Ethyl 2-cyano-3,3-diphenylacrylate Property

Melting point:

97-99 °C(lit.)

Boiling point:

174 °C0.2 mm Hg(lit.)

Density 

1,05 g/cm³

refractive index 

1.5100 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

color 

White to Almost white

InChI

InChI=1S/C18H15NO2/c1-2-21-18(20)16(13-19)17(14-9-5-3-6-10-14)15-11-7-4-8-12-15/h3-12H,2H2,1H3

InChIKey

IAJNXBNRYMEYAZ-UHFFFAOYSA-N

SMILES

C(OCC)(=O)/C(/C#N)=C(/C1=CC=CC=C1)\C1=CC=CC=C1

LogP

4.520 (est)

CAS DataBase Reference

5232-99-5(CAS DataBase Reference)

EPA Substance Registry System

Ethyl 2-cyano-3,3-diphenylacrylate (5232-99-5)

Safety

Hazard Codes 

Xi,N

Risk Statements 

36/37/38-50/53

Safety Statements 

26-36-60-61

RIDADR 

UN 3077 9/PG 3

WGK Germany 

3

RTECS 

AT6200000

HS Code 

29269090

Hazardous Substances Data

5232-99-5(Hazardous Substances Data)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

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

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P273Avoid release to the environment.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Ethyl 2-cyano-3,3-diphenylacrylate Chemical Properties,Usage,Production

Description

Etocrylene (Ethyl 2-cyano-3,3-diphenylacrylate) is an organic ester that appears as an off-white crystalline powder and functions as a UV absorber. When applied to the skin, this product absorbs UV rays. It can also be used to protect cosmetics and personal care products from deterioration. This product can be used in the formulation of sun protection products, as well as bath, skin, cleansing, hair, nail and fragrance products.

Uses

Ultraviolet screen.

Uses

Ethyl 2-Cyano-3,3-diphenylacrylate is a sunscreen ingredient.

Synthesis Reference(s)

Journal of the American Chemical Society, 63, p. 3452, 1941 DOI: 10.1021/ja01857a057
Tetrahedron Letters, 33, p. 7535, 1992 DOI: 10.1016/S0040-4039(00)60817-1

Synthesis

The preparation method of Ethyl 2-cyano-3,3-diphenylacrylate includes the following steps: add cyclohexane and benzophenone to the reaction kettle, wait until the benzophenone is completely dissolved, then raise the temperature to 102-104°C and keep it warm. Then, add sodium bicarbonate as a catalyst, add ethyl cyanoacetate into the dripping storage tank, slowly add ethyl cyanoacetate dropwise into the reaction kettle, and react for 16 to 18 hours. During the reaction, the water generated is separated in time, and the reaction is completed. The product Ethyl 2-cyano-3,3-diphenylacrylate is obtained.

Properties and Applications

Ethyl 2-cyano-3,3-diphenylacrylate, another name Etocrylene, belongs to acrylic acid or the like UV light absorbers and is mainly used in making UV light absorbers in plastics, coating, dyestuff, vehicle glass, makeup, sun-screening agent. Because acrylate-based, two phenyls of this product and carbonyl can form a larger π key; thus, the structure shape of this product has extremely strong ultraviolet absorption ability.

References

[1] Hisashi Matsumoto, Yasuhiko Suzuki, Shinichi Adachi. “[Estrogenic activity of ultraviolet absorbers and the related compounds].” Yakugaku zasshi?: Journal of the Pharmaceutical Society of Japan 125 8 (2005): 643–52.
[2] Marlene Vila . “Ultrasound-assisted emulsification microextraction followed by gas chromatography–mass spectrometry and gas chromatography–tandem mass spectrometry for the analysis of UV filters in water.” Microchemical Journal 124 (2016): Pages 530-539.