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Trimethylsilyl trifluoromethanesulfonate 三氟甲磺酸三甲基硅酯

规格: 99%

CAS: 27607-77-8

产品编号: H86908

MDL: MFCD00000406

品牌: INFI

Chemical Name	Trimethylsilyl trifluoromethanesulfonate
Synonym	Trimethylsilyl trifluoromethylsulfonate
PubChem Substance ID	65367
EC Number	248-565-4
Beilstein Registry Number	1868911
MDL Number	MFCD00000406
CAS Number	27607-77-8
Merck Number	9719
Chemical Name Translation	三氟甲磺酸三甲基硅酯
Reaxys-RN	1868911
LabNetwork Molecule ID	LN00194939
InChI	InChI=1S/C4H9F3O3SSi/c1-12(2,3)10-11(8,9)4(5,6)7/h1-3H3
Canonical SMILES	O=S(C(F)(F)F)(O[Si](C)(C)C)=O

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。

{ALD} Merck: 14,9719

{ALF} For a brief feature on uses of the reagent, see: Synlett, 1940 (2003).

{ALF} 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):

{ALF} Trialkylsilyl perfluoroalkanesulfonates are highly reactive silylating agents (see Appendix 4) and Lewis acids: Synthesis, 1 (1982); Adv. Silicon Chem., 1, 189 (1991).

{uni_hamburg} Short: EINECS

{uni_hamburg} Short: III/35F

{ALF} 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).

{ALF} 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).

{ALF} tert-Butyl esters are cleaved directly to trimethylsilyl esters. Benzyl esters are unaffected, permitting selective cleavage: Synthesis, 545 (1980).

27607-77-8 H86908 Trimethylsilyl trifluoromethanesulfonate
三氟甲磺酸三甲基硅酯

化学属性

Mol. Formula	C4H9F3O3SSi
Mol. Weight	222.26
Refractive index	1.3590 to 1.3610
Boiling Point	77 °C at 80 mmHg
Density	1.228
Flash Point	25°C
TSCA	Yes
Stability	对湿度、空气敏感
Solubility	Soluble in water (react).
Melting Point	25 °C

*以上化合物性质及应用等信息仅供参考

电子化学品

催化剂

配体

有机硅

元素分类

其他精细新材料

Trimethylsilyl trifluoromethanesulfonate 三氟甲磺酸三甲基硅酯

规格: 99%

化学属性

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