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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:
5350-93-6
Molecular Weight:
128.56
Beilstein:
108891
EC Number:
226-322-3
MDL number:
MFCD00006243
UNSPSC Code:
12352100
PubChem Substance ID:
24851317
NACRES:
NA.22

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
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

188778-VAR:
188778-BULK:
188778-1G:
188778-5G:

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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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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