Description

4-Bromo-2-ethylpyridine (CAS No. 156761-88-5) is a high-purity brominated pyridine derivative with the molecular formula C₇H₈BrN. This heterocyclic compound features a bromine substituent at the 4-position and an ethyl group at the 2-position of the pyridine ring, making it a versatile intermediate for pharmaceutical, agrochemical, and materials science research. Its well-defined structure (IUPAC name: 4-bromo-2-ethylpyridine) ensures consistent reactivity in cross-coupling reactions, nucleophilic substitutions, and as a building block for complex molecular architectures. Available in >95% purity (GC), this compound is supplied in sealed amber vials under inert gas to ensure stability. Suitable for use in HPLC, LC-MS, and synthetic organic chemistry applications. Store at 2-8°C in a dry environment.

Properties

• CAS Number: 156761-88-5
• Complexity: 85
• IUPAC Name: 4-bromo-2-ethyl-pyridine
• InChI: InChI=1S/C7H8BrN/c1-2-7-5-6(8)3-4-9-7/h3-5H,2H2,1H3
• InChI Key: TVRGNBFSOZCSSE-UHFFFAOYSA-N
• Exact Mass: 184.98401
• Molecular Formula: C7H8BrN
• Molecular Weight: 186.05
• SMILES: CCC1=NC=CC(=C1)Br
• Topological: 12.9
• Monoisotopic Mass: 184.98401
• Synonyms: 4-Bromo-2-ethylpyridine, 156761-88-5, DTXSID60624685, DTXCID30575438, 868-499-5, Pyridine, 4-bromo-2-ethyl-, MFCD11223216, 4-Bromo-2-(ethyl-d3)pyridine, 4-Bromo-2-ethyl-pyridine, SCHEMBL539467, SCHEMBL25401107, SCHEMBL28214397, SCHEMBL28567815, TVRGNBFSOZCSSE-UHFFFAOYSA-N, GGA76188, AKOS006308519, AB63995, DS-6217, s10560, SY037354, DB-064140, CS-0035828, EN300-196675

Application

4-Bromo-2-ethylpyridine serves as a key precursor in the synthesis of biologically active compounds, particularly in the development of pharmaceuticals and crop protection agents. Its bromine moiety enables participation in palladium-catalyzed cross-coupling reactions (e.g., Suzuki, Heck) to construct bipyridines or functionalized pyridines. Researchers also utilize it to modify ligands for catalysis or as a scaffold in material science for designing organic electronic components. The ethyl group enhances lipophilicity, making it valuable in medicinal chemistry for probing structure-activity relationships.

Safety and Hazards

GHS Hazard Statements

• H226 (50%): Flammable liquid and vapor [Warning Flammable liquids]
• H302 (50%): Harmful if swallowed [Warning Acute toxicity, oral]
• H315 (50%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (50%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (50%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501

Hazard Classes and Categories

• Flam. Liq. 3 (50%)
• Acute Tox. 4 (50%)
• Skin Irrit. 2 (50%)
• Eye Irrit. 2A (50%)
• STOT SE 3 (50%)

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