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About This Item
线性分子式:
(CH3)3SiCF3
CAS号:
分子量:
142.19
Beilstein:
4241868
MDL编号:
UNSPSC代码:
12352101
PubChem化学物质编号:
NACRES:
NA.22
形式
liquid
质量水平
反应适用性
reaction type: C-C Bond Formation
IVD
for in vitro diagnostic use
浓度
2 M in THF
折射率
n20/D 1.386
密度
0.91 g/mL at 20 °C
SMILES字符串
C[Si](C)(C)C(F)(F)F
InChI
1S/C4H9F3Si/c1-8(2,3)4(5,6)7/h1-3H3
InChI key
MWKJTNBSKNUMFN-UHFFFAOYSA-N
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一般描述
Trimethyl(trifluoromethyl)silane (TMSCF3) is also called as Ruppert-Prakash fluorination reagent. It is extensively used for the synthesis of trifluoromethyl-containing compounds.
应用
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.
警示用语：
Danger
危险分类
Acute Tox. 4 Oral - Carc. 2 - Eye Irrit. 2 - Flam. Liq. 2 - STOT SE 3
靶器官
Respiratory system
补充剂危害
储存分类代码
3 - Flammable liquids
WGK
WGK 3
闪点(°F)
1.4 °F
闪点(°C)
-17 °C
个人防护装备
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
法规信息
危险化学品
Trifluoromethylation of non-activated aldimines with trimethyl (trifluoromethyl) silane in the presence of tetramethylammonium fluoride: A closer look into the reaction route
Kirij NV, et al.
Journal of Fluorine Chemistry, 129(1), 14-21 (2008)
Recent advances in transition-metal-catalyzed trifluoromethylation and related transformations
Chen P and Liu G
Synthesis, 45(21), 2919-2939 (2013)
Trifluoromethylation of heterocumulenes with trimethyl (trifluoromethyl) silane in the presence of fluoride ions: synthesis of trifluoroacetamides and trifluorothioacetamides from isocyanates and isothiocyanates
Kirij NV, et al.
Tetrahedron Letters, 42(46), 8181-8183 (2001)
Oxidative trifluoromethylation and trifluoromethylthiolation reactions using (trifluoromethyl) trimethylsilane as a nucleophilic CF3 source
Chu L and Qing F-L
Accounts of Chemical Research, 47(5), 1513-1522 (2014)
Palladium-Catalyzed Oxidative Trifluoromethylation of Indoles at Room Temperature
Mu X, et al.
Chemistry?A European Journal , 17(22), 6039-6042 (2011)
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