| Identification | More | [Name]
2,6-Diacetylpyridine | [CAS]
1129-30-2 | [Synonyms]
1-(6-ACETYL-PYRIDIN-2-YL)-ETHANONE
2,6-DIACETYLPYRIDINE
pyridine-2,6-diacetyl
2,6-Diacetylpyridine 99%
2,6 Diacetylpyridine 99% min.
Ethanone, 1,1'-(2,6-pyridinediyl)bis-
2,6-Diacetylpyridine ,97%
1,1'-(2,6-Pyridinediyl)bisethanone
1,1'-(Pyridine-2,6-diyl)bisethanone | [EINECS(EC#)]
214-442-9 | [Molecular Formula]
C9H9NO2 | [MDL Number]
MFCD00006304 | [Molecular Weight]
163.17 | [MOL File]
1129-30-2.mol |
| Chemical Properties | Back Directory | [Appearance]
white to off-white crystalline needles or powder | [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. | [Detection Methods]
GC,NMR | [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 Data | Back Directory | [Hazard Codes ]
Xi,F | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R15:Contact with water liberates extremely flammable gases.
R10:Flammable. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S43:In case of fire, use ... (indicate in the space the precise type of fire-fighting equipment. If water increases the risk add-Never use water) .
S7/8:Keep container tightly closed and dry . | [WGK Germany ]
3
| [F ]
10 | [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29333990 |
| Hazard Information | Back Directory | [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 |
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