Description

2-Bromo-5-chloro-3-nitropyridine (CAS: 75806-86-9) is a high-purity heterocyclic compound with the molecular formula C₅H₂BrClN₂O₂, designed for advanced research and pharmaceutical applications. This halogenated nitropyridine derivative exhibits exceptional reactivity, making it a versatile intermediate in organic synthesis, particularly in the construction of complex nitrogen-containing scaffolds. With a molecular weight of 236.44 g/mol, it is supplied as a crystalline solid with ≥95% purity (HPLC), ensuring consistency for demanding synthetic protocols. Its unique bromo- and chloro-substitution pattern enables selective cross-coupling reactions, nucleophilic substitutions, and functional group transformations under controlled conditions. Ideal for medicinal chemistry, agrochemical development, and material science research, this compound is packaged under inert atmosphere to guarantee stability and longevity. Each batch undergoes rigorous QC analysis (NMR, LC-MS) to meet the stringent requirements of academic and industrial laboratories.

Properties

• CAS Number: 75806-86-9
• Complexity: 163
• IUPAC Name: 2-bromo-5-chloro-3-nitro-pyridine
• InChI: InChI=1S/C5H2BrClN2O2/c6-5-4(9(10)11)1-3(7)2-8-5/h1-2H
• InChI Key: VFMIDVIAQMFGGP-UHFFFAOYSA-N
• Exact Mass: 235.89882
• Molecular Formula: C5H2BrClN2O2
• Molecular Weight: 237.44
• SMILES: C1=C(C=NC(=C1[N+](=O)[O-])Br)Cl
• Topological: 58.7
• Monoisotopic Mass: 235.89882
• Synonyms: 2-Bromo-5-chloro-3-nitropyridine, DTXSID80299773, DTXCID60250908, 674-538-5, vfmidviaqmfggp-uhfffaoysa-n, 75806-86-9, 2-Bromo-3-nitro-5-chloropyridine, MFCD07368982, Pyridine, 2-bromo-5-chloro-3-nitro-, 2-bromo-5-chloro-3-nitro-pyridine, NSC132666, SCHEMBL126682, CHEMBL1997783, SBB054287, AKOS005255361, CS-W003387, GS-6897, NSC-132666, AC-27509, NCI60_000720, SY024682, 2-Bromo-5-chloro-3-nitropyridine, AldrichCPR, EN300-113419

2-Bromo-5-chloro-3-nitropyridine serves as a critical building block in the synthesis of pharmaceuticals, particularly for kinase inhibitors and antimicrobial agents. Its reactive halogen sites facilitate Suzuki-Miyaura and Buchwald-Hartwig couplings to construct biaryl motifs in drug candidates. Researchers utilize its nitro group for subsequent reductions to amines or cyclizations into fused heterocycles like imidazopyridines. The compound’s electron-deficient pyridine core also enables participation in nucleophilic aromatic substitution (S_NAr) reactions for diversifying molecular architectures.

Safety and Hazards

GHS Hazard Statements

• H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H318 (95%): Causes serious eye damage [Danger Serious eye damage/eye irritation]

Precautionary Statements

• P264, P264+P265, P270, P280, P301+P317, P302+P352, P305+P354+P338, P317, P321, P330, P332+P317, P362+P364, and P501

Hazard Classes and Categories

• Acute Tox. 4 (100%)
• Skin Irrit. 2 (100%)
• Eye Dam. 1 (95%)

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