ChemicalBook--->CAS DataBase List--->33279-01-5

33279-01-5

33279-01-5 Structure

33279-01-5 Structure
IdentificationBack 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 PropertiesBack 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
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Danger
[Hazard statements ]

H302-H312-H315-H319-H332
[Precautionary statements ]

P261-P280-P301+P312a-P304+P340-P305+P351+P338-P501a
[Hazard Codes ]

T
[RIDADR ]

UN3276
[HazardClass ]

6.1
[PackingGroup ]

III
[HS Code ]

2933599590
Hazard InformationBack 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]

Ethyl propionate

105-37-3

3-OXO-PENTANENITRILE

33279-01-5

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
Spectrum DetailBack Directory
[Spectrum Detail]

3-OXO-PENTANENITRILE(33279-01-5)1HNMR
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