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一般說明
Trimethyl(trifluoromethyl)silane (TMSCF3) is also called as Ruppert-Prakash fluorination reagent. It is extensively used for the synthesis of trifluoromethyl-containing compounds.
應用
Reactant for:
- Silver-mediated C-H trifluoromethylation of arenes
- Preparation of trifluoromethyl ketone analog of L-arginine having contrasting inhibitory activity against human arginase I and histone deacetylase 8
- Organocatalyzed regio- and enantioselective allylic trifluoromethylation of Morita-Baylis-Hillman adducts
- Palladium-catalyzed oxidative trifluoromethylation of indoles
- Preparation of 5-HT1A antagonists
- Used as difluorocarbene source
TMSCF3 can be used as a reagent for:
It can also be used in trifluoromethylation of:
- Conversion of aromatic aldehydes to difluoromethylated products.
- C-H trifluoromethylation of arenes, terminal alkynes, tertiary amines, heteroarenes, allylic, and terminal alkenes using metal catalyst or metal free oxidative trifluoromethylation reaction.
It can also be used in trifluoromethylation of:
- Non-activated aldimines.
- Heterocumulenes.
- Azomethine imines.
訊號詞
Danger
危險分類
Acute Tox. 4 Oral - Carc. 2 - Eye Irrit. 2 - Flam. Liq. 2 - STOT SE 3
標靶器官
Respiratory system
安全危害
儲存類別代碼
3 - Flammable liquids
水污染物質分類(WGK)
WGK 3
閃點(°F)
1.4 °F
閃點(°C)
-17 °C
個人防護裝備
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Organocatalyzed Regio-and Enantioselective Allylic Trifluoromethylation of Morita-Baylis-Hillman Adducts Using Ruppert-Prakash Reagent
Organic Letters, 13(15), 3972-3975 (2011)
Nucleophilic difluoromethylation of aromatic aldehydes using trimethyl (trifluoromethyl) silane (TMSCF3)
Journal of Fluorine Chemistry, 208, 10-14 (2018)
Oxidative trifluoromethylation and trifluoromethylthiolation reactions using (trifluoromethyl) trimethylsilane as a nucleophilic CF3 source
Accounts of Chemical Research, 47(5), 1513-1522 (2014)
Palladium-Catalyzed Oxidative Trifluoromethylation of Indoles at Room Temperature
Chemistry?A European Journal , 17(22), 6039-6042 (2011)
Trifluoromethylation of heterocumulenes with trimethyl (trifluoromethyl) silane in the presence of fluoride ions: synthesis of trifluoroacetamides and trifluorothioacetamides from isocyanates and isothiocyanates
Tetrahedron Letters, 42(46), 8181-8183 (2001)
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