3739-94-4

Basic information

• Product Name: 2,6-Pyridinedicarboxylic acid chloride
• Synonyms: PYRIDINE-2,6-DICARBONYL CHLORIDE;PYRIDINE-2,6-DICARBOXYLIC ACID CHLORIDE;2,6-PYRIDINEDICARBONYL DICHLORIDE;2,6-PYRIDINEDICARBOXYLIC ACID CHLORIDE;2,6-Pyridinedicarbonyl chloride;pyridine-2,6-dicarbonyl dichloride;2,6-Pyridinedicarboxylicacid dichloride;2,6-PYRIDINEDICARBOXYLIC ACID CHLORIDE 97%
• CAS NO: 3739-94-4
• Molecular Formula: C₇H₃Cl₂NO₂
• Molecular Weight: 204.01
• EINECS: 223-125-4
• Mol File: 3739-94-4.mol
• Article Data: 5

Chemical Properties

• Melting Point: 56-58 °C(lit.)
• Boiling Point: 284 °C(lit.)
• Flash Point: 284°C
• Appearance: White to brown/Crystalline Powder, Crystals or Chunks
• Density: 1.4521 (rough estimate)
• Vapor Pressure: 0.00292mmHg at 25°C
• Refractive Index: 1.6100 (estimate)
• PKA: -2.12±0.10(Predicted)
• Water Solubility: Insoluble in water.
• Sensitive: Moisture Sensitive
• BRN: 131556
• CAS DataBase Reference: 2,6-Pyridinedicarboxylic acid chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-Pyridinedicarboxylic acid chloride(3739-94-4)
• EPA Substance Registry System: 2,6-Pyridinedicarboxylic acid chloride(3739-94-4)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45-24/25
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• F: 10-19-21
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 3739-94-4(Hazardous Substances Data)

Usage

Description

2,6-Pyridinedicarboxylic acid chloride is an organic compound with the chemical formula C7H4Cl2NO2. It is a white to brown crystalline powder or crystals, known for its reactivity and versatility in chemical synthesis. 2,6-Pyridinedicarboxylic acid chloride is characterized by its two carboxylic acid groups at the 2nd and 6th positions of the pyridine ring and two chlorine atoms attached to the same positions, making it a valuable building block in the synthesis of various organic compounds.

Uses

Used in Chemical Synthesis:
2,6-Pyridinedicarboxylic acid chloride is used as a reagent for the synthesis of pyridine-based polyamido-polyester optically active macrocycles. It serves as a starting reagent during the synthesis of pyridine-bridged 2,6-bis-carboxamide Schiff's bases and is also used in the synthesis of N,N′-bis(1-pyrenylmethyl)pyridine-2,6-dicarboxamide.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,6-Pyridinedicarboxylic acid chloride is used as a starting material to synthesize various biologically active compounds. It is used to create pyridine-based polyamido-polyester optically active macrocycles by reacting with chiral diamine dihydrobromides. This application is crucial for the development of new drugs and therapeutic agents.
Used in Material Science:
2,6-Pyridinedicarboxylic acid chloride is also used in material science for the synthesis of novel materials with specific properties. For instance, it can be used to create pyridine-bridged 2,6-bis-carboxamide Schiff's bases by treating with L-alanine or 2-methyl-alanine methyl esters, which can be further utilized in the development of advanced materials with unique characteristics.
Used in Research and Development:
In the field of research and development, 2,6-Pyridinedicarboxylic acid chloride is employed as a key intermediate in the synthesis of various complex organic molecules. It is used in the synthesis of N,N′-bis(1-pyrenylmethyl)pyridine-2,6-dicarboxamide by reacting with 1-pyrenemethylamine hydrochloride in the presence of a base. 2,6-Pyridinedicarboxylic acid chloride can be further explored for its potential applications in various fields, including pharmaceuticals, materials science, and chemical engineering.

Synthesis

Pyridine-2,6-dicarboxylic acid (105 mg, 0.52 mmol) mixed with 7mL of thionyl chloride was heated to reflux for 3 hours. After the excess thionyl chloride was removed, a white solid was obtained and used for the following synthesis without further purifications.

InChI:InChI=1/C7H3Cl2NO2/c8-6(11)4-2-1-3-5(10-4)7(9)12/h1-3H

Upstream product

• 7170-36-7 6-(methoxycarbonyl)pyridine-2-carboxylic acid 
• 4663-97-2 pyridine-2,6-dicarboxylic acid diamide 
• 108-48-5 2,6-dimethylpyridine 

Downstream Products

• 5453-67-8 2,6-bis(methoxycarbonyl)pyridine 
• 15658-60-3 diethyl-2,6-pyridinedicarbonyl ester 
• 111584-10-2 N²,N⁶-dibenzylpyridine-2,6-dicarboxamide 
• 15658-59-0 pyridine-2,6-dihydroxamic acid 
• 5768-24-1 2,6-dibenzoylpyridine 
• 54945-23-2 6,12-dioxo-1,5,13,17,22-penta-azatricyclo-<15.2.2.1^7,11>docosa-7(22),8,10-triene 
• 145576-15-4 2,6-Bis<(2-oxocyclohexanyl)carbonyl>pyridine 
• 56173-26-3 2,6-pyridinedicarboxylic acid bis(p-nitrophenyl ester) 
• 151670-69-8 2,6-bis<(S)-4'-benzyloxazolin-2'-yl>pyridine 
• 128373-45-5 C₃₀H₂₈N₄O₆S 
• 129837-13-4 C₂₁H₁₅N₃O₄ 
• 94136-74-0 N,N'-bis<3-propyl>-2,6-pyridinedicarbamide 
• 94136-59-1 N,N'-bis<5-pentyl>-2,6-pyridinedicarbamide 
• 344344-54-3 (R,S)-5,13-diphenyl-3,6,9,12,15-pentaoxa-21-azabicyclo<15.3.1>heneicosa-1(21),17,19-triene-2,16-dione 

Relevant articles and documents

-

-

Calix[6]arene-picolinamide extractants for radioactive waste treatment: Effect of additional carboxy binding Sites in the pyridine 6-positions on complexation, extraction efficiency and An/Ln separation

The effect of the presence of an additional ester or amide carboxy group in the 6-position of the pyridine nuclei of calixarene-based picolinamide ligands on the extraction and complexation properties of lanthanide(III) and actinide(III) metal ions was studied. For this purpose, six new ligands 1-6 were synthesized; their conformational properties were studied both in solution and in the solid state, and their binding properties towards lanthanide (Ln III) and actinide (AnIII) metal ions were determined under extracting conditions simulating those present in radioactive waste. In the presence of BrCosan as synergizer, a rather high efficiency in the extraction of trivalent metal ions by these ligands was observed even at [HNO3] > 2-3 M. Complexation of LnIII metal ions was also studied under homogeneous conditions (methanol solution), both in chloride and nitrate media, by using spectrophotometry and calorimetry. A comparison with the data obtained with ligands L1-L3, lacking the additional binding sites in the 6-position of the pyridine nuclei, is reported and the effects of the structure of the ligands on the stoichiometry of the complexes, coordination of the metal ions, basicity of the pyridine binding groups and efficiency and selectivity in the extractions are also discussed.

Chelate bis(imino)pyridine cobalt complexes: Synthesis, reduction, and evidence for the generation of ethene polymerization catalysts by Li+ cation activation

Treatment of the bis(iminobenzyl)pyridine chelate Schiff-base ligand 8 (ligPh) with FeCl2 or CoCl2 yielded the corresponding (ligPh)MCl2 complexes 9 (Fe) and 10 (Co). The reaction of 10 with methyllithium or "butadiene-magnesium" resulted in reduction to give the corresponding (ligPh)Co(I)Cl product 11. Similarly, the bis(aryliminoethyl)pyridine ligand (ligMe) was reacted with CoCl2 to yield (ligMe)CoCl2 (12). Reduction to (ligMe)CoCl (13) was effected by treatment with "butadiene-magnesium". Complex 13 reacted with Li[B(C 6F5)4] in toluene followed by treatment with pyridine to yield [(ligMe)Co+-pyridine] (15). The reaction of the Co(II) complexes 10 or 12 with ca. 3 molar equiv of methyllithium gave the cobalt(I) complexes 16 and 17, respectively. Treatment of the (lig Me)CoCH3 (17) with Li[B(C6F5) 4] gave a low activity ethene polymerization catalyst. Likewise, complex 16 produced polyethylene (activity = 33 g(PE) mmol(cat)-1 h-1 bar-1 at room temperature) upon treatment with a stoichiometric amount of Li[B(C6F5)4]. A third ligand (ligOMe) was synthesized featuring methoxy groups in the ligand backbone (22). Coordination to FeCl2 and CoCl2 yielded the desired compounds 23 and 24. Reaction with MeLi gave (lig OMe)CoMe (25/26). Treatment of 25/26 with excess B(C 6F5)3 gave the η6-arene cation complex 27, where one Co-N linkage was cleaved. Activation of 25/26 with Li[B(C6F5)4] again gave a catalytically active species.