3-Amino-5-bromo-2-methoxypyridine: Lab Handling & Usage Guide

3-Amino-5-bromo-2-methoxypyridine is a halogenated, amino-substituted methoxypyridine building block widely employed in medicinal chemistry and heterocyclic synthesis as a versatile intermediate for constructing biologically active compounds.

Product SKU

B590515

Chemical Name

3-Amino-5-bromo-2-methoxypyridine

Reference Code

BD25474

Compound Class

Halogenated aminopyridine; heterocyclic building block

Primary Application

Pharmaceutical intermediate and medicinal chemistry synthesis

Functional Groups

Primary amine (–NH₂), bromo (–Br), methoxy (–OCH₃), pyridine ring

Chemical Identity and Key Properties

3-Amino-5-bromo-2-methoxypyridine is a pyridine derivative bearing three distinct functional handles: a primary amino group at the 3-position, a bromine substituent at the 5-position, and a methoxy group at the 2-position. This combination of nucleophilic (–NH₂), electrophilic (C–Br), and directing (–OCH₃) groups makes the compound an exceptionally versatile scaffold in synthetic chemistry.

The aromatic pyridine ring confers thermal stability, while the bromo substituent serves as a handle for cross-coupling reactions (e.g., Suzuki, Buchwald-Hartwig, Negishi). The free primary amine allows acylation, reductive amination, or condensation reactions, and the methoxy group can participate in SNAr chemistry under appropriate conditions. Researchers should verify specific physical constants (melting point, purity specification) from the current certificate of analysis supplied with product SKU B590515.

Storage, Handling, and Safety Guidelines

Storage: Store 3-Amino-5-bromo-2-methoxypyridine in a tightly sealed container in a cool, dry, and well-ventilated area, away from moisture, heat sources, and incompatible oxidizing agents. Refrigerated storage (2–8 °C) is typically recommended for extended shelf life; consult the product label and certificate of analysis for confirmed storage conditions for lot B590515.

Personal Protective Equipment (PPE): Always wear appropriate PPE when handling this compound, including nitrile gloves, a laboratory coat, and safety glasses or a face shield. Work in a chemical fume hood to minimize inhalation exposure to dust or vapors.

Waste Disposal: Dispose of waste material in accordance with local, regional, and national regulations governing halogenated organic compounds. Do not pour down the drain. Consult your institution's Environmental Health and Safety (EHS) office for guidance.

Review flag: Specific GHS hazard classification, H-statements, and P-statements should be confirmed from the current Safety Data Sheet (SDS) for SKU B590515 prior to use.

Synthetic Applications and Reaction Protocols

3-Amino-5-bromo-2-methoxypyridine is primarily used as a building block in the preparation of pharmaceutical candidates and agrochemical intermediates. The three reactive sites can be exploited either independently or in sequence:

• Palladium-catalyzed cross-coupling at C5–Br: The aryl bromide undergoes Suzuki-Miyaura coupling with aryl- or heteroarylboronic acids, Negishi coupling with organozinc reagents, or Buchwald-Hartwig amination with secondary amines under standard palladium/phosphine catalyst systems. Typical base: K₂CO₃ or Cs₂CO₃; typical solvent: DMF, dioxane, or toluene; temperature: 80–110 °C.
• Functionalization of the 3-amino group: The primary amine can be converted to amides via reaction with acid chlorides or anhydrides, to ureas via reaction with isocyanates, or used in reductive amination to introduce secondary or tertiary amine motifs.
• SNAr at C2–OCH₃: Under forcing conditions, the methoxy group can be displaced by strong nitrogen or oxygen nucleophiles in aromatic nucleophilic substitution, enabling further diversification of the pyridine ring.

Researchers should optimize reaction conditions empirically and confirm purity of the starting material by HPLC or NMR prior to use in multi-step sequences.

Quality Verification and Analytical Characterization

Before incorporating 3-Amino-5-bromo-2-methoxypyridine (SKU B590515) into a synthetic route, verify the following:

1. Identity confirmation: Use ¹H NMR and ¹³C NMR spectroscopy to confirm the pyridine ring proton pattern, the singlet corresponding to –OCH₃ (typically ~δ 3.9 ppm), and NH₂ resonances. Mass spectrometry (ESI-MS or EI-MS) should show the expected molecular ion with the characteristic bromine isotope pattern (M and M+2 in ~1:1 ratio).
2. Purity assessment: Reverse-phase HPLC with UV detection at 254 nm is recommended. Acceptable purity thresholds depend on the intended application; for pharmaceutical synthesis, ≥98% purity (as stated on the certificate of analysis) is typically required.
3. Moisture content: As an amine-containing compound, moisture uptake can affect reactivity. Karl Fischer titration may be used to determine water content if the compound has been stored under non-ideal conditions.

Always request and retain the certificate of analysis (CoA) for each lot received. Contact Aladdin Scientific's technical support team if analytical data do not meet specifications.

Frequently asked questions

What cross-coupling reactions are compatible with 3-Amino-5-bromo-2-methoxypyridine?

The C5 aryl bromide of 3-Amino-5-bromo-2-methoxypyridine is compatible with palladium-catalyzed Suzuki-Miyaura, Negishi, and Buchwald-Hartwig coupling reactions. Standard Pd/phosphine ligand systems in polar aprotic or ethereal solvents at 80–110 °C are typically employed. The free amine group may require protection (e.g., as a Boc carbamate) depending on the sensitivity of the coupling partner.

How should 3-Amino-5-bromo-2-methoxypyridine be stored to maintain stability?

Store the compound in a tightly sealed container at 2–8 °C in a cool, dry, and dark environment, away from oxidizing agents and moisture. Always confirm the recommended storage conditions stated on the product label and certificate of analysis for each specific lot of SKU B590515. For long-term storage, inert atmosphere conditions (e.g., argon or nitrogen) may be advisable.

Can the amino group of 3-Amino-5-bromo-2-methoxypyridine be selectively functionalized without affecting the aryl bromide?

Yes, the primary amine at the 3-position can typically be selectively acylated, sulfonylated, or reductively aminated under mild conditions that do not activate the aryl C–Br bond. For example, treatment with acyl chlorides in the presence of a base (e.g., triethylamine) at or below room temperature generally leaves the C–Br intact. Researchers should empirically optimize conditions and monitor reactions by TLC or HPLC to confirm selectivity.

What analytical methods are recommended to confirm the identity and purity of this compound?

¹H NMR and ¹³C NMR are recommended for structural identity confirmation, along with ESI mass spectrometry to verify the molecular weight and the characteristic bromine isotope pattern. Purity should be determined by reverse-phase HPLC with UV detection. The certificate of analysis for lot B590515 should be consulted for the reported purity value and analytical data.

Is 3-Amino-5-bromo-2-methoxypyridine available from Aladdin Scientific, and what is the product SKU?

Yes, 3-Amino-5-bromo-2-methoxypyridine is available from Aladdin Scientific under SKU B590515 (reference code BD25474). Contact Aladdin Scientific's sales or technical team for current pricing, available pack sizes, and lead times.

References

1. Aladdin Scientific product page and certificate of analysis for 3-Amino-5-bromo-2-methoxypyridine, SKU B590515, reference BD25474.
2. Miyaura, N.; Suzuki, A. Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds. Chemical Reviews, 1995, 95(7), 2457–2483. doi:10.1021/cr00039a007
3. Buchwald, S. L.; Mauger, C.; Mignani, G.; Scholz, U. Industrial-Scale Palladium-Catalyzed Coupling of Aryl Halides and Amines. Advanced Synthesis & Catalysis, 2006, 348(1-2), 23–39.

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