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Sigma-Aldrich

4,7-Dimethoxy-1,10-phenanthroline

97%

Sinônimo(s):

4,7-Dimethoxy-1,10-phenanthrolin

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About This Item

Fórmula empírica (Notação de Hill):
C14H12N2O2
Número CAS:
92149-07-0
Peso molecular:
240.26
Número MDL:
MFCD00233883
Código UNSPSC:
12352300
ID de substância PubChem:
24885413
NACRES:
NA.22

Ensaio

97%

forma

solid

adequação da reação

reagent type: ligand

pf

197-212 °C

cadeia de caracteres SMILES

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

chave InChI

ZPGVCQYKXIQWTP-UHFFFAOYSA-N

Categorias relacionadas

Descrição geral

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.

Aplicação

Ligand for Cu-catalzyed N-arylation of imidazoles

Palavra indicadora

Danger

Frases de perigo

H302,H318,H400

Classificações de perigo

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

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

dust mask type N95 (US), Eyeshields, Gloves

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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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