Description
6-Bromo-2-chloro-3-iodopyridine (CAS No. 1138444-17-3) is a high-purity halogenated pyridine derivative with the molecular formula C5H2BrClIN. This compound is a versatile building block in organic synthesis, particularly in pharmaceutical and agrochemical research. Its unique structure, featuring bromo, chloro, and iodo substituents on the pyridine ring, enables selective functionalization for the development of complex heterocyclic compounds. The product is supplied as a crystalline solid with ≥95% purity (HPLC), ensuring optimal performance in cross-coupling reactions, nucleophilic substitutions, and metal-catalyzed transformations. Proper storage under inert conditions at 2-8°C is recommended to maintain stability.
Properties
- CAS Number: 1138444-17-3
- Complexity: 103
- IUPAC Name: 6-bromo-2-chloro-3-iodo-pyridine
- InChI: InChI=1S/C5H2BrClIN/c6-4-2-1-3(8)5(7)9-4/h1-2H
- InChI Key: LZDHGMJHIXUOIF-UHFFFAOYSA-N
- Exact Mass: 316.81039
- Molecular Formula: C5H2BrClIN
- Molecular Weight: 318.34
- SMILES: C1=CC(=NC(=C1I)Cl)Br
- Topological: 12.9
- Monoisotopic Mass: 316.81039
- Synonyms: 6-Bromo-2-chloro-3-iodopyridine, 1138444-17-3, DTXSID60673870, DTXCID50624619, 690-042-1, Pyridine, 6-bromo-2-chloro-3-iodo-, MFCD11857690, SCHEMBL15940548, LZDHGMJHIXUOIF-UHFFFAOYSA-N, AKOS015835364, CS-W003811, DS-16913, SY031486, DB-060558, 6-Bromo-2-chloro-3-iodopyridine, AldrichCPR, EN300-1083993
Application
6-Bromo-2-chloro-3-iodopyridine serves as a key intermediate in medicinal chemistry for the synthesis of kinase inhibitors and other bioactive molecules. Its multiple halogen sites allow sequential functionalization via Suzuki-Miyaura, Buchwald-Hartwig, or Ullmann coupling reactions. Researchers utilize this compound in the development of PET radiotracers due to the iodine moiety’s potential for radioisotope incorporation. The electron-deficient pyridine core also makes it valuable for materials science applications in organic electronics.
Safety and Hazards
GHS Hazard Statements
- H301 (66.7%): Toxic if swallowed [Danger Acute toxicity, oral]
- H315 (66.7%): Causes skin irritation [Warning Skin corrosion/irritation]
- H319 (66.7%): 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, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501
Hazard Classes and Categories
- Acute Tox. 3 (66.7%)
- Skin Irrit. 2 (66.7%)
- Eye Irrit. 2A (66.7%)
- STOT SE 3 (66.7%)
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