1-(4-Chloropyridin-2-yl)-N-methylmethanamine: Properties & Uses
1-(4-Chloropyridin-2-yl)-N-methylmethanamine: Properties & Uses
1-(4-Chloropyridin-2-yl)-N-methylmethanamine is a chlorinated pyridine-derived secondary amine that serves as a versatile synthetic building block in medicinal chemistry and drug discovery research.
- IUPAC Name
- 1-(4-Chloropyridin-2-yl)-N-methylmethanamine
- Molecular Formula
- C7H9ClN2
- Compound Class
- Chloropyridine / Secondary Amine
- Primary Application
- Synthetic intermediate and building block in medicinal chemistry
- Key Functional Groups
- Chloro substituent, pyridine ring, secondary amine (N-methyl)
- Aladdin SKU
- N690972
Chemical Identity and Structure
1-(4-Chloropyridin-2-yl)-N-methylmethanamine is a heterocyclic secondary amine featuring a pyridine ring substituted with a chlorine atom at the 4-position and a methylaminomethyl group at the 2-position. Its molecular formula is C7H9ClN2, combining the electron-deficient character of the chloropyridine scaffold with the nucleophilic reactivity of the secondary amine moiety.
The pyridine nitrogen and the pendant amine nitrogen together provide two distinct sites for coordination or further chemical transformation, making this molecule especially attractive as a bidentate ligand precursor or as a bifunctional intermediate in multi-step synthesis. The chloro substituent at the 4-position activates the ring toward nucleophilic aromatic substitution (SNAr), enabling selective displacement under appropriate reaction conditions.
Synthetic Applications and Reactivity
The compound's dual functionality — an electrophilic aromatic chloride and a nucleophilic secondary amine — positions it as a highly versatile intermediate in organic synthesis. The 4-chloro group participates readily in palladium-catalyzed cross-coupling reactions such as Suzuki–Miyaura, Buchwald–Hartwig, and Negishi couplings, allowing introduction of aryl, vinyl, or amino substituents onto the pyridine ring with high selectivity.
The secondary amine (N-methylaminomethyl) side chain can undergo acylation, sulfonylation, reductive amination, or alkylation to generate a wide range of structurally diverse analogues. This combination makes 1-(4-Chloropyridin-2-yl)-N-methylmethanamine particularly useful in library synthesis for lead optimization campaigns in drug discovery programs targeting CNS disorders, oncology, and infectious diseases, where pyridine-containing scaffolds are frequently encountered in approved therapeutics.
Handling, Storage, and Safety Considerations
As with most secondary amine-containing heterocycles, 1-(4-Chloropyridin-2-yl)-N-methylmethanamine should be handled under standard laboratory safety precautions. Use appropriate personal protective equipment (PPE) including nitrile gloves, safety goggles, and a lab coat. Operations generating aerosols or fine particulates should be performed in a well-ventilated fume hood.
The compound should be stored in a tightly sealed container away from oxidizing agents, strong acids, and strong bases. Storage under cool, dry, and dark conditions is recommended to preserve chemical integrity and minimize degradation over time. Researchers should consult the Safety Data Sheet (SDS) provided by Aladdin Scientific before first use and ensure compliance with local regulations for handling halogenated amines.
Quality Specifications and Ordering Information
Aladdin Scientific offers 1-(4-Chloropyridin-2-yl)-N-methylmethanamine under SKU N690972. Researchers and procurement teams are encouraged to contact Aladdin Scientific directly for the most current certificate of analysis (CoA), purity data, available pack sizes, and pricing information. Typical quality control parameters for this class of building blocks include purity assessment by HPLC, identity confirmation by 1H NMR and mass spectrometry, and water content determination by Karl Fischer titration where applicable.
For bulk or custom quantities required for larger synthesis campaigns, Aladdin Scientific's technical sales team can provide tailored quotations and discuss custom synthesis options to meet specific research project requirements.
Frequently asked questions
What type of compound is 1-(4-Chloropyridin-2-yl)-N-methylmethanamine?
It is a chlorinated pyridine-based secondary amine with molecular formula C7H9ClN2. The compound features an electron-deficient pyridine ring bearing a 4-chloro substituent and a methylaminomethyl group at the 2-position, making it a bifunctional building block for organic synthesis.
What are the main synthetic uses of this compound?
The 4-chloro group enables palladium-catalyzed cross-coupling reactions (e.g., Suzuki, Buchwald–Hartwig), while the secondary amine side chain can undergo acylation, sulfonylation, and reductive amination. These complementary reactivities make it valuable for constructing diverse heterocyclic libraries in medicinal chemistry and drug discovery.
How should 1-(4-Chloropyridin-2-yl)-N-methylmethanamine be stored?
The compound should be stored in a tightly sealed container under cool, dry, and dark conditions, away from oxidizing agents and strong acids or bases. Always consult the Aladdin Scientific SDS for full storage and handling guidance before use.
How can I obtain purity and analytical data for SKU N690972?
Aladdin Scientific provides a certificate of analysis (CoA) for each lot of N690972. Contact Aladdin Scientific's customer service or technical sales team with your lot number to request the CoA, which typically includes HPLC purity, NMR identity confirmation, and other relevant quality control data.
References
- General reference: March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 7th ed. Smith, M. B. Wiley, 2013. (Nucleophilic aromatic substitution and cross-coupling reactions of halopyridines.)
- Joule, J. A.; Mills, K. Heterocyclic Chemistry, 5th ed. Wiley-Blackwell, 2010. (Pyridine chemistry and reactivity of chloropyridine derivatives.)
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
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