2,6-Diacetylpyridine Chemical Properties

Melting point:

79-82 °C (lit.)

Boiling point:

126 °C / 6mmHg

Density 

1.2021 (rough estimate)

refractive index 

1.5300 (estimate)

storage temp. 

Inert atmosphere,Room Temperature

form 

Crystalline Needles or Powder

pka

0.88±0.10(Predicted)

color 

White to off-white

Water Solubility 

Soluble in water, chloroform, and DMSO.

BRN 

118286

InChI

InChI=1S/C9H9NO2/c1-6(11)8-4-3-5-9(10-8)7(2)12/h3-5H,1-2H3

InChIKey

BEZVGIHGZPLGBL-UHFFFAOYSA-N

SMILES

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

LogP

1.319 (est)

CAS DataBase Reference

1129-30-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,F

Risk Statements 

36/37/38-15-10

Safety Statements 

26-36-43-7/8

WGK Germany 

3

F 

10

HazardClass 

IRRITANT

HS Code 

29333990

Storage Class

11 - Combustible Solids

Hazard Classifications

Eye Irrit. 2
Skin Irrit. 2
STOT SE 3

MSDS

• Language:English Provider:2,6-Diacetylpyridine
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2,6-Diacetylpyridine Usage And Synthesis

Chemical Properties

white to off-white crystalline needles or powder

Uses

2,6-Diacetylpyridine is used as intermediate in organic synthesis. It is a precursor to ligands in coordination chemistry.

Application

2,6-Diacetylpyridine can be used as a starting material for the synthesis of:
Iron and cobalt bis(imino)pyridyl complexes, catalysts for ethylene oligomerization.
Thiosemicarbazone derivatives with potential application as anti-mycobacterial tuberculosis agent.
Macrocyclic pentadentate nitrogen–sulphur donor ligands by [1+1] condensation with 1,2-di(o-aminophenylthio)ethane.

Synthesis

The general procedure for the synthesis of 2,6-diacetylpyridine from 2,6-diethylpyridine was as follows: 1.0 equiv. of N-hydroxyphthalimide (NHPI) was added to a 25 mL Schlenk reaction tube and dried under vacuum for 15 min. Subsequently, acetonitrile was added as a solvent under oxygen atmosphere, followed by 2.0 equivalents of tert-butyl nitrite and 0.5 mmol of 2,6-diethylpyridine. After sealing the reaction tube with a polytetrafluoroethylene plug, it was immersed in an oil bath preheated to 90°C for 36 hours. After completion of the reaction, the solvent acetonitrile was removed by distillation under reduced pressure. The crude product was purified by column chromatography with the eluent being petroleum ether/ethyl acetate (5:1, v/v) to give 2,6-diacetylpyridine. The product was a yellow solid in 54% yield.

References

[1] Patent: CN107011133, 2017, A. Location in patent: Paragraph 0120; 0121; 0124; 0125
[2] Organic Letters, 2017, vol. 19, # 20, p. 5593 - 5596
[3] Patent: US9266982, 2016, B2. Location in patent: Page/Page column 34

2,6-Diacetylpyridine(1129-30-2)Related Product Information

• 2,5-PYRIDINEDICARBOXYLIC ACID
• Acetylferrocene
• DIPIPERIDINOMETHANE
• Acetylacetone
• N-ACETYL-L-TYROSINE ETHYL ESTER
• 3-Acetylpyridine
• 2-Acetylpyridine
• 2,6-Lutidine
• 4-Acetylpyridine
• Diethyl 1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate
• 4-Chloro-2,6-diacetylpyridine
• Pyridine
• 2,2',6,6'-TETRAYLTETRAACETYL-4,4'-BIPYRIDINE
• 2,6-Diacetyl-4-pyridinecarbonitrile
• 4-Methyl-2,6-diacetylpyridine
• 4-tert.-Butyl-2,6-diacetylpyridine
• 2,4-Diacetylpyridine
• 2,6-Diacetylpyridine