Identification | Back Directory | [Name]
3-OXO-PENTANENITRILE | [CAS]
33279-01-5 | [Synonyms]
3-OXOPENTANONITRILE 3-OXO-PENTANENITRILE Propionylacetonitrile Pentanenitrile, 3-oxo- cyanoMethyl ethyl ketone Propanoylacetonitrile, 1-Cyanobutan-2-one | [Molecular Formula]
C5H7NO | [MDL Number]
MFCD07367087 | [MOL File]
33279-01-5.mol | [Molecular Weight]
97.12 |
Chemical Properties | Back Directory | [Boiling point ]
30°C | [density ]
0.956±0.06 g/cm3(Predicted) | [storage temp. ]
Inert atmosphere,Room Temperature | [pka]
10.37±0.10(Predicted) | [Appearance]
White to off-white Solid |
Hazard Information | Back Directory | [Uses]
A facile procedure for the high-yielding acylation of nitrile anions with unactivated esters to provide β-?keto nitriles (Propionylacetonitrile) is reported. | [Synthesis]
The general procedure for the synthesis of 3-oxopentanenitrile from ethyl propionate is as follows:
- Acetonitrile (1.17 mL) was slowly added dropwise to a stirred n-butyllithium solution (1.6 M hexane solution, 14.06 mL) at -78 °C and stirred at this temperature for 1 hour.
- Subsequently, ethyl propionate (1.5 mL) was added dropwise and the reaction mixture was slowly warmed to -45 °C, at which temperature stirring was continued for 2 hours.
- Upon completion of the reaction, the mixture was acidified to pH 2 with aqueous 2N hydrochloric acid and then concentrated by evaporation.
- The residue was extracted with dichloromethane and the combined organic phases were dried over magnesium sulfate, followed by evaporation of the solvent.
- 3-Oxopentanenitrile was finally obtained in 80% yield.
1H NMR (CDCl3) δ: 1.14 (t, 3H), 2.66 (q, 2H), 3.46 (s, 2H). | [References]
[1] Patent: WO2007/99326, 2007, A1. Location in patent: Page/Page column 114 [2] Patent: WO2007/99335, 2007, A1. Location in patent: Page/Page column 96 [3] Patent: WO2007/99317, 2007, A1. Location in patent: Page/Page column 105 [4] Patent: US2002/32184, 2002, A1 [5] Patent: US2008/45496, 2008, A1. Location in patent: Page/Page column 15 |
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