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777692

Sigma-Aldrich

(1,10-Phenanthroline)(trifluoromethyl)copper(I)

90%

Synonym(s):
Trifluoromethylator
Empirical Formula (Hill Notation):
C13H8CuF3N2
CAS Number:
Molecular Weight:
312.76
MDL number:
PubChem Substance ID:
NACRES:
NA.22

assay

90%

form

solid

storage temp.

2-8°C

InChI

1S/C12H8N2.CF3.Cu/c1-3-9-5-6-10-4-2-8-14-12(10)11(9)13-7-1;2-1(3)4;/h1-8H;;

InChI key

CUQZQRIIFNWQSJ-UHFFFAOYSA-N

General description

(1,10-Phenanthroline)(trifluoromethyl)copper(I) [(Phen)Cu-CF3] can be prepared by treating [CuOt-Bu]4 with 1,10-phenanthroline, followed by the addition of (trifluoromethyl)trimethylsilane (CF3TMS). It is an easily handled, thermally stable, single-component reagent.

Application

Trifluoromethylator, A New Arene Trifluoromethylation Reagent: (Phen)Cu-CF3

(Phen)Cu-CF3 can be used as a reagent for the trifluoromethylation of aryl iodides. Electron-rich and electron-deficient iodoarenes, as well as sterically-hindered iodoarenes, react in high yield under mild conditions. Electrophilic functional groups, including aldehydes, nitroarenes, ketones, and esters are tolerated. The substrate scope of this reagent is broad and the reagent has wide applicability for trifluoromethylation reactions.
It can also be used in the oxidative trifluoromethylation of organoboron reagents, and terminal alkynes through C-H activation.

Packaging

1, 10, 100 g in glass bottle
500 mg in glass insert

Legal Information

Trifluoromethylator is a registered trademark of Catylix, Inc

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

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(1, 10-Phenanthroline)(trifluoromethyl) copper (I)
Qing F-L
Encyclopedia of Reagents for Organic Synthesis, Second Edition, 1-4 (2001)
A broadly applicable copper reagent for trifluoromethylations and perfluoroalkylations of aryl iodides and bromides.
Hiroyuki Morimoto et al.
Angewandte Chemie (International ed. in English), 50(16), 3793-3798 (2011-03-29)

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