3-Oxo-cyclopentanecarbonitrile Chemical Properties

Boiling point:

250-270 °C(Press: 1 Torr)

Density 

1.08±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

Safety Information

HS Code 

2926907090

3-Oxo-cyclopentanecarbonitrile Usage And Synthesis

Uses

3-Cyanocyclopentanone is used for catalytic enantioselective conjugate addition of cyanide to enones.

Definition

ChEBI: An alicyclic ketone that is cyclopentanone substituted at position 3 by a cyano group.

Synthesis Reference(s)

The Journal of Organic Chemistry, 38, p. 3455, 1973 DOI: 10.1021/jo00960a002

Synthesis

General procedure for the synthesis of 3-oxocyclopentanecarbonitrile from 2-cyclopentenone: a mixed solution of 2-cyclopentenone (10 g, 122 mmol), potassium cyanide (9.5 g, 146 mmol), and triethylamine hydrochloride (25 g, 83 mmol) in methanol (150 mL) was stirred for 4 hours at room temperature. Upon completion of the reaction, the reaction mixture was concentrated; the residue was redissolved in ethyl acetate. The resulting solution was washed sequentially with water and saturated saline, dried over anhydrous sodium sulfate and concentrated. The residue was purified by silica gel column chromatography (petroleum ether: ethyl acetate = 5:1) to give 7.5 g of 3-oxocyclopentanecarbonitrile.1H NMR (400 MHz, CDCl3): δ 3.13-3.51 (m, 1H), 2.56-2.63 (m, 1H), 2.16-2.48 (m, 5H).

References

[1] Journal of Organic Chemistry, 1997, vol. 62, # 15, p. 5144 - 5155
[2] Chemical and Pharmaceutical Bulletin, 1985, vol. 33, # 5, p. 2164 - 2167
[3] Patent: WO2013/28670, 2013, A1. Location in patent: Page/Page column 119; 120

3-Oxo-cyclopentanecarbonitrile(41171-91-9)Related Product Information

• 3-OXO-1-CYCLOHEXANECARBOXYLIC ACID 96