2-Bromo-N-methylpyridin-4-amine: Handling & Use Guidelines
2-Bromo-N-methylpyridin-4-amine: Handling & Use Guidelines
2-Bromo-N-methylpyridin-4-amine is a halogenated aminopyridine building block widely employed in medicinal chemistry and synthetic organic chemistry as a versatile intermediate for transition-metal-catalyzed cross-coupling reactions and heterocyclic library construction.
- Chemical Name
- 2-Bromo-N-methylpyridin-4-amine
- SKU
- B195271
- Molecular Formula
- C6H7BrN2
- Molecular Weight
- 187.04 g/mol
- Key Functional Groups
- Aryl bromide, secondary amine (N-methylamino)
- Primary Applications
- Cross-coupling reactions, pharmaceutical intermediate synthesis, heterocyclic chemistry
- Recommended Storage
- Cool, dry place; sealed container; away from light and moisture
Chemical Identity and Structural Features
2-Bromo-N-methylpyridin-4-amine (SKU B195271; molecular formula C6H7BrN2; MW 187.04 g/mol) is a pyridine derivative bearing two key functional handles: an aryl bromide at the 2-position and an N-methylamino group at the 4-position. The electron-donating methylamino substituent and the electron-withdrawing pyridine ring nitrogen create a polarized electronic environment that facilitates selective reactivity at the C–Br bond under transition-metal catalysis. The compound is typically presented as a solid at room temperature and should be characterized by melting point, 1H NMR, and HPLC purity analysis upon receipt to confirm identity and quality before use.
Applications in Synthetic and Medicinal Chemistry
The aryl bromide moiety of 2-Bromo-N-methylpyridin-4-amine makes it a productive partner in palladium-catalyzed cross-coupling reactions, including Suzuki–Miyaura, Buchwald–Hartwig amination, and Negishi couplings, enabling rapid diversification of the pyridine core. The N-methylamino group at the 4-position can itself serve as a handle for further functionalization, such as acylation or sulfonylation, expanding structural diversity. This combination of reactive sites renders the compound particularly valuable in medicinal chemistry programs aimed at generating drug-like pyridine-containing scaffolds for kinase inhibitor, GPCR modulator, and other target-focused libraries. Researchers should optimize catalyst loading, ligand choice, and base selection empirically for each specific transformation.
Handling, Safety, and Storage Protocols
All work with 2-Bromo-N-methylpyridin-4-amine should be conducted in a well-ventilated fume hood. Appropriate personal protective equipment (PPE) — including chemical-resistant gloves, laboratory coat, and safety glasses — must be worn at all times. As with all organobromine and amine-containing compounds, avoid inhalation of dust or aerosols and prevent contact with skin and eyes. In the event of skin contact, wash thoroughly with soap and water; for eye contact, rinse immediately with copious water and seek medical advice. The compound should be stored in a tightly sealed container in a cool (2–8 °C recommended for long-term stability), dry, and well-ventilated location away from incompatible materials such as strong oxidizers and strong acids. Refer to the Safety Data Sheet (SDS) provided by Aladdin Scientific for complete hazard classification and first-aid measures before use.
Quality Verification and Analytical Recommendations
Upon receipt of 2-Bromo-N-methylpyridin-4-amine (B195271), researchers are advised to verify compound identity and purity using the following analytical methods: (1) 1H NMR spectroscopy to confirm the expected aromatic proton pattern, N–CH3 singlet, and N–H signal; (2) HPLC analysis with a suitable reversed-phase column to assess purity (≥95% is typical for research-grade material, but verify the certificate of analysis [CoA] supplied with the batch); (3) GC–MS or LC–MS to confirm the molecular ion consistent with MW 187.04 and the characteristic bromine isotope pattern (M and M+2 in approximately 1:1 ratio). Keep a record of the CoA lot number and storage conditions for traceability and reproducibility of results. Contact Aladdin Scientific technical support if analytical data deviate significantly from expected values.
Procurement and Ordering Information
2-Bromo-N-methylpyridin-4-amine is available from Aladdin Scientific under SKU B195271. Researchers and procurement officers should quote this SKU when placing orders to ensure the correct product, grade, and packaging are supplied. Multiple pack sizes may be available to suit scale requirements from small exploratory reactions to larger-scale synthesis campaigns; contact Aladdin Scientific sales for current availability, pricing, and lead times. For questions regarding specification sheets, certificates of analysis, or custom synthesis inquiries, reach out to Aladdin Scientific technical or customer service teams. Aladdin Scientific's reward points, promotional pricing, and institutional account programs may apply — consult the Aladdin Scientific website or your account manager for details.
Frequently asked questions
What reactions is 2-Bromo-N-methylpyridin-4-amine (B195271) most commonly used for?
It is primarily used as an aryl bromide partner in palladium-catalyzed cross-coupling reactions such as Suzuki–Miyaura, Buchwald–Hartwig amination, and Negishi couplings. The N-methylamino group can additionally be functionalized via acylation or sulfonylation to build more complex molecular architectures.
How should 2-Bromo-N-methylpyridin-4-amine be stored to maintain stability?
The compound should be stored in a tightly sealed container under cool (2–8 °C recommended for long-term storage), dry, and dark conditions away from strong oxidizers and strong acids. Always check the Aladdin Scientific certificate of analysis for any lot-specific storage recommendations.
How can I confirm the identity and purity of the received batch of B195271?
Identity and purity can be confirmed using 1H NMR (to verify the aromatic proton pattern, N-CH3 singlet, and N-H signal), HPLC (purity typically ≥95% for research-grade material), and GC-MS or LC-MS (to confirm MW 187.04 and the characteristic 1:1 bromine isotope pattern). Always cross-reference results against the certificate of analysis provided with the batch.
Is 2-Bromo-N-methylpyridin-4-amine available in multiple pack sizes?
Multiple pack sizes may be available to accommodate different research scales. Please contact Aladdin Scientific sales or visit the product page for SKU B195271 to check current availability, pricing, and lead times for your required quantity.
What personal protective equipment (PPE) is required when handling this compound?
At minimum, chemical-resistant gloves, a laboratory coat, and safety glasses should be worn. All manipulations should be performed in a well-ventilated fume hood. Consult the Aladdin Scientific Safety Data Sheet (SDS) for B195271 for complete hazard information and first-aid procedures.
References
- Aladdin Scientific. Product Information: 2-Bromo-N-methylpyridin-4-amine, SKU B195271. Aladdin Scientific Corp.
- Miyaura, N.; Suzuki, A. Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds. Chemical Reviews 1995, 95 (7), 2457–2483. doi:10.1021/cr00039a007
- Hartwig, J. F. Evolution of a Fourth Generation Catalyst for the Amination and Thioetherification of Aryl Halides. Accounts of Chemical Research 2008, 41 (11), 1534–1544. doi:10.1021/ar800098p
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
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