2,6-Pyridinedicarboxaldehyde Chemical Properties

Melting point:

124-125 °C (lit.)

Boiling point:

152-154 °C/103 mmHg (lit.)

Density 

1.3124 (rough estimate)

refractive index 

1.5800 (estimate)

storage temp. 

2-8°C

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Powder

pka

1.84±0.10(Predicted)

color 

White to tan

InChI

InChI=1S/C7H5NO2/c9-4-6-2-1-3-7(5-10)8-6/h1-5H

InChIKey

PMWXGSWIOOVHEQ-UHFFFAOYSA-N

SMILES

C1(C=O)=NC(C=O)=CC=C1

CAS DataBase Reference

5431-44-7(CAS DataBase Reference)

NIST Chemistry Reference

2,6-Pyridinedicarboxaldehyde(5431-44-7)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39-37/39

WGK Germany 

3

HS Code 

29333990

2,6-Pyridinedicarboxaldehyde Usage And Synthesis

Chemical Properties

White to gray solid

Uses

2,6-Pyridinedicarboxaldehyde is an intermediate used to prepare functionalized resin Amberlite XAD-4,?boron-dipyrromethene (BODIPY)-based fluorescence probe with a N,N′-(pyridine-2, 6-diylbis(methylene))-dianiline substituent and novel N-heterocyclic chitosan aerogel derivatives.

Uses

2,6-Pyridinedicarboxaldehyde has been used in preparation of:

• functionalized resin Amberlite XAD-4
• boron-dipyrromethene (BODIPY)-based fluorescence probe with a N,N′-(pyridine-2, 6-diylbis(methylene))-dianiline substituent
• novel N-heterocyclic chitosan aerogel derivatives

Synthesis

General procedure for the synthesis of 2,6-pyridinedicarboxaldehyde from the compound (CAS: 69839-04-9): to a stirring LiAlH4 solution (0.31 g, 8.24 mmol; dissolved in 3 mL of anhydrous THF) at 0 °C, slowly add dropwise 2,6-bis(1-pyrrolidinocarbonyl)pyridine (3.0 g, 11 mmol) to anhydrous THF ( 20 mL) solution. The reaction mixture was stirred in 30 mL of anhydrous THF for 16 h. After 40 min, the reaction mixture was carefully hydrolyzed with 2 M aqueous hydrochloric acid. The organic phase was separated and the aqueous phase was extracted with CH2Cl2 (5 x 10 mL). The organic phase was combined and dried with Na2SO4. The solvent was removed in vacuum and the product was recrystallized by ether to give an almost colorless powdered 2,6-pyridinedicarboxaldehyde. The yield was 1.30 g (76% yield).

References

[1] Tetrahedron Letters, 2013, vol. 54, # 3, p. 217 - 219

2,6-Pyridinedicarboxaldehyde(5431-44-7)Related Product Information

• 2,5-PYRIDINEDICARBOXYLIC ACID
• DIPIPERIDINOMETHANE
• 2,6-Lutidine
• Pyridine-2,6-dicarbohydrazide
• Pyridine
• PYRIDINE-2,4-DICARBONITRILE
• PYRIDINE-2,3-DICARBONITRILE
• 3,5-DIAMINOPYRIDINE
• 3-Pyridylboronic acid
• 2,6-Pyridinedimethanol
• Diethyl 1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate
• 2,6-Pyridinedicarboxylic acid monomethyl ester
• Dimethyl 2,6-Pyridinedicarboxylate
• Pyridine-2,6-dicarboxylic acid
• Chelidamic acid
• Pyrroloquinoline quinone
• 2 2'-BIPYRIDINE-4 4'-DICARBOXALDEHYDE
• 2,6-Pyridinedicarboxylic acid chloride