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188778

Sigma-Aldrich

5-Amino-2-chloropyridine

98%

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About This Item

Empirical Formula (Hill Notation):
C5H5ClN2
CAS Number:
Molecular Weight:
128.56
Beilstein/REAXYS Number:
108891
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

98%

form

solid

mp

81-83 °C (lit.)

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.

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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
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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