Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With palladium diacetate; potassium carbonate In PEG-400 at 40℃; for 18h; Heck type coupling reaction; under air; | 98% |
Conditions | Yield |
---|---|
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
ethyl acrylate
ethyl 3-phenyl-2-propenoate
Conditions | Yield |
---|---|
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
ethyl 3-phenyl-2-propenoate
Conditions | Yield |
---|---|
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
A
ethyl 3-phenyl-2-propenoate
B
1,2-di(4-methylphenyl)-1,2-ethanedione
Conditions | Yield |
---|---|
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
ethyl (triphenylphosphoranylidene)acetate
ethyl 3-phenyl-2-propenoate
Conditions | Yield |
---|---|
With manganese(IV) oxide In dichloromethane at 20℃; for 3h; oxidative cleavage-Wittig process; | 97% |
Conditions | Yield |
---|---|
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
ethyl 3-phenyl-2-propenoate
Conditions | Yield |
---|---|
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
benzaldehyde
ethyl 3-phenyl-2-propenoate
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With polyaniline-sulfate salt In ethanol for 24h; Heating / reflux; | 95% |
ethyl trifluoroacetate,
1,4-diphenyl-3-butene-2-one
A
ethyl 3-phenyl-2-propenoate
B
1,1,1-Trifluoro-3-phenylpropan-2-one
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With zinc trifluoromethanesulfonate at 20℃; Glovebox; Inert atmosphere; Solvolysis; | 95% |
ethanol
3-Phenylpropenol
A
ethyl 3-phenyl-2-propenoate
B
3-Phenyl-1-propanol
Conditions | Yield |
---|---|
With oxygen; potassium hydroxide In chloroform; water at 35℃; under 760.051 Torr; for 5h; Kinetics; | A 94% B 6% |
Conditions | Yield |
---|---|
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
ethyl (triphenylphosphoranylidene)acetate
ethyl 3-phenyl-2-propenoate
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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. |
Conditions | Yield |
---|---|
With dihydrogen peroxide for 3h; Irradiation; | 93% |
With Au/CeO2; oxygen; caesium carbonate at 30℃; under 760.051 Torr; for 48h; Reagent/catalyst; |
Conditions | Yield |
---|---|
With potassium phosphate at 40℃; for 1h; Catalytic behavior; Heck Reaction; | 93% |
hydrogen ethyl malonate
S-phenyl ethyl ammoniumacetate
benzaldehyde
A
ethyl 3-phenyl-2-propenoate
Conditions | Yield |
---|---|
With NCI-88947 In ethanol for 10h; Heating; | A 92% B 4% |
for 0.166667h; Rodionov reaction; Irradiation; | A 67% B 19% |
Conditions | Yield |
---|---|
microwave irradiation; | 92% |
3-ethoxy-1-phenyl-prop-2-yn-1-ol
ethyl 3-phenyl-2-propenoate
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With stearic acid; tetrabutyl phosphonium bromide at 200℃; for 16h; | 91% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With bromine In various solvent(s) for 1h; Ambient temperature; | 100% |
With tetrachloromethane; bromine | |
With bromine inactive substance; |
Conditions | Yield |
---|---|
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
3-Phenylpropenol
3-phenyl-2-propen-1-yl 3-phenylacrylate
Conditions | Yield |
---|---|
[Cl(C6F13C2H4)2SnOSn(C2H4C6F13)2Cl]2 In toluene at 150℃; for 16h; | 100% |
Conditions | Yield |
---|---|
[Cl(C6F13C2H4)2SnOSn(C2H4C6F13)2Cl]2 In toluene at 150℃; for 16h; | 100% |
ethyl 3-phenyl-2-propenoate
3-Phenylpropenol
A
ethanol
B
3-phenyl-2-propen-1-yl 3-phenylacrylate
Conditions | Yield |
---|---|
2[{Cl(C6F13CH2CH2)2SnOSn(CH2CH2C6F13)2Cl}2] In various solvent(s) at 150℃; for 16h; | A n/a B 99% |
Conditions | Yield |
---|---|
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. |
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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
bis(pinacol)diborane
ethyl dihydrocinnamate
Conditions | Yield |
---|---|
With methanol; copper(l) iodide; caesium carbonate In tetrahydrofuran at 20℃; for 30h; Inert atmosphere; chemoselective reaction; | 98% |
ethyl 3-phenyl-2-propenoate
lithium dimethylcuprate
ethyl 3-phenylbutanoate
Conditions | Yield |
---|---|
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
Diphenylphosphine oxide
3-(Diphenyl-phosphinoyl)-3-phenyl-propionic acid ethyl ester
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
scandium tris(trifluoromethanesulfonate) at 64℃; for 65h; | 97% |
With sodium methylate at 60℃; | 88.1% |
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 3-phenyl propenoate (CAS NO.103-36-6) is the important intermediates of flavor, also can be used in medicine, food additive intermediates.
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. |
Reported in EPA TSCA Inventory.
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 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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