188778
5-Amino-2-chloropyridine
98%
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About This Item
Fórmula empírica (notación de Hill):
C5H5ClN2
Número de CAS:
Peso molecular:
128.56
Beilstein/REAXYS Number:
108891
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
Productos recomendados
Quality Level
assay
98%
form
solid
mp
81-83 °C (lit.)
functional group
chloro
SMILES string
Nc1ccc(Cl)nc1
InChI
1S/C5H5ClN2/c6-5-2-1-4(7)3-8-5/h1-3H,7H2
InChI key
QAJYCQZQLVENRZ-UHFFFAOYSA-N
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General description
5-Amino-2-chloropyridine undergoes Suzuki-Miyaura coupling with sterically hindered 2,6-dimethylphenylboronic acid. It undergoes facile temperature dependent displacement of chloride by bromide via Sandmeyer reaction to yield 2,5-dibromopyridine.
Application
5-Amino-2-chloropyridine was used in the synthesis of [2H5]2-amino-l-methyl-6-phenylimidazo[4,5-b]pyridine. It was used in identification and evaluation of molecularly imprinted polymers for the selective removal of potentially genotoxic aminopyridine impurities from pharmaceuticals.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk_germany
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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Unexpected Displacements of Chloride by Bromide Found During Sandmeyer Reactions of 3-or 5-Amino-2-chloropyridines.
Krapcho AP and Haydar SN.
Heterocyclic Communications, 4(4), 291-292 (1998)
A M Lynch et al.
Cancer research, 52(22), 6216-6223 (1992-11-15)
During the cooking of beef, the genotoxic heterocyclic aromatic amines 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx), 2-amino-3,4,8-trimethylimidazo[4,5-f]quinoxaline (DiMeIQx), and 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) are formed. Little is known about the fate of these compounds in humans or the factors affecting it. We have developed assays based
Fast identification of selective resins for removal of genotoxic aminopyridine impurities via screening of molecularly imprinted polymer libraries.
Kecili R, et al. et al.
Journal of Chromatography A (2014)
A highly active catalyst for Suzuki-Miyaura cross-coupling reactions of heteroaryl compounds.
Kelvin L Billingsley et al.
Angewandte Chemie (International ed. in English), 45(21), 3484-3488 (2006-04-28)
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