Product Name

  • Name

    Ethyl cinnamate

  • EINECS 203-104-6
  • CAS No. 103-36-6
  • Article Data384
  • CAS DataBase
  • Density 1.055 g/cm3
  • Solubility insoluble in water
  • Melting Point 6-8 °C(lit.)
  • Formula C11H12O2
  • Boiling Point 269.3 °C at 760 mmHg
  • Molecular Weight 176.215
  • Flash Point 148.6 °C
  • Transport Information
  • Appearance colorless liquid
  • Safety 23-24/25
  • Risk Codes 20-22
  • Molecular Structure Molecular Structure of 103-36-6 (Ethyl cinnamate)
  • Hazard Symbols
  • Synonyms Cinnamicacid, ethyl ester (6CI,7CI,8CI);3-Phenyl-2-propenoic acid ethyl ester;Ethyl3-phenyl-2-propenoate;Ethyl 3-phenylacrylate;Ethyl benzylideneacetate;Ethylcinnamate;(2E)-3-Phénylacrylate d'éthyle;(Z)-Ethyl cinnamate;2-propenoic acid, 3-phenyl-, ethyl ester, (2E)-;2-Propenoic acid, 3-phenyl-, ethyl ester, (E)-;Ethyl (2E)-3-phenyl-2-propenoate;Ethyl (2E)-3-phenylacrylate;ethyl (2E)-3-phenylprop-2-enoate;
  • PSA 26.30000
  • LogP 2.26290

Synthetic route

iodobenzene
591-50-4

iodobenzene

ethyl acrylate
140-88-5

ethyl acrylate

ethyl 3-phenyl-2-propenoate
103-36-6

ethyl 3-phenyl-2-propenoate

Conditions
ConditionsYield
Stage #1: iodobenzene; ethyl acrylate; [poly(methylphenylsilane)/inorganic compound]-supported palladium
Stage #2: With potassium carbonate In 1-methyl-pyrrolidin-2-one at 80℃; Heck Reaction;
100%
With PEG-based bis-pyridine-derived ligand; triethylamine; palladium diacetate In N,N-dimethyl-formamide at 120℃; for 8h; Heck reaction;99%
With tributyl-amine In dodecane at 130℃; for 3.5h; Heck reaction;99%
phenylpropynoic acid ethyl ester
2216-94-6

phenylpropynoic acid ethyl ester

ethyl 3-phenyl-2-propenoate
103-36-6

ethyl 3-phenyl-2-propenoate

Conditions
ConditionsYield
With formic acid; nickel dibromide; zinc In 1,4-dioxane at 120℃; for 16h; Sealed tube; stereoselective reaction;100%
With triethylsilane; indium(III) chloride; triethyl borane In hexane; acetonitrile at 0℃; for 2h;68%
With pyridine; hydrogen In methanol at 20℃; under 760.051 Torr; for 2h;
With hydrogen In [(2)H6]acetone at 25℃; under 900.09 Torr; for 0.2h; Irradiation;
bromobenzene
108-86-1

bromobenzene

ethyl acrylate
140-88-5

ethyl acrylate

ethyl 3-phenyl-2-propenoate
103-36-6

ethyl 3-phenyl-2-propenoate

Conditions
ConditionsYield
With potassium phosphate; [((ferrocenyl)(C(CH3)N(C6H4)CH3))PdCl(N,N'-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)]; tetrabutylammomium bromide In N,N-dimethyl-formamide at 140℃; for 4h; Heck reaction; Inert atmosphere;99%
With C17H19N5(2+)*2CF3O3S(1-); sodium acetate; palladium diacetate In N,N-dimethyl-formamide at 130℃; for 3.5h; Heck Reaction; Schlenk technique; Inert atmosphere;96%
With triethylamine In toluene at 80℃; for 10h; Heck Reaction;95%
2,3-dibromo-3-phenyl-propionic acid ethyl ester
5464-70-0

2,3-dibromo-3-phenyl-propionic acid ethyl ester

ethyl 3-phenyl-2-propenoate
103-36-6

ethyl 3-phenyl-2-propenoate

Conditions
ConditionsYield
With ammonium chloride; zinc In ethanol at 80℃; for 0.00833333h; microwave irradiation;98%
With potassium thioacyanate In tert-butyl alcohol for 15h; Heating;77%
With N,N,N,N,-tetramethylethylenediamine; sexithiophene In N,N-dimethyl-formamide for 1h; Inert atmosphere; Irradiation;68%
ethanol
64-17-5

ethanol

Cinnamic acid
621-82-9

Cinnamic acid

ethyl 3-phenyl-2-propenoate
103-36-6

ethyl 3-phenyl-2-propenoate

Conditions
ConditionsYield
With 4-methyl-morpholine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride for 2h;98%
With samarium(III) chloride at 80℃; for 96h; sealed tube; Inert atmosphere;96%
With methanesulfonic acid at 30 - 35℃; for 15h;95%
ethyl acrylate
140-88-5

ethyl acrylate

benzene
71-43-2

benzene

ethyl 3-phenyl-2-propenoate
103-36-6

ethyl 3-phenyl-2-propenoate

Conditions
ConditionsYield
With tert.-butylhydroperoxide In acetic acid at 100℃; for 18h; Reagent/catalyst; Heck Reaction; Schlenk technique;98%
With trans-Pd(OAc)2(2,5-Mes2py)2; oxygen; acetic anhydride at 60℃; for 6h;74%
With 3,5-bis(trifluoromethyl)pyridin-2(1H)-one; silver(I) acetate; palladium diacetate In chloroform at 100℃; for 24h; Sealed tube; regioselective reaction;64%
[bis(acetoxy)iodo]benzene
3240-34-4

[bis(acetoxy)iodo]benzene

ethyl acrylate
140-88-5

ethyl acrylate

ethyl 3-phenyl-2-propenoate
103-36-6

ethyl 3-phenyl-2-propenoate

Conditions
ConditionsYield
With palladium diacetate; potassium carbonate In PEG-400 at 40℃; for 18h; Heck type coupling reaction; under air;98%
ethanol
64-17-5

ethanol

3-phenyl-propenal
104-55-2

3-phenyl-propenal

ethyl 3-phenyl-2-propenoate
103-36-6

ethyl 3-phenyl-2-propenoate

Conditions
ConditionsYield
With dihydrogen peroxide at 20℃; for 20h;98%
Stage #1: ethanol; 3-phenyl-propenal With tris(pentafluorophenyl)borate for 0.25h; Green chemistry;
Stage #2: With tert.-butylhydroperoxide In decane for 28h; Green chemistry;
87%
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; 1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene In toluene at 100℃; for 4h; Inert atmosphere;86%
With dihydrogen peroxide at 60℃; for 3h;
benzenediazonium tetrafluoroborate
369-57-3

benzenediazonium tetrafluoroborate

ethyl acrylate
140-88-5

ethyl acrylate

ethyl 3-phenyl-2-propenoate
103-36-6

ethyl 3-phenyl-2-propenoate

Conditions
ConditionsYield
With polystyrene resin supported theophylline carbene PdI2 complex In ethanol at 25℃; for 1h; Catalytic behavior; Reagent/catalyst; Temperature; Green chemistry;98%
With palladium diacetate In water at 20℃; for 16h; Catalytic behavior; Reagent/catalyst; Heck Reaction;88%
In water at 40℃; for 4h;81%
ethyl 2,3-dibromo-3-phenylpropanoate
99570-23-7

ethyl 2,3-dibromo-3-phenylpropanoate

ethyl 3-phenyl-2-propenoate
103-36-6

ethyl 3-phenyl-2-propenoate

Conditions
ConditionsYield
With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; sodium carbonate In dimethyl sulfoxide at 20℃; for 1.5h; Inert atmosphere; Irradiation;98%
4,4'-dimethylbenzoin
1218-89-9

4,4'-dimethylbenzoin

A

ethyl 3-phenyl-2-propenoate
103-36-6

ethyl 3-phenyl-2-propenoate

B

1,2-di(4-methylphenyl)-1,2-ethanedione
3457-48-5

1,2-di(4-methylphenyl)-1,2-ethanedione

Conditions
ConditionsYield
With 2,6-dimethylpyridine; 2,3-dibromo-3-phenyl-propionic acid ethyl ester; triphenylantimony dibromide In chloroform-d1 at 70℃; for 72h;A 95%
B 97%
(1S,2R)-1,2-diphenylethane-1,2-diol
579-43-1

(1S,2R)-1,2-diphenylethane-1,2-diol

ethyl (triphenylphosphoranylidene)acetate
1099-45-2

ethyl (triphenylphosphoranylidene)acetate

ethyl 3-phenyl-2-propenoate
103-36-6

ethyl 3-phenyl-2-propenoate

Conditions
ConditionsYield
With manganese(IV) oxide In dichloromethane at 20℃; for 3h; oxidative cleavage-Wittig process;97%
diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

benzaldehyde
100-52-7

benzaldehyde

ethyl 3-phenyl-2-propenoate
103-36-6

ethyl 3-phenyl-2-propenoate

Conditions
ConditionsYield
With triphenylphosphine; ruthenium-salen complex In toluene at 60℃; for 3h;97%
With triphenylphosphine; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate; meso-tetrakis(tetraphenyl)porphyrin iron(III) chloride In dichloromethane at 80℃; for 1h;91%
With meso-tetraphenylporphyrin iron(III) chloride; triphenylphosphine In toluene at 80℃; Inert atmosphere;89%
ethyl 4-bromocinnamate
24393-53-1, 136265-11-7, 15795-20-7

ethyl 4-bromocinnamate

ethyl 3-phenyl-2-propenoate
103-36-6

ethyl 3-phenyl-2-propenoate

Conditions
ConditionsYield
Stage #1: ethyl 4-bromocinnamate With dichloro[1,1′-bis[bis(1,1-dimethylethyl)phosphino]ferrocene-P,P′]palladium; triethylamine In water at 20℃; for 0.0333333h;
Stage #2: With 1,1,3,3-Tetramethyldisiloxane for 0.05h;
97%
diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

benzaldehyde
100-52-7

benzaldehyde

ethyl 3-phenyl-2-propenoate
103-36-6

ethyl 3-phenyl-2-propenoate

Conditions
ConditionsYield
With triethylamine; lithium bromide In tetrahydrofuran at 25℃; for 3h;96%
With potassium fluoride; tetrabutyl-ammonium chloride In acetonitrile at 100℃; for 24h;83%
With aluminum oxide; potassium fluoride at 20℃; for 18h;76%
benzaldehyde
100-52-7

benzaldehyde

Merrifield resin-bound-2,3,5,6-tetrafluorophenyl-ethyl(pentafluoropropyl)phosphonoacetate

Merrifield resin-bound-2,3,5,6-tetrafluorophenyl-ethyl(pentafluoropropyl)phosphonoacetate

ethyl 3-phenyl-2-propenoate
103-36-6

ethyl 3-phenyl-2-propenoate

Conditions
ConditionsYield
Stage #1: Merrifield resin-bound-2,3,5,6-tetrafluorophenyl-ethyl(pentafluoropropyl)phosphonoacetate With sodium hydride In tetrahydrofuran at 25℃; for 1h; Horner-Wadsworth-Emmons olefination;
Stage #2: benzaldehyde With sodium hydride In tetrahydrofuran at 25℃; for 14h; Further stages.;
96%
Cinnamic acid
621-82-9

Cinnamic acid

ethyl 3-phenyl-2-propenoate
103-36-6

ethyl 3-phenyl-2-propenoate

Conditions
ConditionsYield
With polyaniline-sulfate salt In ethanol for 24h; Heating / reflux;95%
ethyl trifluoroacetate,
383-63-1

ethyl trifluoroacetate,

1,4-diphenyl-3-butene-2-one
5409-59-6

1,4-diphenyl-3-butene-2-one

A

ethyl 3-phenyl-2-propenoate
103-36-6

ethyl 3-phenyl-2-propenoate

B

1,1,1-Trifluoro-3-phenylpropan-2-one
350-92-5

1,1,1-Trifluoro-3-phenylpropan-2-one

Conditions
ConditionsYield
Stage #1: ethyl trifluoroacetate, With sodium hydride In tetrahydrofuran at 20℃; for 0.166667h; Inert atmosphere; Schlenk technique;
Stage #2: 1,4-diphenyl-3-butene-2-one In tetrahydrofuran at 0℃; for 5h; Inert atmosphere; Schlenk technique; Reflux;
Stage #3: With hydrogenchloride In tetrahydrofuran; water at 0℃; for 0.25h; Inert atmosphere; Schlenk technique;
A 94%
B 95%
ethanol
64-17-5

ethanol

N,N-di(pyridin-2-yl)cinnamamide

N,N-di(pyridin-2-yl)cinnamamide

ethyl 3-phenyl-2-propenoate
103-36-6

ethyl 3-phenyl-2-propenoate

Conditions
ConditionsYield
With zinc trifluoromethanesulfonate at 20℃; Glovebox; Inert atmosphere; Solvolysis;95%
ethanol
64-17-5

ethanol

3-Phenylpropenol
104-54-1

3-Phenylpropenol

A

ethyl 3-phenyl-2-propenoate
103-36-6

ethyl 3-phenyl-2-propenoate

B

3-Phenyl-1-propanol
122-97-4

3-Phenyl-1-propanol

Conditions
ConditionsYield
With oxygen; potassium hydroxide In chloroform; water at 35℃; under 760.051 Torr; for 5h; Kinetics;A 94%
B 6%
benzaldehyde
100-52-7

benzaldehyde

ethyl bromoacetate
105-36-2

ethyl bromoacetate

ethyl 3-phenyl-2-propenoate
103-36-6

ethyl 3-phenyl-2-propenoate

Conditions
ConditionsYield
With sodium hydrogencarbonate; triphenylphosphine at 20℃; for 2h; Wittig reaction;93%
With disodium telluride In tetrahydrofuran at -20℃;60%
With 2,6-bis(3,4,5-trimethoxyphenyl)-[1,3,2]oxazaphospholo[2,3-b][1,3,2]oxazaphosphole; potassium carbonate In toluene at 50℃; for 12h; Reagent/catalyst; Temperature; Solvent; Wittig Olefination;57%
With cadmium 1.) glyme, 20 deg C, 2.) diethyl ether, reflux, 24 h; Yield given. Multistep reaction;
benzaldehyde
100-52-7

benzaldehyde

ethyl (triphenylphosphoranylidene)acetate
1099-45-2

ethyl (triphenylphosphoranylidene)acetate

ethyl 3-phenyl-2-propenoate
103-36-6

ethyl 3-phenyl-2-propenoate

Conditions
ConditionsYield
In water at 27℃; for 1.5h; Wittig reaction;93%
In water at 24.99℃; for 3h; Kinetics; Wittig reaction;92%
In ethanol Reflux;90%
ethyl acrylate
140-88-5

ethyl acrylate

phenylboronic acid
98-80-6

phenylboronic acid

ethyl 3-phenyl-2-propenoate
103-36-6

ethyl 3-phenyl-2-propenoate

Conditions
ConditionsYield
With polyaniline supported palladium In acetonitrile at 80℃; for 4h; Heck reaction; under air;93%
With 1,10-Phenanthroline In water; toluene at 110℃; for 3h; Heck Reaction;89%
With C16H14N2O4Pd; silver(I) acetate In 1-methyl-pyrrolidin-2-one at 90℃; for 6h;72%
With tert-butyl-amphos chloride; sodium dodecyl-sulfate; sodium carbonate; norborn-2-ene; chloro(1,5-cyclooctadiene)rhodium(I) dimer In water; toluene at 80℃;
With SBA-Rh In water; toluene at 100℃; for 3h; Heck reaction; Inert atmosphere;89 %Chromat.
ethanol
64-17-5

ethanol

3-Phenylpropenol
104-54-1

3-Phenylpropenol

ethyl 3-phenyl-2-propenoate
103-36-6

ethyl 3-phenyl-2-propenoate

Conditions
ConditionsYield
With dihydrogen peroxide for 3h; Irradiation;93%
With Au/CeO2; oxygen; caesium carbonate at 30℃; under 760.051 Torr; for 48h; Reagent/catalyst;
iodobenzene
591-50-4

iodobenzene

acrylic acid methyl ester
292638-85-8

acrylic acid methyl ester

ethyl 3-phenyl-2-propenoate
103-36-6

ethyl 3-phenyl-2-propenoate

Conditions
ConditionsYield
With potassium phosphate at 40℃; for 1h; Catalytic behavior; Heck Reaction;93%
hydrogen ethyl malonate
1071-46-1

hydrogen ethyl malonate

S-phenyl ethyl ammoniumacetate
72190-33-1

S-phenyl ethyl ammoniumacetate

benzaldehyde
100-52-7

benzaldehyde

A

ethyl 3-phenyl-2-propenoate
103-36-6

ethyl 3-phenyl-2-propenoate

B

ethyl N-[(S)-α-methylbenzyl]-β-amino-β-phenylpropionate

ethyl N-[(S)-α-methylbenzyl]-β-amino-β-phenylpropionate

Conditions
ConditionsYield
With NCI-88947 In ethanol for 10h; Heating;A 92%
B 4%
for 0.166667h; Rodionov reaction; Irradiation;A 67%
B 19%
Triethyl orthoacetate
78-39-7

Triethyl orthoacetate

Cinnamic acid
621-82-9

Cinnamic acid

ethyl 3-phenyl-2-propenoate
103-36-6

ethyl 3-phenyl-2-propenoate

Conditions
ConditionsYield
microwave irradiation;92%
3-ethoxy-1-phenyl-prop-2-yn-1-ol
99865-03-9

3-ethoxy-1-phenyl-prop-2-yn-1-ol

ethyl 3-phenyl-2-propenoate
103-36-6

ethyl 3-phenyl-2-propenoate

Conditions
ConditionsYield
With ethanol; camphor-10-sulfonic acid; silver hexafluoroantimonate; gold(I) chloride In tetrahydrofuran; dichloromethane at 20℃; Meyer-Schuster reaction;92%
With boron trifluoride diethyl etherate In 1,4-dioxane; ethanol at 20℃; Meyer-Schuster Rearrangement; Inert atmosphere;55%
diethyl benzalmalonate
5292-53-5

diethyl benzalmalonate

ethyl 3-phenyl-2-propenoate
103-36-6

ethyl 3-phenyl-2-propenoate

Conditions
ConditionsYield
With stearic acid; tetrabutyl phosphonium bromide at 200℃; for 16h;91%
chlorobenzene
108-90-7

chlorobenzene

ethyl acrylate
140-88-5

ethyl acrylate

ethyl 3-phenyl-2-propenoate
103-36-6

ethyl 3-phenyl-2-propenoate

Conditions
ConditionsYield
With C128H58Cl2O2P4Pd; potassium carbonate In methanol at 60℃; Reagent/catalyst; Heck Reaction; Inert atmosphere; Schlenk technique;91%
With [Pd(3-((1-ethyl-1H-benzimidazol-2-yl)methyl)-1-((6-methylpyridin-2-yl)-methyl)benzimidazolylidene)2](PF6)2; potassium carbonate In N,N-dimethyl-formamide at 100℃; for 24h; Inert atmosphere; Schlenk technique;90%
With C34H29Br3OP2Pd; potassium carbonate In N,N-dimethyl-formamide at 130℃; for 6h; Catalytic behavior; Reagent/catalyst; Heck Reaction; Inert atmosphere; Schlenk technique;88%
ethyl 3-phenyl-2-propenoate
103-36-6

ethyl 3-phenyl-2-propenoate

ethyl dihydrocinnamate
2021-28-5

ethyl dihydrocinnamate

Conditions
ConditionsYield
With cyclohexene In ethanol at 70℃; for 14h; Inert atmosphere;100%
With hydrogen; polysilane-supported palladium In hexane at 20℃; for 2h;100%
With hydrogen In neat (no solvent) at 50℃; for 5h; Catalytic behavior; Temperature; Flow reactor;100%
ethyl 3-phenyl-2-propenoate
103-36-6

ethyl 3-phenyl-2-propenoate

2,3-dibromo-3-phenyl-propionic acid ethyl ester
5464-70-0

2,3-dibromo-3-phenyl-propionic acid ethyl ester

Conditions
ConditionsYield
With bromine In various solvent(s) for 1h; Ambient temperature;100%
With tetrachloromethane; bromine
With bromine inactive substance;
ethyl 3-phenyl-2-propenoate
103-36-6

ethyl 3-phenyl-2-propenoate

ethyl 3-phenylglycidate
121-39-1

ethyl 3-phenylglycidate

Conditions
ConditionsYield
With 3,3-dimethyldioxirane In acetone at 20℃; for 24h;100%
With dihydrogen peroxide; acetic acid In acetonitrile for 1h; enantioselective reaction;92%
With water; fluorine In acetonitrile for 0.0166667h;80%
ethyl 3-phenyl-2-propenoate
103-36-6

ethyl 3-phenyl-2-propenoate

3-Phenylpropenol
104-54-1

3-Phenylpropenol

3-phenyl-2-propen-1-yl 3-phenylacrylate
40918-97-6, 61019-10-1, 122-69-0

3-phenyl-2-propen-1-yl 3-phenylacrylate

Conditions
ConditionsYield
[Cl(C6F13C2H4)2SnOSn(C2H4C6F13)2Cl]2 In toluene at 150℃; for 16h;100%
ethyl 3-phenyl-2-propenoate
103-36-6

ethyl 3-phenyl-2-propenoate

benzyl alcohol
100-51-6

benzyl alcohol

benzy cinnamate
103-41-3

benzy cinnamate

Conditions
ConditionsYield
[Cl(C6F13C2H4)2SnOSn(C2H4C6F13)2Cl]2 In toluene at 150℃; for 16h;100%
ethyl 3-phenyl-2-propenoate
103-36-6

ethyl 3-phenyl-2-propenoate

3-Phenylpropenol
104-54-1

3-Phenylpropenol

A

ethanol
64-17-5

ethanol

B

3-phenyl-2-propen-1-yl 3-phenylacrylate
40918-97-6, 61019-10-1, 122-69-0

3-phenyl-2-propen-1-yl 3-phenylacrylate

Conditions
ConditionsYield
2[{Cl(C6F13CH2CH2)2SnOSn(CH2CH2C6F13)2Cl}2] In various solvent(s) at 150℃; for 16h;A n/a
B 99%
ethyl 3-phenyl-2-propenoate
103-36-6

ethyl 3-phenyl-2-propenoate

3-Phenylpropenol
104-54-1

3-Phenylpropenol

Conditions
ConditionsYield
Stage #1: ethyl 3-phenyl-2-propenoate With C48H62ErN7O2Si2; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In toluene at 110℃; for 6h; Inert atmosphere;
Stage #2: With silica gel In methanol at 60℃; for 3h; Inert atmosphere;
99%
With bis(acetylacetonato)dioxidomolybdenum(VI); 1,1,3,3-Tetramethyldisiloxane; Triphenylphosphine oxide In toluene at 100℃; for 72h; Inert atmosphere; Sealed tube;82%
With potassium borohydride; lithium chloride for 0.0833333h; microwave irradiation;55 % Chromat.
ethyl 3-phenyl-2-propenoate
103-36-6

ethyl 3-phenyl-2-propenoate

cinnamamide
621-79-4

cinnamamide

Conditions
ConditionsYield
With magnesium nitride In methanol at 80℃; for 24h;99%
With ammonium chloride; magnesium methanolate In methanol at 80℃; for 24h; Inert atmosphere;87%
With ammonia; calcium chloride In methanol at 80℃; under 1275.13 Torr; for 24h; Inert atmosphere;85%
ethyl 3-phenyl-2-propenoate
103-36-6

ethyl 3-phenyl-2-propenoate

ethyl 3-phenylpropanoate-α,β-d2

ethyl 3-phenylpropanoate-α,β-d2

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen chloride; zinc In water-d2 at 20℃;98%
With water-d2 for 6h; Milling; Green chemistry;98%
Stage #1: ethyl 3-phenyl-2-propenoate With samarium diiodide In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere;
Stage #2: With water-d2 In tetrahydrofuran Inert atmosphere;
93%
ethyl 3-phenyl-2-propenoate
103-36-6

ethyl 3-phenyl-2-propenoate

acetic anhydride
108-24-7

acetic anhydride

syn-3-ethoxy-3-oxo-1-phenylpropane-1,2-diyl diacetate

syn-3-ethoxy-3-oxo-1-phenylpropane-1,2-diyl diacetate

Conditions
ConditionsYield
Stage #1: ethyl 3-phenyl-2-propenoate With 4-tolyl iodide; boron trifluoride diethyl etherate; water; 3-chloro-benzenecarboperoxoic acid In acetic acid at 20℃; for 48h;
Stage #2: acetic anhydride In acetic acid at 20℃; optical yield given as %de; diastereoselective reaction;
98%
ethyl 3-phenyl-2-propenoate
103-36-6

ethyl 3-phenyl-2-propenoate

aniline
62-53-3

aniline

4-phenyl-2-quinolinone
5855-57-2

4-phenyl-2-quinolinone

Conditions
ConditionsYield
Stage #1: aniline With acetic anhydride In toluene at 20℃; for 0.0833333h; Schlenk technique; Inert atmosphere;
Stage #2: ethyl 3-phenyl-2-propenoate With sodium persulfate; palladium diacetate; toluene-4-sulfonic acid In toluene at 100℃; for 36h; Schlenk technique; Inert atmosphere;
98%
ethyl 3-phenyl-2-propenoate
103-36-6

ethyl 3-phenyl-2-propenoate

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

ethyl dihydrocinnamate
2021-28-5

ethyl dihydrocinnamate

Conditions
ConditionsYield
With methanol; copper(l) iodide; caesium carbonate In tetrahydrofuran at 20℃; for 30h; Inert atmosphere; chemoselective reaction;98%
ethyl 3-phenyl-2-propenoate
103-36-6

ethyl 3-phenyl-2-propenoate

lithium dimethylcuprate
15681-48-8

lithium dimethylcuprate

Conditions
ConditionsYield
With chloro-trimethyl-silane In diethyl ether for 2h; -78 deg C to 20 deg C;97%
In diethyl ether Product distribution; -78 deg C to 20 deg C, 2h; with and without addition of Me3SiCl;
ethyl 3-phenyl-2-propenoate
103-36-6

ethyl 3-phenyl-2-propenoate

Diphenylphosphine oxide
4559-70-0

Diphenylphosphine oxide

3-(Diphenyl-phosphinoyl)-3-phenyl-propionic acid ethyl ester
145290-30-8

3-(Diphenyl-phosphinoyl)-3-phenyl-propionic acid ethyl ester

Conditions
ConditionsYield
With potassium hydroxide; potassium carbonate In benzene for 0.25h; Ambient temperature;97%
With (1S,2S)-1,2-Cy[NC(Me)CHC(Me)N(2,6-Et2C6H3)]2YN(SiMe3)2 In toluene at 20℃; for 1h; Schlenk technique; Inert atmosphere; regioselective reaction;95%
methanol
67-56-1

methanol

ethyl 3-phenyl-2-propenoate
103-36-6

ethyl 3-phenyl-2-propenoate

methyl cinnamate
103-26-4

methyl cinnamate

Conditions
ConditionsYield
scandium tris(trifluoromethanesulfonate) at 64℃; for 65h;97%
With sodium methylate at 60℃;88.1%

Ethyl cinnamate Chemical Properties

Molecular Structure of Ethyl 3-phenyl propenoate (CAS NO.103-36-6):

IUPAC Name: ethyl (E)-3-phenylprop-2-enoate 
Empirical Formula: C11H12O2
Molecular Weight: 176.2118
H bond acceptors: 2
H bond donors: 0
Freely Rotating Bonds: 4
Polar Surface Area: 26.3 Å2
Index of Refraction: 1.55
Molar Refractivity: 53.18 cm3
Molar Volume: 166.9 cm3
Surface Tension: 38 dyne/cm
Density: 1.055 g/cm3
Flash Point: 148.6 °C
Enthalpy of Vaporization: 50.75 kJ/mol
Boiling Point: 269.3 °C at 760 mmHg
Vapour Pressure: 0.00729 mmHg at 25°C
Melting point: 6-8 °C(lit.)
Storage temp: Refrigerator (+4°C)
Water Solubility: insoluble
Merck: 14,2299
BRN: 1238804
InChI
InChI=1/C11H12O2/c1-2-13-11(12)9-8-10-6-4-3-5-7-10/h3-9H,2H2,1H3/b9-8+
Smiles
c1(\C=C\C(OCC)=O)ccccc1
EINECS: 203-104-6
Product Categories: Aromatic Cinnamic Acids, Esters and Derivatives; Alphabetical Listings; Certified Natural ProductsFlavors and Fragrances; E-F; Flavors and Fragrances; C10 to C11; Carbonyl Compounds; Esters

Ethyl cinnamate Uses

 Ethyl 3-phenyl propenoate (CAS NO.103-36-6) is  the important intermediates of  flavor, also can be used in medicine, food additive intermediates.

Ethyl cinnamate Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 oral 4gm/kg (4000mg/kg)   Voprosy Pitaniya. Problems of Nutrition. Vol. 33(5), Pg. 48, 1974.
mouse LD50 oral 4gm/kg (4000mg/kg)   Voprosy Pitaniya. Problems of Nutrition. Vol. 33(5), Pg. 48, 1974.
rabbit LD50 skin > 5gm/kg (5000mg/kg)   Food and Cosmetics Toxicology. Vol. 12, Pg. 719, 1974.
rat LD50 oral 4gm/kg (4000mg/kg)   Voprosy Pitaniya. Problems of Nutrition. Vol. 33(5), Pg. 48, 1974.

Ethyl cinnamate Consensus Reports

Reported in EPA TSCA Inventory.

Ethyl cinnamate Safety Profile

Moderately toxic by ingestion. Combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes. See also ESTERS.
Risk Statements: 20-22
R20:Harmful by inhalation. 
R22:Harmful if swallowed.
Safety Statements: 23-24/25
S23:Do not breathe vapour. 
S24/25:Avoid contact with skin and eyes.
WGK Germany: 1
RTECS: GD9010000

Ethyl cinnamate Specification

  Ethyl 3-phenyl propenoate , with CAS number of 103-36-6, can be called (2E)-3-Phénylacrylate d'éthyle ; (Z)-Ethyl cinnamate ; 2-propenoic acid, 3-phenyl-, ethyl ester ; 2-propenoic acid, 3-phenyl-, ethyl ester, (2E)- ; 2-Propenoic acid, 3-phenyl-, ethyl ester, (E)- ; Ethyl (2E)-3-phenyl-2-propenoate ; Ethyl (2E)-3-phenylacrylate ; ethyl (2E)-3-phenylprop-2-enoate . It is a colourless liquid.

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