Description

2-Amino-5-bromo-3-iodopyridine (CAS No. 381233-96-1) is a high-purity halogenated pyridine derivative with the molecular formula C₅H₄BrIN₂. This compound, also known by its IUPAC name 5-bromo-3-iodopyridin-2-amine, is a versatile building block for pharmaceutical and agrochemical synthesis. Its unique structure, featuring both bromo and iodo substituents on the pyridine ring, allows for selective functionalization via cross-coupling reactions (e.g., Suzuki, Stille, or Sonogashira). Supplied as an off-white to light brown crystalline powder with ≥95% purity (HPLC), it is ideal for researchers developing kinase inhibitors, antiviral agents, or PET radioligands. Packaged under inert gas in amber glass vials to ensure stability, this product is characterized by ¹H/¹³C NMR, LC-MS, and elemental analysis.

Properties

• CAS Number: 381233-96-1
• Complexity: 101
• IUPAC Name: 5-bromo-3-iodo-pyridin-2-amine
• InChI: InChI=1S/C5H4BrIN2/c6-3-1-4(7)5(8)9-2-3/h1-2H,(H2,8,9)
• InChI Key: XPERZSKJGNUSHI-UHFFFAOYSA-N
• Exact Mass: 297.86026
• Molecular Formula: C5H4BrIN2
• Molecular Weight: 298.91
• SMILES: C1=C(C=NC(=C1I)N)Br
• Topological: 38.9
• Monoisotopic Mass: 297.86026
• Synonyms: 2-Amino-5-bromo-3-iodopyridine, 381233-96-1, DTXSID90363974, DTXCID00315020, 622-993-5, 5-Bromo-3-iodopyridin-2-amine, 2-Amino-3-iodo-5-bromopyridine, 5-bromo-3-iodo-pyridin-2-ylamine, MFCD06659000, 2-Pyridinamine, 5-bromo-3-iodo-, 2-Amine-5-bromo-3-iodopyridine, SCHEMBL402578, SCHEMBL4618937, 5-Bromo-3-iodopyridin-2-amino, 5-Bromo-3-iodopyridine-2-amine, XPERZSKJGNUSHI-UHFFFAOYSA-N, BCP23244, BBL103663, STL557473, AKOS005257759, AB25852, AC-9126, CS-W003313, FA09641, GS-6810, 2-Amino-5-bromo-3-iodopyridine, 97%, SY028356, DB-032285, EN300-86176

Application

2-Amino-5-bromo-3-iodopyridine serves as a key intermediate in medicinal chemistry, particularly for synthesizing kinase-targeting drugs due to its hydrogen-bonding capable amino group and halogen-rich scaffold. The compound’s orthogonal halogen substituents enable sequential palladium-catalyzed couplings to create diverse biaryl structures. It is also employed in radiopharmaceutical development, where the iodine moiety allows for isotopic exchange with ¹²⁵I or ¹²³I for imaging applications.

Safety and Hazards

GHS Hazard Statements

• H302 (85.4%): Harmful if swallowed [Warning Acute toxicity, oral]
• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H318 (83.3%): Causes serious eye damage [Danger Serious eye damage/eye irritation]
• H319 (16.7%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (97.9%): 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, P305+P354+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Acute Tox. 4 (85.4%)
• Skin Irrit. 2 (100%)
• Eye Dam. 1 (83.3%)
• Eye Irrit. 2A (16.7%)
• STOT SE 3 (97.9%)

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Disclaimer: Sold exclusively for laboratory research. Prohibited for commercial use, diagnostics, or human/animal applications. Buyers assume all compliance liability.