What Is 6-Chloro-5-methyl-3-nitropyridin-2-amine?

6-Chloro-5-methyl-3-nitropyridin-2-amine (CAS catalog SKU: C730183) is a pyridine derivative bearing three key functional groups on the ring: a primary amino group at position 2, a nitro group at position 3, a methyl substituent at position 5, and a chloro leaving group at position 6. This combination of electron-withdrawing (nitro, chloro) and electron-donating (amino) substituents makes the molecule highly reactive and valuable as a building block in multi-step organic synthesis. It belongs to the broader class of halogenated aminonitropyridines that serve as key intermediates in the preparation of pharmaceuticals, agrochemicals, and functional heterocyclic materials.

Physicochemical Properties and Structure

The molecular formula of 6-Chloro-5-methyl-3-nitropyridin-2-amine is C₆H₆ClN₃O₂, with a molecular weight of approximately 187.58 g/mol. The compound is a solid at room temperature and typically appears as a yellow to orange crystalline powder, consistent with the chromophoric contribution of the nitro group conjugated with the pyridine ring system. The presence of both the amino group (hydrogen-bond donor) and the nitro group (hydrogen-bond acceptor) influences its solubility profile: it shows limited solubility in water but is generally soluble in polar aprotic solvents such as DMSO, DMF, and acetonitrile. Researchers should confirm exact purity and analytical specifications (HPLC, NMR) from the product Certificate of Analysis (CoA) provided by Aladdin Scientific.

Synthetic Applications and Research Uses

The three reactive sites on 6-Chloro-5-methyl-3-nitropyridin-2-amine make it a versatile precursor in heterocyclic synthesis. The C6 chloro group is susceptible to nucleophilic aromatic substitution (SNAr), enabling introduction of amines, thiols, or alkoxides to diversify the pyridine scaffold. The C2 amino group can participate in condensation reactions, reductive aminations, or cyclization strategies to form fused ring systems such as imidazopyridines or pyrrolopyridines. The nitro group at C3 can be selectively reduced to an amine, providing a diamine intermediate for further functionalization or ring closure. These attributes collectively make the compound relevant in lead optimization programs in medicinal chemistry, particularly where pyridine-based pharmacophores are required.

Handling, Storage, and Safety Guidelines

As with all nitroaromatic compounds, 6-Chloro-5-methyl-3-nitropyridin-2-amine should be handled with appropriate laboratory precautions. Personnel should wear suitable personal protective equipment (PPE) including gloves, safety goggles, and a lab coat. Work should be performed in a well-ventilated fume hood to minimize inhalation exposure. The compound should be stored in a cool, dry location away from strong reducing agents, heat sources, and direct light, ideally at 2–8 °C or as specified on the product label. Users must consult the Safety Data Sheet (SDS) provided by Aladdin Scientific for comprehensive hazard, first-aid, and disposal information before use. Waste disposal must comply with applicable local regulations for halogenated and nitro-containing organic compounds.

Note: Specific GHS hazard classifications and pictograms should be verified against the current SDS for SKU C730183.

Ordering and Quality Assurance at Aladdin Scientific

6-Chloro-5-methyl-3-nitropyridin-2-amine is available from Aladdin Scientific under SKU C730183. Each batch is supported by a Certificate of Analysis (CoA) documenting purity and identity confirmation by standard analytical techniques. Researchers and procurement teams can place orders through the Aladdin Scientific website or by contacting the sales team directly. For custom quantities, bulk pricing, or specific purity requirements, customers are encouraged to reach out to technical support. Aladdin Scientific's quality management system ensures consistent lot-to-lot reproducibility critical for research applications.