Octyl 4-methoxycinnamate supplier

Name
Octyl 4-methoxycinnamate
EINECS 226-775-7
CAS No. 5466-77-3
Article Data61
CAS DataBase
Density 1 g/cm³
Solubility <0.1 g/100 mL at 27 °C in water
Melting Point <-25℃
Formula C₁₈H₂₆O₃
Boiling Point 405.3 °C at 760 mmHg
Molecular Weight 290.403
Flash Point 171.6 °C
Transport Information
Appearance colourless or pale yellow liquid
Safety 24/25
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 2-Ethylhexyl4-methoxycinnamate;2-Ethylhexyl p-methoxycinnamate;4-Methoxycinnamic acid2-ethylhexyl ester;Ethylhexyl p-methoxycinnamate;Eusolex UV-Pearls OMC;Octinoxate;Octylmethoxycinnamate;Octyl p-methoxycinnamate;Parsol MCX;Tinosorb OMC;Uvinul 3088;p-Methoxycinnamic acid 2-ethylhexyl ester;
PSA 35.53000
LogP 4.46800

Synthetic route

: diazo-acetic acid-(2-ethyl-hexyl ester)

: 123-11-5
4-methoxy-benzaldehyde

: 5466-77-3
2-ethylhexyl methoxycinnamate

Conditions

Conditions	Yield
With Fe(TCP)Cl; polyethylene supported arsine; polymethylhydrosiloxane In toluene at 110℃; for 20h; Wittig type reaction; Inert atmosphere; stereoselective reaction;	98%

: 103-11-7
2-Ethylhexyl acrylate

: 696-62-8
para-iodoanisole

: 5466-77-3
2-ethylhexyl methoxycinnamate

Conditions

Conditions	Yield
With tetrabutylammomium bromide; C32H26Cl2N8O4Pd2; potassium carbonate In methanol; water for 0.416667h; Reflux;	97%
With C43H54NO5P; palladium diacetate; triethylamine In water at 40℃; for 12h; Heck Reaction;	95%
With tributyl-amine; chloro-[2-(9-phenyl-1,10-phenanthrolin-2-yl)phenyl]palladium In 1-methyl-pyrrolidin-2-one at 140℃; for 15h; Heck Reaction; Inert atmosphere;	94%

: 103-11-7
2-Ethylhexyl acrylate

: 459-64-3
4-methoxybenzenediazonium tetrafluoroborate

: 5466-77-3
2-ethylhexyl methoxycinnamate

Conditions

Conditions	Yield
[(1,3-dimesitylimidazol-2-ylidene)(benzoquinone)Pd(0)]2 In methanol at 50℃; for 1h; Heck reaction;	96%
With calcium carbonate; Lindlar's catalyst In methanol	93%
(IMes)Pd(NQ) In ethanol at 50℃; for 1h; Conversion of starting material; Heck Reaction;	88%
palladium on activated carbon In dichloromethane; water; dimethyl sulfoxide	80%
With xonotlite; palladium diacetate In methanol at 20℃; Reagent/catalyst;	73%

: 104-76-7
2-Ethylhexyl alcohol

: 24393-56-4
ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate

: 5466-77-3
2-ethylhexyl methoxycinnamate

Conditions

Conditions	Yield
With toluene-4-sulfonic acid Heating;	94%

: 107-45-9
tert-Octylamine

: 103-11-7
2-Ethylhexyl acrylate

: 696-62-8
para-iodoanisole

: 5466-77-3
2-ethylhexyl methoxycinnamate

Conditions

Conditions	Yield
With acetic acid; palladium on charcoal	92%

...Expand

palladium of charcoal: palladium of charcoal

: 103-11-7
2-Ethylhexyl acrylate

: 696-62-8
para-iodoanisole

: 5466-77-3
2-ethylhexyl methoxycinnamate

Conditions

Conditions	Yield
With triethylamine In water; toluene	92%

...Expand

: 104-76-7
2-Ethylhexyl alcohol

: 79-20-9
acetic acid methyl ester

: 123-11-5
4-methoxy-benzaldehyde

A: 103-09-3
2-ethylhexyl acetate

B: 5466-77-3
2-ethylhexyl methoxycinnamate

Conditions

Conditions	Yield
Stage #1: 2-Ethylhexyl alcohol; acetic acid methyl ester; 4-methoxy-benzaldehyde With sodium methylate at 20 - 100℃; under 45.0045 Torr; for 3.33333h; Stage #2: With sulfuric acid; toluene-4-sulfonic acid In water at 100℃; for 0.25h;	A n/a B 91.5%
Stage #1: 2-Ethylhexyl alcohol; acetic acid methyl ester; 4-methoxy-benzaldehyde With sodium methylate at 20 - 100℃; under 45.0045 Torr; for 3.33333h; Stage #2: With sulfuric acid In water at 100 - 150℃; for 2.25h;	A n/a B 90%

...Expand

: 103-11-7
2-Ethylhexyl acrylate

: 4180-23-8
E-1-(4'-methoxyphenyl)prop-1-ene

: 5466-77-3
2-ethylhexyl methoxycinnamate

Conditions

Conditions	Yield
With Hoveyda-Grubbs catalyst first generation In 1,2-dichloro-ethane at 70℃; Cross Metathesis; Schlenk technique; Inert atmosphere; Glovebox;	89%
With Hoveyda-Grubbs catalyst second generation In toluene at 70℃; for 6h; Inert atmosphere; Glovebox;	> 99 %Spectr.
With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In 1,2-dichloro-ethane at 70℃; for 4h; Solvent; Reagent/catalyst; Inert atmosphere; Glovebox;
With 1,3-bis-(2,4,6-trimethylphenyl)-2-(imidazolidinylidene)dichloro(5-nitro-2-isopropoxyphenylmethylene)ruthenium; 2,6-di-tert-butyl-4-methyl-phenol In toluene at 70℃; for 1.5h; Catalytic behavior; Inert atmosphere; Schlenk technique;	86 %Chromat.

: 94-96-2
2-ethyl-1,3-hexane diol

: 103-11-7
2-Ethylhexyl acrylate

: 107-21-1
ethylene glycol

: 5466-77-3
2-ethylhexyl methoxycinnamate

Conditions

Conditions	Yield
With sodium carbonate; triphenylphosphine; palladium diacetate In 1-bromo-4-methoxy-benzene	88%

...Expand

: 103-11-7
2-Ethylhexyl acrylate

: 696-62-8
para-iodoanisole

: 109-89-7
diethylamine

: 5466-77-3
2-ethylhexyl methoxycinnamate

Conditions

Conditions	Yield
With acetic acid; palladium on charcoal	86.6%

...Expand

: 103-11-7
2-Ethylhexyl acrylate

: 1-(benzoyl)piperidine-2,6-dione

: 5466-77-3
2-ethylhexyl methoxycinnamate

Conditions

Conditions	Yield
With lithium bromide; palladium dichloride In 1-methyl-pyrrolidin-2-one at 160℃; for 15h; Heck Reaction; Inert atmosphere; chemoselective reaction;	84.8%

: 15795-54-7
5-(4-methoxybenzylidene)-2,2-dimethyl-[1,3]dioxane-4,6-dione

: 104-76-7
2-Ethylhexyl alcohol

: 5466-77-3
2-ethylhexyl methoxycinnamate

Conditions

Conditions	Yield
Stage #1: 5-(4-methoxybenzylidene)-2,2-dimethyl-[1,3]dioxane-4,6-dione; 2-Ethylhexyl alcohol With iron(III) chloride hexahydrate In nitromethane for 0.25h; Microwave irradiation; Stage #2: With piperidine In nitromethane for 0.25h; Microwave irradiation; stereoselective reaction;	84%

: 104-92-7
1-bromo-4-methoxy-benzene

: 103-11-7
2-Ethylhexyl acrylate

: 5466-77-3
2-ethylhexyl methoxycinnamate

Conditions

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium (0); tri-tert-butyl phosphine; Cy2NMe2 In 1,4-dioxane at 20℃; for 148h; Heck coupling;	83%
With C21H21ClN4Pd; triethylamine In 1-methyl-pyrrolidin-2-one at 140℃; for 8h;	73%
With sodium acetate; *6Ph4PCl In various solvent(s) at 130℃;	71%
With tri-n-propylamine In 1-methyl-pyrrolidin-2-one at 175℃; for 24h; Heck reaction; Inert atmosphere;	34%
With dimethylaminoacetic acid; bis(benzonitrile)palladium(II) dichloride

: 103-11-7
2-Ethylhexyl acrylate

: 623-12-1
4-chloromethoxybenzene

: 5466-77-3
2-ethylhexyl methoxycinnamate

Conditions

Conditions	Yield
With potassium phosphate; catacxium A; bis(dibenzylideneacetone)-palladium(0) In 1,4-dioxane at 120℃; for 24h; Substitution; Heck reaction;	82%

methanolic sodium methylate: methanolic sodium methylate

: 353-42-4
boron trifluoride dimethyl etherate

: 104-76-7
2-Ethylhexyl alcohol

: 2186-92-7
p-Anisaldehyde dimethyl acetal

: 69098-08-4
methyl 3-(4-methoxyphenyl)-3-methoxypropanoate

: 5466-77-3
2-ethylhexyl methoxycinnamate

Conditions

Conditions	Yield
	75%

...Expand

: 103-11-7
2-Ethylhexyl acrylate

: 4180-23-8
E-1-(4'-methoxyphenyl)prop-1-ene

A: 4705-34-4, 15638-14-9, 34480-01-8, 112246-67-0, 2510-75-0
1,2-bis(4-methoxyphenyl)ethene

B: 5466-77-3
2-ethylhexyl methoxycinnamate

Conditions

Conditions	Yield
With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; p-cresol In dichloromethane for 2h; Reflux; Inert atmosphere;	A 53% B 47%
With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In 1,2-dichloro-ethane at 70℃; for 4h; Reagent/catalyst; Inert atmosphere; Glovebox;

...Expand

: 103-11-7
2-Ethylhexyl acrylate

: 5466-77-3
2-ethylhexyl methoxycinnamate

Conditions

Conditions	Yield
	40%

: 123-11-5
4-methoxy-benzaldehyde

α-hydrazino-phenylacetic acid: α-hydrazino-phenylacetic acid

: 5466-77-3
2-ethylhexyl methoxycinnamate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 99 percent / 4-(dimethylamino)pyridine / dimethylformamide / 25 °C 2: 94 percent / p-TsOH / Heating View Scheme
Multi-step reaction with 2 steps 1: 97 percent / 4-(dimethylamino)pyridine; acetic acid; piperidine / dimethylformamide / 10 - 25 °C 2: 94 percent / p-TsOH / Heating View Scheme

conc. H2 SO4: conc. H2 SO4

: 463-04-7
n-Amyl nitrite

: 103-11-7
2-Ethylhexyl acrylate

: 104-94-9
4-methoxy-aniline

: 5466-77-3
2-ethylhexyl methoxycinnamate

Conditions

Conditions	Yield
palladium diacetate In 2-Ethylhexyl alcohol

...Expand

: 104-76-7
2-Ethylhexyl alcohol

: 103-11-7
2-Ethylhexyl acrylate

A sodium bromide: sodium bromide

B: 5466-77-3
2-ethylhexyl methoxycinnamate

Conditions

Conditions	Yield
With sodium carbonate; triphenylphosphine; palladium diacetate In 1-bromo-4-methoxy-benzene

...Expand

: 104-92-7
1-bromo-4-methoxy-benzene

: 103-11-7
2-Ethylhexyl acrylate

: 5137-55-3
Aliquat 336

: 5466-77-3
2-ethylhexyl methoxycinnamate

Conditions

Conditions	Yield
With sodium carbonate; triphenylphosphine; palladium diacetate

...Expand

MTB ether: MTB ether

: 103-11-7
2-Ethylhexyl acrylate

: 623-12-1
4-chloromethoxybenzene

: 2622-14-2
tricyclohexylphosphine

: 5466-77-3
2-ethylhexyl methoxycinnamate

Conditions

Conditions	Yield
With sodium carbonate; palladium diacetate

...Expand

: 140-67-0
Estragole

: 5466-77-3
2-ethylhexyl methoxycinnamate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: carbonylchlorohydridotris(triphenylphosphine)ruthenium(II) / toluene / 0.25 h / 40 °C / Inert atmosphere; Glovebox 2: Hoveyda-Grubbs catalyst second generation / toluene / 6 h / 70 °C / Inert atmosphere; Glovebox View Scheme
Multi-step reaction with 2 steps 1: [CpRu(PN)(MeCN)]PF6 / toluene / 0.5 h / 40 °C / Inert atmosphere; Glovebox 2: Hoveyda-Grubbs catalyst second generation / toluene / 6 h / 70 °C / Inert atmosphere; Glovebox View Scheme

: 103-11-7
2-Ethylhexyl acrylate

: 4180-23-8
E-1-(4'-methoxyphenyl)prop-1-ene

A: 637-69-4
4-Methoxystyrene

B: 5466-77-3
2-ethylhexyl methoxycinnamate

Conditions

Conditions	Yield
With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In 1,2-dichloro-ethane at 70℃; for 1h; Inert atmosphere; Glovebox;

...Expand

: 103-11-7
2-Ethylhexyl acrylate

: 4180-23-8
E-1-(4'-methoxyphenyl)prop-1-ene

A: 637-69-4
4-Methoxystyrene

B: 4705-34-4, 15638-14-9, 34480-01-8, 112246-67-0, 2510-75-0
1,2-bis(4-methoxyphenyl)ethene

C: 5466-77-3
2-ethylhexyl methoxycinnamate

Conditions

Conditions	Yield
With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In toluene at 70℃; for 4h; Reagent/catalyst; Inert atmosphere; Glovebox;

...Expand

: 5466-77-3
2-ethylhexyl methoxycinnamate

: 127794-13-2
3-(4-methoxy-phenyl)-propionic acid 2-ethyl-hexyl ester

Conditions

Conditions	Yield
With Triethoxysilane; water; palladium diacetate In tetrahydrofuran Ambient temperature;	92%

: 7145-99-5
5-methyl-1,3-benzodioxole

: 5466-77-3
2-ethylhexyl methoxycinnamate

: 2'-ethylhexyl 3-(2-methyl-4,5-methylenedioxyphenyl)-3-(4-methoxyphenyl)propionate

Conditions

Conditions	Yield
With palladium diacetate; trifluoroacetic acid In dichloromethane at 20℃; for 10h; Hydroarylation;	86%
With trifluoroacetic acid; palladium diacetate In dichloromethane at 20℃; for 10h; hydroarylation;	85%

: 5466-77-3
2-ethylhexyl methoxycinnamate

: 150-78-7
1,4-dimethoxybezene

: 2'-ethylhexyl 3-(2,5-dimethoxyphenyl)-3-(4-methoxyphenyl)propionate

Conditions

Conditions	Yield
With palladium diacetate; trifluoroacetic acid In dichloromethane at 20℃; for 10h; Hydroarylation;	83%

: 621-23-8
1,2,3-trimethoxybenzene

: 5466-77-3
2-ethylhexyl methoxycinnamate

: 2'-ethylhexyl 3-(2,4,6-trimethoxyphenyl)-3-(4-methoxyphenyl)propionate

Conditions

Conditions	Yield
With palladium diacetate; trifluoroacetic acid In dichloromethane at 20℃; for 10h; Hydroarylation;	65%

: 5466-77-3
2-ethylhexyl methoxycinnamate

A: 1619923-81-7
2-hydroxymethyl-3-(p-methoxyphenyl)-1-phenylamino-1,2,3,4-tetrahydronaphthalene

B: 2-hydroxymethyl-3-(p-methoxyphenyl)-1-phenylamino-1,2,3,4-tetrahydronaphthalene

C: 2-hydroxymethyl-3-(p-methoxyphenyl)-1-phenylamino-1,2,3,4-tetrahydronaphthalene

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: diisobutylaluminium hydride / hexane / 2 h / 0 °C 2.1: dipyridinium dichromate; aluminum oxide / dichloromethane / 24 h / 20 °C 3.1: L-proline; acetic acid / methanol; acetonitrile / 5 h / 20 °C 3.2: 1 h / 20 °C View Scheme

...Expand

: 5466-77-3
2-ethylhexyl methoxycinnamate

A: 1619923-81-7
2-hydroxymethyl-3-(p-methoxyphenyl)-1-phenylamino-1,2,3,4-tetrahydronaphthalene

B: 2-hydroxymethyl-3-(p-methoxyphenyl)-1-phenylamino-1,2,3,4-tetrahydronaphthalene

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: diisobutylaluminium hydride / hexane / 2 h / 0 °C 2.1: dipyridinium dichromate; aluminum oxide / dichloromethane / 24 h / 20 °C 3.1: L-proline; acetic acid / methanol; acetonitrile / 5 h / 20 °C 3.2: 1 h / 20 °C View Scheme

: 5466-77-3
2-ethylhexyl methoxycinnamate

A: 1619923-76-0
C24H23NO2

B: C24H23NO2

C: C24H23NO2

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: diisobutylaluminium hydride / hexane / 2 h / 0 °C 2: dipyridinium dichromate; aluminum oxide / dichloromethane / 24 h / 20 °C 3: L-proline; acetic acid / methanol; acetonitrile / 5 h / 20 °C View Scheme

...Expand

Octyl 4-methoxycinnamate Specification

The IUPAC name of Octyl 4-methoxycinnamate is 2-ethylhexyl (E)-3-(4-methoxyphenyl)prop-2-enoate. With the CAS registry number 5466-77-3, it is also named as 2-Ethylhexyl methoxycinnamate. The product's categories are Cosmetic Raw Material; UV-Absorber. It is colourless or pale yellow liquid which is probably combustible, stable and incompatible with strong oxidizing agents. Additionally, this chemical should be sealed in the container and stored in the cool and dry place.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 5.66; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 5.66; (4)ACD/LogD (pH 7.4): 5.66; (5)ACD/BCF (pH 5.5): 11740.24; (6)ACD/BCF (pH 7.4): 11740.24; (7)ACD/KOC (pH 5.5): 28488.09; (8)ACD/KOC (pH 7.4): 28488.09; (9)#H bond acceptors: 3; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 10; (12)Index of Refraction: 1.515; (13)Molar Refractivity: 87.61 cm³; (14)Molar Volume: 290.3 cm³; (15)Polarizability: 34.73×10^-24 cm³; (16)Surface Tension: 35.2 dyne/cm; (17)Enthalpy of Vaporization: 65.68 kJ/mol; (18)Vapour Pressure: 8.89E-07 mmHg at 25°C; (19)Rotatable Bond Count: 10; (20)Exact Mass: 290.188195; (21)MonoIsotopic Mass: 290.188195; (22)Topological Polar Surface Area: 35.5; (23)Heavy Atom Count: 21; (24)Complexity: 304.

Preparation of Octyl 4-methoxycinnamate: Adding p-toluenesulfonic acid to the mixture of octanol, anisaldehyde, malonic acid and pyridine. After esterification, we carry on neutralization, dehydration, azeotropic distillation and refining to get the product.

Uses of Octyl 4-methoxycinnamate: It is mainly used to absorb UV-B and UV-A rays from the sun, protecting the skin from damage, so it is used is in suncreens and other cosmetics. And it is also used to reduce the appearance of scars. In addition, it can react with hexadecan-1-ol to get n-hexadecyl 4-methoxycinnamate and 2-ethyl-hexan-1-ol. This reaction needs reagent AlCl₃*6H₂O. The yield is 75%.

People can use the following data to convert to the molecule structure.
1. SMILES:O=C(OCC(CC)CCCC)\C=C\c1ccc(OC)cc1
2. InChI:InChI=1/C18H26O3/c1-4-6-7-15(5-2)14-21-18(19)13-10-16-8-11-17(20-3)12-9-16/h8-13,15H,4-7,14H2,1-3H3/b13-10+

Product Name

Octyl 4-methoxycinnamate

Synthetic route

Octyl 4-methoxycinnamate Specification

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