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Ethyl cinnamate

  • Name Ethyl cinnamate
  • EINECS203-104-6
  • CAS No. 103-36-6
  • Density1.055 g/cm3
  • PSA26.30000
  • LogP2.26290
  • Solubilityinsoluble in water
  • Melting Point6-8 °C(lit.)
  • FormulaC11H12O2
  • Boiling Point269.3 °C at 760 mmHg
  • Molecular Weight176.215
  • Flash Point148.6 °C
  • Transport InformationN/A
  • Appearancecolorless liquid
  • Safety23-24/25
  • Risk Codes20-22
  • Molecular Structure
    Molecular Structure of 103-36-6 (Ethyl cinnamate)
  • Hazard SymbolsN/A
  • SynonymsN/A
  • Article Data384

Ethyl cinnamate Synthetic route

591-50-4

iodobenzene

140-88-5

ethyl acrylate

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%
2216-94-6

phenylpropynoic acid ethyl ester

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;
108-86-1

bromobenzene

140-88-5

ethyl acrylate

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%
5464-70-0

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

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%
64-17-5

ethanol

621-82-9

Cinnamic acid

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%
140-88-5

ethyl acrylate

71-43-2

benzene

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%
3240-34-4

[bis(acetoxy)iodo]benzene

140-88-5

ethyl acrylate

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%
64-17-5

ethanol

104-55-2

3-phenyl-propenal

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;
369-57-3

benzenediazonium tetrafluoroborate

140-88-5

ethyl acrylate

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%
99570-23-7

ethyl 2,3-dibromo-3-phenylpropanoate

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%

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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