Description

3-Amino-2-bromo-6-chloropyridine (CAS No. 1050501-88-6) is a high-purity halogenated pyridine derivative with the molecular formula C₅H₄BrClN₂. This compound, also known by its IUPAC name 2-bromo-6-chloropyridin-3-amine, is a versatile building block in pharmaceutical and agrochemical synthesis. Its unique structure, featuring both bromo and chloro substituents adjacent to an amino group, enables selective functionalization for complex heterocyclic systems. Available in ≥95% purity (HPLC), this off-white to light yellow crystalline powder is packaged under inert gas to ensure stability. Ideal for Suzuki couplings, Buchwald-Hartwig aminations, and other cross-coupling reactions. Storage recommendation: 2-8°C in a tightly sealed container. Molecular Weight: 207.46 g/mol. Melting Point: 98-102°C. Hazard statements apply – consult SDS for handling precautions.

Properties

• CAS Number: 1050501-88-6
• Complexity: 101
• IUPAC Name: 2-bromo-6-chloro-pyridin-3-amine
• InChI: InChI=1S/C5H4BrClN2/c6-5-3(8)1-2-4(7)9-5/h1-2H,8H2
• InChI Key: OPKKXWUGXHSFQI-UHFFFAOYSA-N
• Exact Mass: 205.92464
• Molecular Formula: C5H4BrClN2
• Molecular Weight: 207.45
• SMILES: C1=CC(=NC(=C1N)Br)Cl
• Topological: 38.9
• Monoisotopic Mass: 205.92464
• Synonyms: 3-AMINO-2-BROMO-6-CHLOROPYRIDINE, 824-001-8, 2-bromo-6-chloropyridin-3-amine, 1050501-88-6, 2-BROMO-6-CHLORO-3-PYRIDINAMINE, 3-AMINO-6-CHLORO-2-BROMOPYRIDINE, MFCD11504927, 2-BROMO-6-CHLORO-PYRIDIN-3-YLAMINE, SCHEMBL2419164, DTXSID70670370, OPKKXWUGXHSFQI-UHFFFAOYSA-N, AKOS015854986, AC-6256, FA55774, FS-4691, PB34600, SY027968, CS-0054821, EN300-117822

Application

3-Amino-2-bromo-6-chloropyridine serves as a key intermediate in the synthesis of biologically active compounds, particularly in development of kinase inhibitors and antimicrobial agents. Its halogenated structure makes it valuable for palladium-catalyzed cross-coupling reactions in medicinal chemistry. Researchers utilize this compound to construct complex pyridine scaffolds for drug discovery programs targeting CNS disorders and inflammatory diseases. The presence of both bromo and chloro substituents allows sequential functionalization in multi-step synthetic routes.

Safety and Hazards

GHS Hazard Statements

• H302+H312+H332 (100%): Harmful if swallowed, in contact with skin or if inhaled [Warning Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]
• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

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