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91862

Sigma-Aldrich

三甲基(三氟甲基)硅烷 溶液

2 M in THF

同義詞:

(Trifluoromethyl)trimethylsilane, TFMTMS

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About This Item

線性公式:
(CH3)3SiCF3
CAS號碼:
分子量::
142.19
Beilstein:
4241868
MDL號碼:
分類程式碼代碼:
12352101
PubChem物質ID:
NACRES:
NA.22

形狀

liquid

反應適用性

reaction type: C-C Bond Formation

IVD

for in vitro diagnostic use

濃度

2 M in THF

折射率

n20/D 1.386

密度

0.91 g/mL at 20 °C

SMILES 字串

C[Si](C)(C)C(F)(F)F

InChI

1S/C4H9F3Si/c1-8(2,3)4(5,6)7/h1-3H3

InChI 密鑰

MWKJTNBSKNUMFN-UHFFFAOYSA-N

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相關類別

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:
  • 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


分析證明 (COA)

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Palladium-Catalyzed Oxidative Trifluoromethylation of Indoles at Room Temperature
Mu X, et al.
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
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)
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)
Recent advances in transition-metal-catalyzed trifluoromethylation and related transformations
Chen P and Liu G
Synthesis, 45(21), 2919-2939 (2013)

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