Description
Methyl 3-bromo-2-pyridinecarboxylate (CAS No. 53636-56-9) is a high-purity brominated pyridine derivative with the molecular formula C7H6BrNO2. This compound, also known as methyl 3-bromopicolinate, is a versatile building block in organic synthesis and pharmaceutical research. Its structure features a reactive bromine atom at the 3-position and an ester group at the 2-position of the pyridine ring, enabling diverse functionalization. Supplied as a crystalline solid with ≥95% purity (HPLC), it is ideal for coupling reactions, heterocycle synthesis, and ligand preparation. Packaged under inert gas to ensure stability, this reagent is suitable for use in medicinal chemistry, agrochemical development, and material science applications. Store in a cool, dry place away from light and moisture.
Properties
- CAS Number: 53636-56-9
- Complexity: 151
- IUPAC Name: methyl 3-bromopyridine-2-carboxylate
- InChI: InChI=1S/C7H6BrNO2/c1-11-7(10)6-5(8)3-2-4-9-6/h2-4H,1H3
- InChI Key: GSTYLUGZSCVBTJ-UHFFFAOYSA-N
- Exact Mass: 214.95819
- Molecular Formula: C7H6BrNO2
- Molecular Weight: 216.03
- SMILES: COC(=O)C1=C(C=CC=N1)Br
- Topological: 39.2
- Monoisotopic Mass: 214.95819
- Synonyms: Methyl 3-bromo-2-pyridinecarboxylate, 814-519-2, Methyl 3-Bromopicolinate, 53636-56-9, Methyl 3-bromopyridine-2-carboxylate, MFCD12025946, 3-bromopyridine-2-carboxylic acid methyl ester, 3-BROMOPYRIDINE-2-CARBOXYLICACIDMETHYLESTER, 2-Pyridinecarboxylic acid, 3-bromo-, methyl ester, 3-Bromo-2-(methoxycarbonyl)pyridine, SCHEMBL394073, DTXSID50510922, GSTYLUGZSCVBTJ-UHFFFAOYSA-N, methyl3-bromo-2-pyridinecarboxylate, BBL101196, CL0157, SBB095195, STL554992, AKOS005073696, methyl 3-bromo-pyridine-2-carboxylate, AC-7316, CS-W001191, PB13499, SS-3013, SY005700, DB-018103, 3-Bromopyridine-2-carboxylic acid methy ester, EN300-122161, 3-Bromo-2-pyridine carboxylic acid methyl ester, AC-907/34105002, 3-BROMO-PYRIDINE-2-CARBOXYLIC ACID METHYL ESTER
Application
Methyl 3-bromo-2-pyridinecarboxylate serves as a key intermediate in Suzuki-Miyaura and Stille cross-coupling reactions for constructing biaryl systems. It is widely used in pharmaceutical research for the synthesis of kinase inhibitors and other nitrogen-containing heterocycles. The compound’s ester group allows further derivatization via hydrolysis or amidation, making it valuable for drug discovery pipelines.
Safety and Hazards
GHS Hazard Statements
- H302 (66.7%): Harmful if swallowed [Warning Acute toxicity, oral]
- H312 (33.3%): Harmful in contact with skin [Warning Acute toxicity, dermal]
- H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
- H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
- H332 (33.3%): Harmful if inhaled [Warning Acute toxicity, inhalation]
- H335 (100%): 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, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501
Hazard Classes and Categories
- Acute Tox. 4 (66.7%)
- Acute Tox. 4 (33.3%)
- Skin Irrit. 2 (100%)
- Eye Irrit. 2A (100%)
- Acute Tox. 4 (33.3%)
- STOT SE 3 (100%)
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