188778
5-Amino-2-chloropyridine
98%
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About This Item
Empirical Formula (Hill Notation):
C5H5ClN2
CAS Number:
Molecular Weight:
128.56
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
226-322-3
Beilstein/REAXYS Number:
108891
MDL number:
Assay:
98%
Form:
solid
InChI key
QAJYCQZQLVENRZ-UHFFFAOYSA-N
InChI
1S/C5H5ClN2/c6-5-2-1-4(7)3-8-5/h1-3H,7H2
SMILES string
Nc1ccc(Cl)nc1
assay
98%
form
solid
mp
81-83 °C (lit.)
functional group
chloro
Quality Level
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
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)
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 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
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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