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2,6-Diacetylpyridine

Product Name2,6-Diacetylpyridine
CAS1129-30-2
MFC9H9NO2
MW163.17
EINECS214-442-9
MOL File1129-30-2.mol

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

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

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

935-28-4

1129-30-2

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

Chemical Properties

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MSDS

Usage And Synthesis

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