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678023

Sigma-Aldrich

4,7-Dimethoxy-1,10-phenanthroline

97%

Synonym(s):

4,7-Dimethoxy-1,10-phenanthrolin

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About This Item

Empirical Formula (Hill Notation):
C14H12N2O2
CAS Number:
92149-07-0
Molecular Weight:
240.26
MDL number:
MFCD00233883
UNSPSC Code:
12352300
PubChem Substance ID:
24885413
NACRES:
NA.22

Quality Level

100

Assay

97%

form

solid

reaction suitability

reagent type: ligand

mp

197-212 °C

SMILES string

COc1ccnc2c1ccc3c(OC)ccnc23

InChI

1S/C14H12N2O2/c1-17-11-5-7-15-13-9(11)3-4-10-12(18-2)6-8-16-14(10)13/h3-8H,1-2H3

InChI key

ZPGVCQYKXIQWTP-UHFFFAOYSA-N

Related Categories

General description

4,7-Dimethoxy-1,10-phenanthroline is an organic compound that is used as an efficient ligand in organic synthesis. It is used in the N-arylation of imidazole with aryl iodides and bromides in the presence of copper catalysts. Various hindered and functionalized imidazoles and aryl halides were converted using this catalyst.

Application

Ligand for Cu-catalzyed N-arylation of imidazoles

Signal Word

Danger

Hazard Statements

H302,H318,H400

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1 - Eye Dam. 1

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Artis Klapars et al.
Journal of the American Chemical Society, 124(25), 7421-7428 (2002-06-20)
An experimentally simple and inexpensive catalyst system was developed for the amidation of aryl halides by using 0.2-10 mol % of CuI, 5-20 mol % of a 1,2-diamine ligand, and K(3)PO(4), K(2)CO(3), or Cs(2)CO(3) as base. Catalyst systems based on
Li, C. S.; Dixon, D. D.
Tetrahedron Letters, 45, 4257-4257 (2004)
Ryan A Altman et al.
Organic letters, 9(4), 643-646 (2007-02-09)
With use of Cu-based catalysts, 2- and 4-hydroxypyridines were N-arylated in modest to excellent yields. In the case of 2-hydroxypyridine, the use of 4,7-dimethoxy-1,10-phenanthroline, 3, expanded the scope of previous literature reports to include the use of N-containing heteroaryl halides
Ryan A Altman et al.
Organic letters, 8(13), 2779-2782 (2006-06-16)
[reaction: see text] 4,7-Dimethoxy-1,10-phenanthroline (L) was found to be an efficient ligand for the copper-catalyzed N-arylation of imidazole with aryl iodides and bromides under mild conditions. A variety of hindered and functionalized imidazoles and aryl halides were transformed in good
Ryan A Altman et al.
The Journal of organic chemistry, 72(16), 6190-6199 (2007-07-13)
4,7-Dimethoxy-1,10-phenanthroline (L1c) was found to be an efficient ligand for the copper-catalyzed N-arylation of imidazoles and benzimidazoles with both aryl iodides and bromides under mild conditions. Further optimization of the system has revealed that the addition of poly(ethylene glycol) accelerates

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