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 眼睛接触后，立即用大量水冲洗并征求医生意见；
  • S36/37/39 Wear suitable protective clothing, gloves and eye/face protection 穿戴适当的防护服、手套和眼睛/面保护；
  • S45 In case of accident or if you feel unwell seek medical advice immediately (show the label where possible) 发生事故时或感觉不适时，立即求医（可能时出示标签）；
  • S16 Keep away from sources of ignition - No smoking 远离火源，禁止吸烟；
  • S30 Never add water to this product 切勿将水加入该产品中；
  • S20 When using do not eat or drink 使用时，不得进食，饮水；
  • S60 This material and its container must be disposed of as hazardous waste 该物质及其容器必须作为危险废物处置；
  • S8 Keep container dry 保持容器干燥；
Storage condition -20°C, sealed storage, away from moisture {LY} -20°C, sealed storage, away from moisture 2-8°C Moisture Sensitive {} {LY} -20°C, sealed storage, away from moisture {} {} {LY} -20°C, sealed storage, away from moisture {} {} {} {LY} -20°C, sealed storage, away from moisture {} {} {} {} {LY} -20°C, sealed storage, away from moisture {} {} {} {} {} {LY} -20°C, sealed storage, away from moisture {} {} {} {} {} {} {LY} -20°C, sealed storage, away from moisture {} {} {} {} {} {} {} {LY} -20°C, sealed storage, away from moisture {} {} {} {} {} {} {} {} {LY} -20°C, sealed storage, away from moisture {} {} {} {} {} {} {} {} {} {LY} -20°C, sealed storage, away from moisture {} {} {} {} {} {} {} {} {} {} {LY} -20°C, sealed storage, away from moisture {} {} {} {} {} {} {} {} {} {} {} {LY} -20°C, sealed storage, away from moisture {} {} {} {} {} {} {} {} {} {} {} {} {LY} -20°C, sealed storage, away from moisture {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} -20°C, sea
Hazard Codes C
Hazard Class8/3

其他信息

  • Trimethylsilyl trifluoromethanesulfonate is a strong Lewis acid catalyst and efficient silylating agent.
  • 和水反应。

系列性分类

  1. Chemical Synthesis 化学合成
  2. Synthetic Reagents 合成试剂
  3. Protection and Derivatization - Synthetic Reagents
  1. Analytical & Chromatography 分析化学与色谱
  2. Syringes
  3. GC Manual Syringes - Syringes
  4. Liquid sampling - GC Manual Syringes
  5. Syringe with sample in the needle, 0.5 - 5 µL - Liquid sampling
  6. Hamilton Modified Microliter™ Syringes, 7000 Series - Syringe with sample in the needle, 0.5 - 5 µL
  1. Chemical Synthesis 化学合成
  2. Synthetic Reagents 合成试剂
  3. Protection and Derivatization - Synthetic Reagents
  4. Protecting and Derivatizing Reagents - Protection and Derivatization
  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Chemicals by Class 化学分类法
  4. Halogenated 卤化物 (氟氯溴碘)
  5. Fluoro 氟化物
  1. Chemical Synthesis 化学合成
  2. Synthetic Reagents 合成试剂
  3. Protection and Derivatization - Synthetic Reagents
  4. Protecting and Derivatizing Reagents - Protection and Derivatization
  5. Silicon-Based - Protecting and Derivatizing Reagents
  1. Chemical Synthesis 化学合成
  2. Organometallic Reagents 金属有机试剂
  3. Organosilicon 有机硅
  4. Silanes 硅烷
  1. Chemical Synthesis 化学合成
  2. Synthetic Reagents 合成试剂
  3. Fluorous Chemistry 氟化学
  1. Chemical Synthesis 化学合成
  2. Synthetic Reagents 合成试剂
  3. Silicon Compounds for Organic Synthesis 硅化合物