Description

3-Amino-2-bromo-5-chloropyridine (CAS No. 90902-83-3) is a high-purity halogenated pyridine derivative with the molecular formula C₅H₄BrClN₂, widely utilized in pharmaceutical and agrochemical research. This compound, also known by its IUPAC name 2-bromo-5-chloropyridin-3-amine, features a reactive amino group adjacent to bromo and chloro substituents, making it a versatile intermediate for nucleophilic substitution and cross-coupling reactions (e.g., Buchwald-Hartwig amination). Supplied as an off-white to light brown crystalline powder with ≥95% purity (HPLC), it is rigorously tested for heavy metals, residual solvents, and moisture content to ensure batch-to-batch consistency. Ideal for synthesizing bioactive molecules, it is packaged under inert gas in amber glass vials with optional argon-sealed options for air-sensitive applications. Store at 2-8°C in a dry environment.

Properties

• CAS Number: 90902-83-3
• Complexity: 101
• IUPAC Name: 2-bromo-5-chloro-pyridin-3-amine
• InChI: InChI=1S/C5H4BrClN2/c6-5-4(8)1-3(7)2-9-5/h1-2H,8H2
• InChI Key: AZOXQBMBDRLSCQ-UHFFFAOYSA-N
• Exact Mass: 205.92464
• Molecular Formula: C5H4BrClN2
• Molecular Weight: 207.45
• SMILES: C1=C(C=NC(=C1N)Br)Cl
• Topological: 38.9
• Monoisotopic Mass: 205.92464
• Synonyms: 3-AMINO-2-BROMO-5-CHLOROPYRIDINE, 90902-83-3, DTXSID30377813, DTXCID90328841, 674-547-4, 2-bromo-5-chloropyridin-3-amine, 2-Bromo-3-Amino-5-Chloropyridine, MFCD07368976, EN300-208882, 2-bromo-5-chloro-pyridin-3-amine, 3-Pyridinamine, 2-bromo-5-chloro-, 2-bromo-5-chloro-3-pyridylamine, 2-Bromo-5-chloropyridine-3-amine, SCHEMBL305370, AZOXQBMBDRLSCQ-UHFFFAOYSA-N, BDBM626096, 2-Bromo-5-chloro-pyridin-3-ylamine, SBB051899, AKOS015855685, DS-0697, SB78492, AC-24911, SY033433, TS-02963, DB-003884, CS-0042741

Application

3-Amino-2-bromo-5-chloropyridine serves as a key building block in medicinal chemistry for the development of kinase inhibitors and antimicrobial agents. Its halogenated pyridine core enables efficient Suzuki-Miyaura couplings to create biaryl scaffolds in drug candidates. Researchers also employ it in the synthesis of herbicides and fungicides due to its dual halogen reactivity. The compound’s amino group facilitates further derivatization via acylation or reductive amination for library synthesis.

Safety and Hazards

GHS Hazard Statements

• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (66.7%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

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

Hazard Classes and Categories

• Skin Irrit. 2 (100%)
• Eye Irrit. 2 (100%)
• STOT SE 3 (66.7%)

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