2-Cyanotetrahydrofuran

2-Cyanotetrahydrofuran Property

storage temp. 

Sealed in dry,Store in freezer, under -20°C

Appearance

Colorless to light yellow Liquid

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H301Toxic if swalloed

H311Toxic in contact with skin

H331Toxic if inhaled

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P311Call a POISON CENTER or doctor/physician.

2-Cyanotetrahydrofuran Chemical Properties,Usage,Production

Synthesis

General procedure for the synthesis of 2-cyanotetrahydrofuran from tetrahydrofuran-2-carboxamide: Preparation of 2-cyanotetrahydrofuran. Trifluoroacetic anhydride (1.55 g, 7.38 mmol) was slowly added to an anhydrous 1,4-dioxane (10 mL) ice-cold solution (0 °C) of tetrahydrofuran-2-carboxamide (0.77 g, 6.71 mmol) and pyridine (1.06 g, 13.42 mmol) at a rate of one drop every 10 seconds. The addition of trifluoroacetic anhydride was monitored to ensure that the internal temperature was below 5 °C and that the addition was completed within 20 min. The reaction mixture was gradually warmed to room temperature and stirred continuously for 3 hours. Upon completion of the reaction, chloroform (100 mL) was added to the mixture and extracted sequentially with water (30 mL) and saturated aqueous sodium chloride solution (20 mL). The organic phases were combined, dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give the crude product. The crude product was purified by fast column chromatography (eluent: hexane to 25% ethyl acetate/hexane gradient elution) to afford 2-cyanotetrahydrofuran (0.51 g, 62% yield) as a colorless oil.1H NMR (CDCl3, 300 MHz) δ: 4.70 (1H, m), 3.96 (2H, m), 2.24 (2H, m), 2.08 (2H, m). m).

References

[1] Patent: US2005/187266, 2005, A1
[2] Patent: WO2004/92145, 2004, A1. Location in patent: Page 137