Cinnamonitrile

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Name: Cinnamonitrile

Alias: Cinnamonitrilecistrans; 3-Phenylacrylonitrile; (2E)-3-phenylprop-2-enenitrile; (2Z)-3-phenylprop-2-enenitrile

CAS Number: 1885-38-7; 4360-47-8

Molecular Formula: C9H7N

 

Linear Formula C6H5CH=CHCN

Molecular Weight 129.16

Purity: ≥98%

Beilstein Registry Number 1209546

EC Number 217-552-5

 

Appearance: Colorless to yellowish liquid, the aroma is very similar to natural cinnamon, with strong spicy fragrance.

Melting point: 18-20°C(lit.)

Boiling point: 254-255 °C(lit.)

Density : 1.028 g/mL at 25 °C(lit.)

Flash Point(C): 113°C

refractive index : n20/D 1.601(lit.)

 

Preparation

The aqueous solution of hydroxylamine hydrochloride and sodium carbonate was prepared by mixing anhydrous sodium carbonate, hydroxylamine hydrochloride and water. Then the aqueous solution of hydroxylamine hydrochloride and sodium carbonate was added to the solution of cinnamaldehyde and ethanol or methanol, stirred and set it well. Then the reaction mixture was poured into the ice water until the white precipitate was precipitated, the white precipitate was filtered out and washed with water, then the cinnamaldehyde oxime was obtained after drying. Acetic anhydride of 2o 2.5 times (mole ratio) was dripped into cinnamaldehyde oxime, stirred for dehydration and cooled, then vacuum distillation was used to recover acetic anhydride and acetic acid produced by the reaction, and then vacuum distillation was carried out. Cinnamonitrile was obtained by collecting stable fractions at 130C / 2064pa or 151.0 ℃ / 5330pa. The method has the advantages of simple operation, low raw material, no pollution and high yield.

 

Rapid Synthesis of Trans-cinnamonitrile

Acetonitrile, potassium hydroxide and benzaldehyde were used as raw materials in acetonitrile solvent, stirred and refluxed (10 min), hydrolyzed by crushed ice, heated under normal pressure and distilled under reduced pressure to rapidly synthesize trans-cinnamonitrile. The yield was 48%-54%. The application of organic carbon anion nucleophilic addition reaction mechanism in organic synthesis was studied. The structure of the product was characterized by UV-Vis, FTIR and HNMR, and it was confirmed that the product was the target product. The results showed that trans cinnamonitrile could be synthesized rapidly under mild conditions using potassium hydroxide benzaldehyde and acetonitrile as raw materials according to the mechanism of nucleophilic addition of organic carbon anion.

 

Usage:

The performance is stable under alkaline condition. No toxic side effects to human body, no irritation to the skin, no allergic reaction. Cinnamonitrile is an ideal substitute for cinnamon oil and cinnamaldehyde. Widely used in cosmetics, spice, laundry powder and other daily necessities and soap spices. It has good inhibition effect on mold, wide inhibition spectrum and insect repellent effect. At the same time, it is also used in medicine, fine chemical products. It's a good synthetic product.

 




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