Description

Methyl 5-bromopyridine-2-carboxylate (CAS No. 29682-15-3) 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 5-position and an ester group at the 2-position, enabling diverse functionalization via cross-coupling reactions, nucleophilic substitutions, or hydrolysis. Supplied as a white to off-white crystalline solid with ≥95% purity (HPLC), it is ideal for precision applications. Packaged under inert gas to ensure stability, this reagent is compatible with anhydrous conditions and sensitive synthetic protocols. Store in a cool, dry place away from light and moisture to maintain optimal performance.

Properties

• CAS Number: 29682-15-3
• Complexity: 151
• IUPAC Name: methyl 5-bromopyridine-2-carboxylate
• InChI: InChI=1S/C7H6BrNO2/c1-11-7(10)6-3-2-5(8)4-9-6/h2-4H,1H3
• InChI Key: JEURNBCYNWNADN-UHFFFAOYSA-N
• Exact Mass: 214.95819
• Molecular Formula: C7H6BrNO2
• Molecular Weight: 216.03
• SMILES: COC(=O)C1=NC=C(C=C1)Br
• Topological: 39.2
• Monoisotopic Mass: 214.95819
• Synonyms: Methyl 5-bromopyridine-2-carboxylate, 2-Pyridinecarboxylic acid, 5-bromo-, methyl ester, 681-695-3, 29682-15-3, methyl 5-bromopicolinate, 5-Bromopyridine-2-carboxylic acid methyl ester, MFCD04112493, METHYL 5-BROMO-2-PYRIDINECARBOXYLATE, 5-bromo-pyridine-2-carboxylic acid methyl ester, methyl5-bromopicolinate, 5-bromo-2-pyridinecarboxylic acid methyl ester, SCHEMBL109364, CHEMBL4071031, JEURNBCYNWNADN-UHFFFAOYSA-, DTXSID20426844, JEURNBCYNWNADN-UHFFFAOYSA-N, 5-Bromopicolinic Acid Methyl Ester, BCP27507, CS-D0954, BBL101015, Methyl-5-bromopyridine-2-carboxylate, SBB053856, STL554809, AKOS005256535, methyl 5-bromo-pyridine-2-carboxylate, methyl-5-bromo-2-pyridine carboxylate, AC-1436, FS-2153, PB29312, HY-32778, SY009344, DB-013123, M2614, ST50408672, EN300-127280, methyl 5-bromopyridine-2-carboxylate, AldrichCPR, AC-907/34105003, Z1065600802, InChI=1/C7H6BrNO2/c1-11-7(10)6-3-2-5(8)4-9-6/h2-4H,1H3

Application

Methyl 5-bromopyridine-2-carboxylate serves as a key intermediate in the synthesis of active pharmaceutical ingredients (APIs) and ligands for catalysis. It is widely used in Suzuki-Miyaura and Buchwald-Hartwig coupling reactions to construct complex heterocyclic scaffolds. Researchers also employ it in the development of kinase inhibitors and other bioactive molecules due to its modular reactivity. Its ester group allows further derivatization to carboxylic acids or amides, expanding its utility in medicinal chemistry.

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 (88.9%): 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. 2A (100%)
• STOT SE 3 (88.9%)

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