Description

2,6-Pyridinedicarbonyl dichloride (CAS No. 3739-94-4) is a highly reactive organic compound with the molecular formula C₇H₃Cl₂NO₂. This pyridine derivative is characterized by two carbonyl chloride functional groups positioned at the 2 and 6 locations on the pyridine ring, making it a valuable intermediate in organic synthesis and pharmaceutical research. The compound is typically supplied as a crystalline solid or powder, with high purity grades available for specialized applications. Its reactivity with nucleophiles such as amines and alcohols enables its use in the formation of amides, esters, and other functionalized pyridine derivatives. Proper handling under inert conditions is recommended due to its moisture sensitivity and potential for hydrolysis. Researchers and chemists will find this compound particularly useful for constructing complex heterocyclic frameworks and as a precursor for ligands in coordination chemistry.

Properties

• CAS Number: 3739-94-4
• Complexity: 188
• IUPAC Name: pyridine-2,6-dicarbonyl chloride
• InChI: InChI=1S/C7H3Cl2NO2/c8-6(11)4-2-1-3-5(10-4)7(9)12/h1-3H
• InChI Key: GWHOGODUVLQCEB-UHFFFAOYSA-N
• Exact Mass: 202.9540837
• Molecular Formula: C7H3Cl2NO2
• Molecular Weight: 204.01
• SMILES: C1=CC(=NC(=C1)C(=O)Cl)C(=O)Cl
• Topological: 47
• Monoisotopic Mass: 202.9540837
• Synonyms: 2,6-Pyridinedicarbonyl dichloride, Pyridine-2,6-dicarbonyl dichloride, EINECS 223-125-4, DTXSID70958483, DTXCID701386387, 223-125-4, gwhogoduvlqceb-uhfffaoysa-n, 3739-94-4, 2,6-Pyridinedicarbonyl chloride, 2,6-Pyridinedicarboxylic acid chloride, 2,6-Pyridinedicarboxylicacidchloride, pyridine-2,6-dicarbonyl chloride, MFCD00006289, Pyridine-2,6-dicarboxylic acid chloride, 2,6-Pyridinedicarbony chloride, SCHEMBL321127, 2,6-bis(chlorocarbonyl)pyridine, SCHEMBL11752479, 2,6-pyridine-dicarbonyl chloride, DAA73994, AKOS015891493, 2,6-Pyridinedicarbonyl dichloride, 97%, 2,6-Pyridinedicarboxylic acid dichloride, 2,6-pyridine dicarboxylic acid dichloride, SY075340, DB-049104, NS00046423, ST51037948, E78148, 2,6-Pyridinedicarbonyl chloride, Pyridine-2,6-dicarboxylic acid chloride

Application

2,6-Pyridinedicarbonyl dichloride serves as a versatile building block in the synthesis of pharmaceuticals, agrochemicals, and advanced materials. It is commonly employed in the preparation of pyridine-based ligands for metal-organic frameworks (MOFs) and catalysis. The compound’s dual acyl chloride functionality allows for efficient coupling with nucleophiles to form amide or ester linkages, making it valuable in peptide-mimetic and polymer chemistry. Additionally, it finds use in the development of fluorescent probes and bioactive molecules due to its rigid pyridine core.

Safety and Hazards

GHS Hazard Statements

• H314 (97.8%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]

Precautionary Statements

• P260, P264, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P363, P405, and P501

Hazard Classes and Categories

• Skin Corr. 1B (97.8%)

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