Description

Methyl 6-bromopyridine-2-carboxylate (CAS No. 26218-75-7) is a high-purity brominated pyridine derivative with the molecular formula C₇H₆BrNO₂. This compound is a versatile building block in organic synthesis, particularly in pharmaceutical and agrochemical research. Its structure features a reactive bromine substituent at the 6-position and an ester group at the 2-position, enabling further functionalization via cross-coupling reactions, nucleophilic substitutions, or hydrolysis. Ideal for Suzuki, Stille, or Buchwald-Hartwig couplings, this reagent is supplied as a crystalline solid with ≥95% purity (HPLC). Store under inert conditions at 2-8°C to ensure stability. Suitable for use in medicinal chemistry, material science, and as a precursor for heterocyclic scaffolds.

Properties

• CAS Number: 26218-75-7
• Complexity: 151
• IUPAC Name: methyl 6-bromopyridine-2-carboxylate
• InChI: InChI=1S/C7H6BrNO2/c1-11-7(10)5-3-2-4-6(8)9-5/h2-4H,1H3
• InChI Key: SGNCOKUHMXLGAH-UHFFFAOYSA-N
• Exact Mass: 214.95819
• Molecular Formula: C7H6BrNO2
• Molecular Weight: 216.03
• SMILES: COC(=O)C1=NC(=CC=C1)Br
• Topological: 39.2
• Monoisotopic Mass: 214.95819
• Synonyms: 26218-75-7, Methyl 6-bromopyridine-2-carboxylate, Methyl 6-bromo-2-pyridinecarboxylate, DTXSID50584623, DTXCID60535388, 627-687-5, Methyl 6-bromopicolinate, 6-Bromopyridine-2-carboxylic Acid Methyl Ester, 6-Bromopicolinic acid methyl ester, 2-PYRIDINECARBOXYLIC ACID, 6-BROMO-, METHYL ESTER, Methyl-6-bromopyridine-2-carboxylate, MFCD06203934, Methyl6-bromopicolinate, Methyl-6-Bromo-2-Pyridine Carboxylate, 2-BROMO-6-NICOTINIC ACID METHYL ESTER, methyl-6-bromopicolinate, SCHEMBL38206, SGNCOKUHMXLGAH-UHFFFAOYSA-N, BCP21665, CS-M1028, STR07106, Methyl 6-BroMoyridine-2-carboxylate, methyl 2-bromopyridine-6-carboxylate, SBB065221, AKOS000279089, methyl 6-bromo-pyridine-2-carboxylate, methyl-6-bromo-pyridine-2-carboxylate, AB23211, FB55586, PS-4896, AC-24955, HY-76562, SY009096, DB-030946, Methyl-6-bromopyridine-2-carboxylate, 97%, M2342, EN300-154662, 6-bromo-pyridine-2-carboxylic acid methyl ester, Z1269143200, Methyl 6-bromopicolinate;6-Bromopyridine-2-carboxylic acid methyl ester, 6-Bromopyridine-2-carboxylic Acid Methyl Ester;6-Bromopicolinic acid methyl ester

Application

Methyl 6-bromopyridine-2-carboxylate is widely used as a key intermediate in the synthesis of active pharmaceutical ingredients (APIs) and ligands for catalysis. Its bromine moiety facilitates palladium-catalyzed cross-coupling reactions to construct complex pyridine-based architectures. Researchers employ it in the development of kinase inhibitors, receptor modulators, and agrochemicals. The ester group allows straightforward conversion to carboxylic acids or amides, expanding its utility in drug discovery.

Safety and Hazards

GHS Hazard Statements

• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H318 (95.5%): Causes serious eye damage [Danger Serious eye damage/eye irritation]
• H335 (97.7%): 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+P354+P338, P317, P319, P321, P332+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Skin Irrit. 2 (100%)
• Eye Dam. 1 (95.5%)
• STOT SE 3 (97.7%)

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