2-Chloro-5-methoxypyridin-4-amine: Properties & Lab FAQ

2-Chloro-5-methoxypyridin-4-amine is a halogenated aminopyridine building block widely used in medicinal chemistry and pharmaceutical synthesis as a versatile intermediate for constructing bioactive heterocyclic scaffolds.

Chemical Name

2-Chloro-5-methoxypyridin-4-amine

SKU / Catalog Number

C692159

Molecular Formula

C6H7ClN2O

Molecular Weight

158.58 g/mol

Functional Groups

Primary amine, aryl chloride, methoxy ether on pyridine ring

Primary Application

Pharmaceutical intermediate and heterocyclic building block in medicinal chemistry

Chemical Identity and Structure

2-Chloro-5-methoxypyridin-4-amine (CAS catalog SKU C692159) is a substituted pyridine bearing three key functional groups: a primary amino group at the 4-position, a chlorine substituent at the 2-position, and a methoxy group at the 5-position. The molecular formula is C6H7ClN2O with a molecular weight of approximately 158.58 g/mol. The combination of an electron-donating amino group and an electron-withdrawing ring nitrogen creates a polarized aromatic system that is highly amenable to nucleophilic aromatic substitution (SNAr) at the C-2 chlorine, as well as transition-metal-catalyzed cross-coupling reactions. The methoxy group at C-5 further modulates ring electronics and can serve as a handle for subsequent synthetic elaboration.

Handling, Storage, and Safety

As with most halogenated aromatic amines, 2-Chloro-5-methoxypyridin-4-amine should be handled in a well-ventilated fume hood with appropriate personal protective equipment, including nitrile gloves, safety glasses, and a lab coat. Aromatic amines as a chemical class may present sensitization or irritation hazards; consult the Safety Data Sheet (SDS) supplied with the product before use.

For storage, keep the compound in a tightly sealed container away from moisture, heat, and light. Storage at 2–8 °C under an inert atmosphere (nitrogen or argon) is recommended to preserve reagent integrity over extended periods. Always verify specific storage conditions on the product label and SDS, as lot-specific recommendations may apply.

Applications in Medicinal Chemistry and Synthesis

2-Chloro-5-methoxypyridin-4-amine is a valued building block in medicinal chemistry programs targeting kinase inhibitors, antiviral agents, and other bioactive small molecules that incorporate aminopyridine pharmacophores. The C-2 chlorine is readily displaced by nitrogen, oxygen, or sulfur nucleophiles under SNAr conditions, or can participate in palladium-catalyzed Suzuki, Buchwald-Hartwig, and related coupling reactions to install diverse aryl, heteroaryl, or amine substituents.

The free primary amine at C-4 allows direct acylation, sulfonylation, or reductive amination, enabling rapid diversification of the core scaffold. These orthogonal reactivity profiles make the compound especially useful in parallel synthesis and structure-activity relationship (SAR) campaigns.

Purity, Quality, and Ordering Information

Aladdin Scientific supplies 2-Chloro-5-methoxypyridin-4-amine under catalog number C692159. Purity specifications and available pack sizes should be confirmed on the current product page or by contacting Aladdin customer service, as these details are subject to change between production lots. Certificate of Analysis (CoA) documents, including characterization data such as HPLC purity, NMR, and GC-MS where applicable, are available on request.

For bulk or custom quantities, procurement teams are encouraged to contact Aladdin Scientific directly to discuss pricing, lead times, and any required quality documentation such as GMP certificates or regulatory filing support.

Frequently asked questions

What is the molecular formula and molecular weight of 2-Chloro-5-methoxypyridin-4-amine?

The molecular formula of 2-Chloro-5-methoxypyridin-4-amine is C6H7ClN2O, giving a molecular weight of approximately 158.58 g/mol. These values are based on standard atomic weights for carbon, hydrogen, chlorine, nitrogen, and oxygen.

How should 2-Chloro-5-methoxypyridin-4-amine be stored to maintain stability?

The compound should be stored in a tightly sealed container at 2–8 °C, protected from moisture, heat, and light, preferably under an inert atmosphere such as nitrogen or argon. Always refer to the product label and the current SDS for lot-specific storage recommendations.

What types of chemical reactions can 2-Chloro-5-methoxypyridin-4-amine participate in?

This compound is reactive at multiple sites: the C-2 aryl chloride undergoes nucleophilic aromatic substitution (SNAr) with heteroatom nucleophiles and participates in palladium-catalyzed cross-coupling reactions such as Suzuki and Buchwald-Hartwig amination. The C-4 primary amine is available for acylation, sulfonylation, and reductive amination, providing orthogonal handles for scaffold diversification in drug discovery programs.

Where can I obtain a Certificate of Analysis (CoA) for catalog number C692159?

Certificates of Analysis for C692159 are available through the Aladdin Scientific website product page or upon direct request to Aladdin customer service. Please have your lot number ready to ensure you receive documentation specific to your batch.

Is 2-Chloro-5-methoxypyridin-4-amine suitable for use as a pharmaceutical intermediate?

Yes, 2-Chloro-5-methoxypyridin-4-amine is widely recognized as a useful pharmaceutical intermediate and building block for constructing aminopyridine-containing drug candidates. For GMP-grade material or regulatory documentation requirements, contact Aladdin Scientific to discuss available quality grades and supporting documentation.

References

1. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. Wiley-Interscience. General reference for nucleophilic aromatic substitution and cross-coupling reactions of halogenated heteroaromatics.
2. Aladdin Scientific product page for 2-Chloro-5-methoxypyridin-4-amine, SKU C692159. Aladdin Scientific.

Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.