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Ethyl 2-cyano-3,3-diphenylacrylate

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Ethyl 2-cyano-3,3-diphenylacrylate Basic information

Product Name:
Ethyl 2-cyano-3,3-diphenylacrylate
Synonyms:
  • 2-cyano-3,3-diphenyl-2-propenoicaciethylester
  • 2-cyano-3,3-diphenyl-acrylicaciethylester
  • 2-Propenoicacid,2-cyano-3,3-diphenyl-,ethylester
  • uvabsorber-2
  • uvinuln35
  • ETHYL DIPHENYLMETHYLENECYANOACETATE
  • ETHYL 2-CYANO-3,3-DIPHENYLACRYLATE
  • ETHYL-2-CYANO-3,3-DIPHENYLPROPENOATE
CAS:
5232-99-5
MF:
C18H15NO2
MW:
277.32
EINECS:
226-029-0
Product Categories:
  • C12 to C63Polymer Science
  • Carbonyl Compounds
  • Esters
  • Polymer Additives
  • Stabilizers
  • 1
Mol File:
5232-99-5.mol
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Ethyl 2-cyano-3,3-diphenylacrylate Chemical Properties

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)
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Safety Information

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)

MSDS

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Ethyl 2-cyano-3,3-diphenylacrylate Usage And Synthesis

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.

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