91862
三甲基（三氟甲基）硅烷 溶液
2 M in THF
别名:
(Trifluoromethyl)trimethylsilane, TFMTMS
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关于此项目
线性分子式:
(CH3)3SiCF3
化学文摘社编号:
分子量:
142.19
UNSPSC Code:
12352101
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
4241868
InChI
1S/C4H9F3Si/c1-8(2,3)4(5,6)7/h1-3H3
SMILES string
C[Si](C)(C)C(F)(F)F
InChI key
MWKJTNBSKNUMFN-UHFFFAOYSA-N
form
liquid
reaction suitability
reaction type: C-C Bond Formation
IVD
for in vitro diagnostic use
concentration
2 M in THF
refractive index
n20/D 1.386
density
0.91 g/mL at 20 °C
functional group
fluoro
Quality Level
General description
Trimethyl(trifluoromethyl)silane (TMSCF3) is also called as Ruppert-Prakash fluorination reagent. It is extensively used for the synthesis of trifluoromethyl-containing compounds.
Application
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.
signalword
Danger
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Carc. 2 - Eye Irrit. 2 - Flam. Liq. 2 - STOT SE 3
target_organs
Respiratory system
supp_hazards
存储类别
3 - Flammable liquids
wgk
WGK 3
flash_point_f
1.4 °F
flash_point_c
-17 °C
ppe
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
法规信息
危险化学品
此项目有
Nucleophilic difluoromethylation of aromatic aldehydes using trimethyl (trifluoromethyl) silane (TMSCF3)
Krishnamoorthy S, et al.
Journal of Fluorine Chemistry, 208, 10-14 (2018)
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)
Organocatalyzed Regio-and Enantioselective Allylic Trifluoromethylation of Morita-Baylis-Hillman Adducts Using Ruppert-Prakash Reagent
Furukawa T, et al.
Organic Letters, 13(15), 3972-3975 (2011)
Palladium-Catalyzed Oxidative Trifluoromethylation of Indoles at Room Temperature
Mu X, et al.
Chemistry?A European Journal , 17(22), 6039-6042 (2011)
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)
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