2,6-Pyridinedicarboxylic acid chloride
[CAS# 3739-94-4]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Pyridine derivative
• Name: 2,6-Pyridinedicarboxylic acid chloride
• Synonyms: 2,6-Pyridinedicarbonyl dichloride; Pyridine-2,6-dicarboxylic acid chloride
• Molecular Formula: C₇H₃Cl₂NO₂
• Molecular Weight: 204.01
• CAS Registry Number: 3739-94-4
• EC Number: 223-125-4
• SMILES: C1=CC(=NC(=C1)C(=O)Cl)C(=O)Cl

Properties

• Melting point: 57-61 °C
• Boiling point: 284 °C

Safety Data

• Hazard Symbols: GHS05 Danger
• Risk Statements: H314
• Safety Statements: P260-P264-P280-P301+P330+P331-P302+P361+P354-P304+P340-P305+P354+P338-P316-P321-P363-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin corrosion	Skin Corr.	1B	H314

• Transport Information: UN 3261

Discovery and Applications

2,6-Pyridinedicarbonyl chloride, also known as dipyridinyl chloride or 2,6-pyridinedicarbonyl chloride, has the chemical formula C₇H₃Cl₂NO₂ and a molecular weight of 204.01 g/mol. The pyridine ring of this compound is substituted with carbonyl chloride groups at the 2 and 6 positions to become a reactive acyl chloride derivative of pyridinedicarboxylic acid. It plays an important role in organic synthesis and materials science due to its reactivity and versatile functional groups.

2,6-Pyridinedicarbonyl chloride originated from the study of acyl chlorides and their applications in organic synthesis. The development of this compound stemmed from the need for an effective reagent to introduce acyl groups into a variety of molecules. Researchers recognized its potential in the synthesis of versatile compounds and advanced materials. The synthesis usually involves the chlorination of 2,6-pyridinedicarboxylic acid to convert it into a reactive chloride derivative. The synthesis of 2,6-pyridinedicarboxylic acid chloride involves the conversion of 2,6-pyridinedicarboxylic acid into its acid chloride form using reagents such as thionyl chloride (SOCl₂) or phosphorus trichloride (PCl₃). The reaction is usually carried out under controlled conditions to obtain the desired product. The compound produced by this synthesis is highly reactive and can be used in a variety of chemical transformations.

In organic synthesis, 2,6-pyridinedicarboxylic acid chloride can be used as a versatile acylating agent. Its two acid chloride groups enable it to introduce acyl functionalities into different molecules, facilitating the synthesis of multifunctional compounds including esters, amides, and anhydrides. This reactivity is essential for the creation of complex organic molecules in pharmaceuticals and fine chemicals.

The compound is used in polymer chemistry to synthesize polyimides and polyesters. Its ability to react with diols or diamines enables it to form polymers with a pyridine backbone, which helps improve the thermal stability and mechanical properties of the material. These polymers can be used in high-performance materials and coatings.

2,6-Pyridinedicarboxylic acid chloride is also used in coordination chemistry to synthesize metal organic frameworks (MOFs) and coordination polymers. Its bifunctional nature enables it to coordinate with metal ions to form structures with potential applications in catalysis, gas storage, and separation technologies.

In research laboratories, it acts as a reagent to explore new synthetic pathways and develop novel compounds. Its reactivity with nucleophiles makes it a valuable tool for studying acylation reactions and designing new molecules with specific functionalities.

References

2023. Thiocyanate-induced N-activation and nucleophilic 1,2-dearomatization of pyridinedicarbonyl dichloride: a synthetic route to a novel 1,2-dihydropyridine-based heterocyclic compound. Journal of the Iranian Chemical Society, 20(8).
DOI: 10.1007/s13738-023-02863-1

2020. Synthesis of Macroheterocycles Containing Pyridine-2,6-dicarboxylic and Adipic Acid Ester and Hydrazide Fragments Starting from Tetrahydropyran. Russian Journal of Organic Chemistry, 56(12).
DOI: 10.1134/s1070428020120295

2019. Synthesis and Enzyme Inhibitory Activity of Novel Pyridine-2,6-dicarboxamides Bearing Primary Sulfonamide Groups. Russian Journal of Organic Chemistry, 55(12).
DOI: 10.1134/s1070428019120248