Description

5-Bromo-6-methylpyridin-2-amine (CAS No. 42753-71-9) is a high-purity heterocyclic organic compound with the molecular formula C₆H₇BrN₂. This brominated pyridine derivative is a valuable building block in pharmaceutical and agrochemical research, particularly in the synthesis of complex molecules. Its unique structure, featuring an amine group at the 2-position and a bromo-methyl substitution pattern, makes it a versatile intermediate for cross-coupling reactions, nucleophilic substitutions, and metal-catalyzed transformations. Supplied as an off-white to light brown crystalline powder, it is characterized by excellent batch-to-batch consistency with ≥95% purity (HPLC). Proper storage at 2-8°C under inert atmosphere ensures long-term stability. This product is ideal for medicinal chemistry, material science, and as a precursor for ligand development in catalysis research.

Properties

• CAS Number: 42753-71-9
• Complexity: 97.1
• IUPAC Name: 5-bromo-6-methyl-pyridin-2-amine
• InChI: InChI=1S/C6H7BrN2/c1-4-5(7)2-3-6(8)9-4/h2-3H,1H3,(H2,8,9)
• InChI Key: SEOZHXRTVJPQPZ-UHFFFAOYSA-N
• Exact Mass: 185.97926
• Molecular Formula: C6H7BrN2
• Molecular Weight: 187.04
• SMILES: CC1=C(C=CC(=N1)N)Br
• Topological: 38.9
• Monoisotopic Mass: 185.97926
• Synonyms: 42753-71-9, 5-Bromo-6-methylpyridin-2-amine, 5-Bromo-6-methyl-2-pyridinamine, 2-Pyridinamine, 5-bromo-6-methyl-, EINECS 255-927-5, DTXSID8068414, SEOZHXRTVJPQPZ-UHFFFAOYSA-, DTXCID7040154, 255-927-5, inchi=1/c6h7brn2/c1-4-5(7)2-3-6(8)9-4/h2-3h,1h3,(h2,8,9), 2-Amino-5-bromo-6-methylpyridine, 6-Amino-3-bromo-2-methylpyridine, 6-Amino-3-bromo-2-picoline, MFCD00068230, 2-amino-5-bromo-6-picoline, 5-bromo-6-methylpyridin-2-ylamine, EN300-91286, 5-bromo-6-methyl-2-pyridylamine, 5-bromo-6-methyl-pyridin-2-amine, 4JO, 5-bromo-6-methyl-pyridin-2-ylamine, AC-907/30003055, SCHEMBL117968, DU7SD24F59, 3-bromo-2-methyl-6-aminopyridine, BDBM626228, 6-amino-3-bromo-2-methyl-pyridine, BCP22089, 5-BROMO-2-AMINO-6-PICOLINE, SBB000260, STK802993, AKOS000268954, AB02783, AC-2958, CS-W007550, FS-1036, 6-Amino-3-bromo-2-methylpyridine, 97%, SY003423, A1889, NS00031232, ST50214562, Q27454754, Z57376600, F8881-6528, 6-Amino-3-bromo-2-picoline (6-Amino-3-bromo-2-methylpyridine)

Application

5-Bromo-6-methylpyridin-2-amine serves as a key intermediate in the synthesis of pharmaceutical compounds, particularly for developing kinase inhibitors and antimicrobial agents. Its reactive bromo group enables efficient Suzuki-Miyaura and Buchwald-Hartwig coupling reactions for constructing biaryl systems. Researchers utilize this compound in structural-activity relationship (SAR) studies due to its ability to introduce both hydrogen-bond donor (amine) and hydrophobic (bromo-methyl) motifs. The methyl group adjacent to the bromine atom provides steric influence that can direct regioselective transformations.

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 (98%): 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. 2 (100%)
• STOT SE 3 (98%)

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