Description
2,3-Dibromo-5-chloropyridine (CAS No. 137628-17-2) is a high-purity halogenated pyridine derivative with the molecular formula C5H2Br2ClN. This compound is a versatile building block in organic synthesis, particularly in pharmaceutical and agrochemical research. Its unique structure, featuring bromine and chlorine substituents on the pyridine ring, enables selective functionalization for the development of complex heterocyclic compounds. Suitable for cross-coupling reactions, nucleophilic substitutions, and metal-catalyzed transformations, this reagent is supplied as a crystalline solid with ≥95% purity (HPLC). Store in a cool, dry place under inert conditions to ensure stability. Ideal for researchers seeking to explore novel pyridine-based scaffolds.
Properties
- CAS Number: 137628-17-2
- Complexity: 101
- IUPAC Name: 2,3-dibromo-5-chloro-pyridine
- InChI: InChI=1S/C5H2Br2ClN/c6-4-1-3(8)2-9-5(4)7/h1-2H
- InChI Key: GDUFWKJMOOVEMX-UHFFFAOYSA-N
- Exact Mass: 270.82220
- Molecular Formula: C5H2Br2ClN
- Molecular Weight: 271.34
- SMILES: C1=C(C=NC(=C1Br)Br)Cl
- Topological: 12.9
- Monoisotopic Mass: 268.82425
- Synonyms: 2,3-Dibromo-5-chloropyridine, 137628-17-2, DTXSID40451411, DTXCID30402230, 805-817-3, 5-CHLORO-2,3-DIBROMOPYRIDINE, Pyridine, 2,3-dibromo-5-chloro-, 2,3 DIBROMO-5-CHLORO PYRIDINE, MFCD08687254, 2,3-dibromo-5-chloro-pyridine, 2,3-Dibromo-5-dichloropyridine, SCHEMBL3361574, GDUFWKJMOOVEMX-UHFFFAOYSA-N, BBL101818, SBB054253, STL555615, AKOS007930302, AC-6263, CS-W003541, GS-5030, PB40468, SY019255, DB-027518, D4381, EN300-157894
Application
2,3-Dibromo-5-chloropyridine serves as a key intermediate in the synthesis of active pharmaceutical ingredients (APIs) and specialty chemicals. It is widely used in Suzuki-Miyaura and Stille cross-coupling reactions to introduce pyridine motifs into drug candidates. Researchers also employ it in the development of herbicides and fungicides due to its bioactive halogenated structure. Its reactivity makes it valuable for constructing ligands in catalysis and materials science.
Safety and Hazards
GHS Hazard Statements
- H301 (20%): Toxic if swallowed [Danger Acute toxicity, oral]
- H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
- H318 (20%): Causes serious eye damage [Danger Serious eye damage/eye irritation]
- H319 (80%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
- H335 (60%): 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, P305+P354+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501
Hazard Classes and Categories
- Acute Tox. 3 (20%)
- Skin Irrit. 2 (100%)
- Eye Dam. 1 (20%)
- Eye Irrit. 2 (80%)
- STOT SE 3 (60%)
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