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CAS No.: | 24393-56-4 |
---|---|
Name: | Ethyl 4-methoxycinnamate |
Article Data: | 403 |
Molecular Structure: | |
Formula: | C12H14O3 |
Molecular Weight: | 206.241 |
Synonyms: | 2-Propenoicacid, 3-(4-methoxyphenyl)-, ethyl ester, (E)-;(2E)-3-(4-Methoxyphenyl)-2-propenoic acid ethyl ester;(E)-Ethyl3-(4-methoxyphenyl)acrylate;(E)-Ethyl 4-methoxycinnamate;Ethyl(E)-3-(4-methoxyphenyl)-2-propenoate;Ethyl(E)-3-(p-methoxyphenyl)-2-propenoate;Ethyl (E)-4-methoxycinnamate;Ethyl(E)-p-methoxycinnamate;Ethyl trans-4-methoxycinnamate;Ethyltrans-p-methoxycinnamate;Solaboost SPF;trans-p-Methoxycinnamic acid ethylester; |
Density: | 1.08 g/cm3 |
Melting Point: | 49oC |
Boiling Point: | 325.1 °C at 760 mmHg |
Flash Point: | 133.8 °C |
Hazard Symbols: | 36/37/38:; |
Risk Codes: | 36/37/38 |
Safety: | 26-36/37/39 |
PSA: | 35.53000 |
LogP: | 2.27150 |
4-methoxy-benzaldehyde
ethyl (triphenylphosphoranylidene)acetate
ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate
Conditions | Yield |
---|---|
In dichloromethane at 22℃; for 16h; Wittig reaction; | 100% |
In dichloromethane at 20 - 25℃; Inert atmosphere; | 96% |
In dichloromethane at 20℃; for 16h; Inert atmosphere; | 77% |
ethyl potassium malonate
4-methoxy-benzaldehyde
ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate
Conditions | Yield |
---|---|
With acetic acid; piperidine; dmap In N,N-dimethyl-formamide at 10 - 20℃; for 24h; Product distribution / selectivity; | 100% |
With piperidine; dmap; acetic acid In N,N-dimethyl-formamide at 20℃; for 72h; | 98% |
With piperidine; dmap; acetic acid In N,N-dimethyl-formamide at 10 - 25℃; Knoevenagel reaction; | 97% |
With hydrogenchloride; piperidine; dmap In diethyl ether; N,N-dimethyl-formamide at 10 - 20℃; for 24h; Product distribution / selectivity; | 96% |
1-ethoxy-1-(trimethylsiloxy)-2-(trimethylsilyl)ethene
4-methoxy-benzaldehyde
ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate
Conditions | Yield |
---|---|
With tetrabutylammonium acetate In dichloromethane at 0℃; for 1h; | 100% |
With 1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene In acetonitrile at 0 - 20℃; Peterson Olefination; stereoselective reaction; | 82% |
ethanol
(E)-3-(4-methoxyphenyl)acrylic acid
ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate
Conditions | Yield |
---|---|
With sulfuric acid for 16h; Heating; | 99% |
With sulfuric acid for 12h; Reflux; Inert atmosphere; | 99% |
With sulfuric acid at 90℃; for 16h; | 96% |
diethoxyphosphoryl-acetic acid ethyl ester
4-methoxy-benzaldehyde
ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate
Conditions | Yield |
---|---|
With potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene at 25℃; for 24h; Horner-Wadsworth-Emmons reaction; Inert atmosphere; neat (no solvent); optical yield given as %de; stereoselective reaction; | 99% |
With tetrabutyl ammonium fluoride In tetrahydrofuran at 30℃; for 4h; Glovebox; | 99% |
With 1,8-diazabicyclo[5.4.0]undec-7-ene at 20℃; for 2h; Horner-Wadsworth-Emmons olefination; Inert atmosphere; Neat (no solvent); stereoselective reaction; | 95% |
Conditions | Yield |
---|---|
With potassium phosphate; palladium diacetate at 130℃; for 16h; Heck olefination; | 99% |
With potassium carbonate; Pd on 3-[(2-aminoethyl)amino]propyl-functionalized silica In N,N-dimethyl acetamide at 130℃; for 12h; Heck reaction; | 99% |
With tris(bipyridine)ruthenium(II) dichloride hexahydrate; palladium diacetate; triethylamine In N,N-dimethyl-formamide at 20℃; for 24h; Heck Reaction; Schlenk technique; Inert atmosphere; Cooling with liquid nitrogen; Irradiation; | 99% |
hydrogen ethyl malonate
4-methoxy-benzaldehyde
ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate
Conditions | Yield |
---|---|
With dmap In N,N-dimethyl-formamide at 25℃; Doebner-Knoevenagel reaction; | 99% |
With dmap In N,N-dimethyl-formamide at 25℃; Knoevenagel reaction; | 99% |
piperidine; dmap In N,N-dimethyl-formamide at 10 - 20℃; for 24h; Product distribution / selectivity; | 99% |
With poly{styrene-co-[4-(N-methyl-N-vinylbenzyl-amino)pyridine]-co-[1-phenyl-3-(4-vinylbenzyl)piperazine]} In N,N-dimethyl-formamide at 50℃; decarboxylative Doebner-Knoevenagel condensation reaction; optical yield given as %de; | 97% |
4-methoxy-benzaldehyde
ethyl bromoacetate
A
ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate
B
(Z)-ethyl 3-(4-methoxyphenyl)acrylate
Conditions | Yield |
---|---|
With potassium carbonate In ethanol Wittig Olefination; Milling; diastereoselective reaction; | A 98% B n/a |
With tributylphosphine; tetrakis(triphenylphosphine) palladium(0) at 110℃; for 24h; Yield given. Yields of byproduct given; | |
With sodium hydrogencarbonate; triphenylphosphine at 20℃; for 2h; Wittig reaction; Title compound not separated from byproducts.; |
(carbethoxymethyl)triphenylphosphonium bromide
4-methoxy-benzaldehyde
ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate
Conditions | Yield |
---|---|
With potassium carbonate In dichloromethane; water at 25℃; Wittig reaction; Sonication; stereoselective reaction; | 98% |
With triethylamine In dichloromethane at 20℃; for 16h; Inert atmosphere; Schlenk technique; |
4-methoxy-benzaldehyde
ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate
Conditions | Yield |
---|---|
With potassium carbonate In dichloromethane at 40℃; for 50h; Wittig reaction; Inert atmosphere; optical yield given as %de; diastereoselective reaction; | 98% |
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Molecular Structure of Ethyl 4-methoxycinnamate (CAS NO.24393-56-4):
Empirical Formula: C12H14O3
Molecular Weight: 206.2378
H bond acceptors: 3
H bond donors: 0
Freely Rotating Bonds: 5
Polar Surface Area: 35.53 Å2
Index of Refraction: 1.539
Molar Refractivity: 59.86 cm3
Molar Volume: 190.9 cm3
Surface Tension: 37.1 dyne/cm
Density: 1.08 g/cm3
Flash Point: 133.8 °C
Enthalpy of Vaporization: 56.72 kJ/mol
Boiling Point: 325.1 °C at 760 mmHg
Vapour Pressure: 0.000235 mmHg at 25°C
Melting point: 49°C
Product Categories: Cinnamic acid
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36/37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
Ethyl 4-methoxycinnamate , with CAS number of 24393-56-4, can be called 2-Propenoic acid, 3-(4-methoxyphenyl)-, ethyl ester ; 2-propenoic acid, 3-(4-methoxyphenyl)-, ethyl ester, (2E)- ; Ethyl (2E)-3-(4-methoxyphenyl)-2-propenoate ; Ethyl (2E)-3-(4-methoxyphenyl)acrylate ; ethyl (2E)-3-(4-methoxyphenyl)prop-2-enoate ; Ethyl 3-(4-methoxyphenyl)-2-propenoate ; p-Methoxycinnamic acid ethyl ester .