ChemicalBook Product Catalog Pharmaceutical intermediates Heterocyclic compound Pyridine compound Pyridine derivatives 2,6-Pyridinedicarboxaldehyde

2,6-Pyridinedicarboxaldehyde

Product Name2,6-Pyridinedicarboxaldehyde
CAS5431-44-7
MFC7H5NO2
MW135.12
EINECS226-589-6
MOL File5431-44-7.mol

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
Storage Class	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

Usage And Synthesis

Chemical Properties

White to gray solid

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

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.

Synthesis

Pyrrolidine,1,1'-(2,6-pyridinediyldicarbonyl)bis- (9CI)

69839-04-9

5431-44-7

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

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