Product Name

  • Name

    Octocrilene

  • EINECS 228-250-8
  • CAS No. 6197-30-4
  • Article Data28
  • CAS DataBase
  • Density 1.055 g/cm3
  • Solubility Insoluble in water
  • Melting Point -10 °C
  • Formula C24H27NO2
  • Boiling Point 478.5 °C at 760 mmHg
  • Molecular Weight 361.484
  • Flash Point 239.5 °C
  • Transport Information
  • Appearance Yellow viscous liquid
  • Safety 29/56
  • Risk Codes 52
  • Molecular Structure Molecular Structure of 6197-30-4 (Octocrilene)
  • Hazard Symbols
  • Synonyms Acrylicacid, 2-cyano-3,3-diphenyl-, 2-ethylhexyl ester (7CI,8CI);2-Cyano-3,3-diphenylacrylic acid 2-ethylhexyl ester;2-Ethylhexyl 2-cyano-3,3-diphenylacrylate;2-Ethylhexyl a-cyano-b,b'-diphenylacrylate;2-Ethylhexyl a-cyano-b-phenylcinnamate;CA 1 (light stabilizer);Escalol597;Eusolex OCR;Neo Heliopan 303;Parsol 340;Sanduvor 3039;Uvinul 3039;Uvinul N 539SG;Viosorb 930;
  • PSA 50.09000
  • LogP 5.77168

Synthetic route

2-Ethylhexyl alcohol
104-76-7

2-Ethylhexyl alcohol

etocrylene
5232-99-5

etocrylene

octocrylene
6197-30-4

octocrylene

Conditions
ConditionsYield
In sodium carbonate99.8%
With sodium methylate In toluene for 8h; Reflux;144.3 g
benzophenone
119-61-9

benzophenone

2'-ethylhexyl cyanoacetate
13361-34-7

2'-ethylhexyl cyanoacetate

octocrylene
6197-30-4

octocrylene

Conditions
ConditionsYield
With ammonium acetate; acetic acid In water at 85 - 90℃; under 400 - 420 Torr; for 16h; Reagent/catalyst;76.3%
With propionic acid; ammonium acetate In n-heptane at 110℃; under 760.051 Torr; for 5h; Product distribution / selectivity;66.18%
benzophenone
119-61-9

benzophenone

2'-ethylhexyl cyanoacetate
13361-34-7

2'-ethylhexyl cyanoacetate

A

2-cyano-3,3-diphenylacrylamide
731-48-6

2-cyano-3,3-diphenylacrylamide

B

octocrylene
6197-30-4

octocrylene

Conditions
ConditionsYield
With propionic acid; ammonium acetate In n-heptane at 95 - 110℃; under 525.053 - 760.051 Torr; for 6h; Product distribution / selectivity; Heating / reflux;A 0.42 - 0.7 %Chromat.
B n/a
...Expand
benzophenone
119-61-9

benzophenone

octocrylene
6197-30-4

octocrylene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: ammonium acetate; pyrographite / n-heptane / 15 h / Ionic liquid; Reflux
2: sodium methylate / toluene / 8 h / Reflux
View Scheme
octocrylene
6197-30-4

octocrylene

2-cyano-3,3-diphenyl-propionic acid 2-ethylhexyl ester

2-cyano-3,3-diphenyl-propionic acid 2-ethylhexyl ester

Conditions
ConditionsYield
With hydrogen; 5%-palladium/activated carbon In tetrahydrofuran at 20℃;
ethanol
64-17-5

ethanol

octocrylene
6197-30-4

octocrylene

A

etocrylene
5232-99-5

etocrylene

B

2-ethylhexyl 2-ethoxy-4-phenylquinoline-3-carboxylate

2-ethylhexyl 2-ethoxy-4-phenylquinoline-3-carboxylate

Conditions
ConditionsYield
for 6h; Photolysis;
...Expand
benzylamine
100-46-9

benzylamine

octocrylene
6197-30-4

octocrylene

N-benzyl-2-cyano-3,3-diphenylacrylamide

N-benzyl-2-cyano-3,3-diphenylacrylamide

Conditions
ConditionsYield
In cyclohexane for 3h; Photolysis;
octocrylene
6197-30-4

octocrylene

C41H51NO5

C41H51NO5

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium hydroxide; water / ethanol / 24 h / 20 °C
2.1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 2 h / 25 °C / Inert atmosphere
2.2: 5 h / 25 °C / Inert atmosphere
View Scheme
octocrylene
6197-30-4

octocrylene

2-cyano-3,3-diphenylacrylic acid
10380-41-3

2-cyano-3,3-diphenylacrylic acid

Conditions
ConditionsYield
With water; sodium hydroxide In ethanol at 20℃; for 24h;

Octocrilene Specification

The IUPAC name of Octocrilene is 2-ethylhexyl 2-cyano-3,3-diphenylprop-2-enoate. With the CAS registry number 6197-30-4, it is also named as 2-Propenoic acid, 2-cyano-3,3-diphenyl-, 2-ethylhexyl ester. The product's categories are cosmetic raw material; UV-Absorber; Stabilizers; Polymer Additives; Polymer Science. It is clear and colorless viscous liquid which is probably combustible. And it is an ester formed by the condensation of a diphenylcyanoacrylate with 2-ethylhexanol. When heated to decomposition it emits toxic vapors of NOx. Additionally, this chemical should be sealed in the container and stored in the cool and dry place.

The other characteristics of Octocrilene can be summarized as: (1)ACD/LogP: 7.53; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 7.53; (4)ACD/LogD (pH 7.4): 7.53; (5)#H bond acceptors: 3; (6)#H bond donors: 0; (7)#Freely Rotating Bonds: 10 ; (8)Index of Refraction: 1.545; (9)Molar Refractivity: 108.36 cm3; (10)Molar Volume: 342.4 cm3; (11)Polarizability: 42.96×10-24 cm3; (12)Surface Tension: 41.5 dyne/cm; (13)Enthalpy of Vaporization: 74.26 kJ/mol; (14)Boiling Point: 478.5 °C at 760 mmHg; (15)Vapour Pressure: 2.56E-09 mmHg at 25°C; (16)Rotatable Bond Count: 10; (17)Exact Mass: 361.204179; (18)MonoIsotopic Mass: 361.204179; (19)Topological Polar Surface Area: 50.1; (20)Heavy Atom Count: 27; (21)Complexity: 510.

Uses of Octocrilene: It is used as ultraviolet absorber in plastics, paints and dyes. And it is also used as an ingredient in sunscreens and cosmetics that is protecting the skin from direct DNA damage. In additin, this chemical can penetrate into the skin where it acts as a photosensitizer.

People can use the following data to convert to the molecule structure. 
1. SMILES:N#C/C(C(=O)OCC(CC)CCCC)=C(/c1ccccc1)c2ccccc2
2. InChI:InChI=1/C24H27NO2/c1-3-5-12-19(4-2)18-27-24(26)22(17-25)23(20-13-8-6-9-14-20)21-15-10-7-11-16-21/h6-11,13-16,19H,3-5,12,18H2,1-2H3

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rat LD50 oral > 5gm/kg (5000mg/kg)   National Technical Information Service. Vol. OTS0556792,

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