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103-41-3

Basic Information
CAS No.: 103-41-3
Name: Benzyl cinnamate
Article Data: 164
Molecular Structure:
Molecular Structure of 103-41-3 (Benzyl cinnamate)
Formula: C16H14O2
Molecular Weight: 238.286
Synonyms: Cinnamicacid, benzyl ester (6CI,7CI,8CI);3-Phenyl-2-propenoic acid benzyl ester;Benzyl 3-phenylpropenoate;Benzyl g-phenylacrylate;Cinnamein;NSC 11780;NSC 44403;
EINECS: 203-109-3
Density: 1.128 g/cm3
Melting Point: 34-37 °C(lit.)
Boiling Point: 371.2 °C at 760 mmHg
Flash Point: 225.7 °C
Solubility: PRACTICALLY INSOLUBLE
Appearance: clear colorless to yellowish crystalline
Risk Codes: 36/37/38
Safety: 22-24/25
Transport Information: UN 3077
PSA: 26.30000
LogP: 3.44320
Synthetic route
140-11-4

Benzyl acetate

100-52-7

benzaldehyde

103-41-3

(E)-cinnamic acid benzyl ester

Conditions
ConditionsYield
With titanium tetrachloride; triethylamine In dichloromethane at 0 - 25℃; Inert atmosphere; stereoselective reaction;99%
With iodine; magnesium; mercury dichloride Reagens 4: Xylol;
38986-89-9

trans-cinnamoyl fluoride

100-51-6

benzyl alcohol

103-41-3

(E)-cinnamic acid benzyl ester

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃;99%
20194-18-7

sodium phenyl-methanolate

103-41-3

(E)-cinnamic acid benzyl ester

Conditions
ConditionsYield
In tetrahydrofuran Ambient temperature;98%
591-50-4

iodobenzene

2495-35-4

benzylacrylate

103-41-3

(E)-cinnamic acid benzyl ester

Conditions
ConditionsYield
With C40H42N6O4Pd(2+)*2Br(1-); potassium carbonate In water at 80℃; for 4h; Reagent/catalyst; Heck Reaction;98%
With potassium carbonate; di(μ-acetato)-bis(7-fluoro-2,4,8-trimethylquinoline)Pd2 In N,N-dimethyl-formamide at 140℃; Heck reaction;
1399175-32-6

(E)-benzyl-3-(2-((E)-piperidin-1-yldiazenyl)phenyl)acrylate

103-41-3

(E)-cinnamic acid benzyl ester

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In 1,2-dimethoxyethane at 20℃; for 2h; Inert atmosphere;98%
103-26-4

Methyl cinnamate

100-51-6

benzyl alcohol

103-41-3

(E)-cinnamic acid benzyl ester

Conditions
ConditionsYield
With N,N'-biscyclohexyl-imidazol-2-ylidene; 4 A molecular sieve In tetrahydrofuran at 20℃; for 3h;97%
1,3-dicyclohexyl-imidazol-2-ylidene In tetrahydrofuran at 20℃; for 3h;97%
With iron(III)-acetylacetonate In n-heptane at 105℃; for 10h; Inert atmosphere;96%
140-10-3

(E)-3-phenylacrylic acid

100-39-0

benzyl bromide

103-41-3

(E)-cinnamic acid benzyl ester

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 0.75h; Esterification;97%
Stage #1: (E)-3-phenylacrylic acid With caesium carbonate In methanol; water at 0℃; pH=7;
Stage #2: benzyl bromide In N,N-dimethyl-formamide at 20℃; for 16h;
96%
With potassium carbonate In acetonitrile for 8h; Reflux;94%
With potassium fluoride; tetra(n-butyl)ammonium hydrogensulfate In tetrahydrofuran at 20℃; for 6h;85%
40204-26-0

malonic acid monobenzyl ester

100-52-7

benzaldehyde

103-41-3

(E)-cinnamic acid benzyl ester

Conditions
ConditionsYield
With piperidine; dmap In N,N-dimethyl-formamide at 25℃; Doebner-Knoevenagel reaction;96%
With dmap In N,N-dimethyl-formamide at 25℃; Knoevenagel reaction;96%
O-benzyl-N-cyclohexyl-N\-methylpolystyrene isourea

O-benzyl-N-cyclohexyl-N\-methylpolystyrene isourea

140-10-3

(E)-3-phenylacrylic acid

103-41-3

(E)-cinnamic acid benzyl ester

Conditions
ConditionsYield
In acetonitrile at 125℃; for 0.05h; microwave irradiation;96%
1071-46-1

hydrogen ethyl malonate

100-52-7

benzaldehyde

103-41-3

(E)-cinnamic acid benzyl ester

Conditions
ConditionsYield
dmap In N,N-dimethyl-formamide at 20℃; for 5h;96%
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  • Benzyl cinnamate

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    103-41-3

    Benzyl cinnamate

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    Name Benzyl cinnamate Synonyms Phenylmethyl 3-phenylprop-2-enoate CAS Registry Number 103-41-3 EINECS 203-109-3 Appearance:Colorless

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    Benzyl cinnamate

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  • Benzyl cinnamate CAS NO.103-41-3

  • Casno:

    103-41-3

    Benzyl cinnamate CAS NO.103-41-3

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  • Benzyl cinnamate CAS NO.103-41-3

  • Casno:

    103-41-3

    Benzyl cinnamate CAS NO.103-41-3

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  • Cinnamic Acid-Benzyl Ester

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    103-41-3

    Benzyl cinnamate

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  • 103-41-3  CAS NO.103-41-3

  • Casno:

    103-41-3

    103-41-3 CAS NO.103-41-3

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  • Benzyl cinnamate CAS NO.103-41-3

  • Casno:

    103-41-3

    Benzyl cinnamate CAS NO.103-41-3

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  • Benzyl cinnaMate

  • Casno:

    103-41-3

    Benzyl cinnaMate

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    Product Name: Benzyl cinnamate Synonyms: 2-Propenoic acid, 3-phenyl-, phenylmethyl ester;2-Propenoicacid,3-phenyl-,phenylmethylester;3-Phenyl-2-propenoic acid phenylmethyl ester;3-phenyl-2-propenoicacidphenylmethylester;3-phenyl-2-propenoicaciphen

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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

The Benzyl cinnamate, with is CAS registry number 103-41-3, has the IUPAC name of benzyl (E)-3-phenylprop-2-enoate. For being a kind of clear colorless to yellowish crystalline, it is practically insoluble, and its product categories are including Fine Chemical & Intermediates; Cinnamic acid. Besides, it is used in the application of artificial flavors, and perfumes.

The characteristics of this chemical are as below: (1)ACD/LogP: 3.65; (2)# of Rule of 5 Violations: 0; (3)#H bond acceptors: 2; (4)#H bond donors: 0; (5)#Freely Rotating Bonds: 5; (6)Polar Surface Area: 26.3; (7)Index of Refraction: 1.608; (8)Molar Refractivity: 73.03 cm3; (9)Molar Volume: 211 cm3; (10)Polarizability: 28.95×10-24 cm3; (11)Surface Tension: 45 dyne/cm; (12)Density: 1.128 g/cm3; (13)Flash Point: 225.7 °C; (14)Enthalpy of Vaporization: 61.82 kJ/mol; (15)Boiling Point: 371.2 °C at 760 mmHg; (16)Vapour Pressure: 1.05E-05 mmHg at 25°C; (17)Exact Mass: 238.09938; (18)MonoIsotopic Mass: 238.09938; (19)Topological Polar Surface Area: 26.3; (20)Heavy Atom Count: 18; (21)Complexity: 271.

Production method of this chemical: phenylmethanol could react with 3-phenyl-acrylic acid ethyl ester to produce benzyl cinnamate. The reaction could happen in the presence of the analytic agent of [Cl(C6F13C2H4)2SnOSn(C2H4C6F13)2Cl]2 and the solvent of toluene. And it needs 16 hours to react with the yield of 100%.

When you are dealing with this chemical, you should be careful. This is irritating to eyes, respiratory system and skin, so you should avoid contacting with skin and eyes. And you should not breathe dust.

What's more, the following datas could be converted into the molecular structure:
(1)Canonical SMILES: C1=CC=C(C=C1)COC(=O)C=CC2=CC=CC=C2
(2)Isomeric SMILES: C1=CC=C(C=C1)COC(=O)/C=C/C2=CC=CC=C2
(3)InChI: InChI=1S/C16H14O2/c17-16(12-11-14-7-3-1-4-8-14)18-13-15-9-5-2-6-10-15/h1-12H,13H2/b12-11+
(4)InChIKey: NGHOLYJTSCBCGC-VAWYXSNFSA-N 

Below are the toxicity information of this chemical:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 oral 3760mg/kg (3760mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

GASTROINTESTINAL: GASTRITIS
Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964.
rat LD50 oral 5530mg/kg (5530mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: COMA
Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964.