Benzyl cinnamate supplier | CasNO.103-41-3

Name
Benzyl cinnamate
EINECS 203-109-3
CAS No. 103-41-3
Article Data164
CAS DataBase
Density 1.128 g/cm³
Solubility PRACTICALLY INSOLUBLE
Melting Point 34-37 °C(lit.)
Formula C₁₆H₁₄O₂
Boiling Point 371.2 °C at 760 mmHg
Molecular Weight 238.286
Flash Point 225.7 °C
Transport Information UN 3077
Appearance clear colorless to yellowish crystalline
Safety 22-24/25
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols
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;
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

Conditions	Yield
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

Conditions	Yield
With triethylamine In dichloromethane at 20℃;	99%

: 100663-89-6, 105769-62-8, 106727-87-1
C21H16N2O2

: 20194-18-7
sodium phenyl-methanolate

: 103-41-3
(E)-cinnamic acid benzyl ester

Conditions

Conditions	Yield
In tetrahydrofuran Ambient temperature;	98%

: 591-50-4
iodobenzene

: 2495-35-4
benzylacrylate

: 103-41-3
(E)-cinnamic acid benzyl ester

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
dmap In N,N-dimethyl-formamide at 20℃; for 5h;	96%

: C24H19NO3

: 100-51-6
benzyl alcohol

: 103-41-3
(E)-cinnamic acid benzyl ester

Conditions

Conditions	Yield
With trimethylphosphane In dichloromethane; toluene at 20℃; for 3h;	96%

: 140-10-3
(E)-3-phenylacrylic acid

: 100-51-6
benzyl alcohol

: 103-41-3
(E)-cinnamic acid benzyl ester

Conditions

Conditions	Yield
With TiO(acac)2 In xylene for 12h; Heating;	95%
With 3-(5-nitro-2-oxo-1,2-dihydro-1-pyridyl)-1,2-benzisothiazole 1,1,-dioxide; triethylamine In dichloromethane -10 deg C -> r.t., overnight;	92%
tetrachlorobis(tetrahydrofuran)hafnium(IV) In toluene for 10h; Heating;	92%

: 18509-03-0
sodium trans-cinnamate

: 100-44-7
benzyl chloride

: 103-41-3
(E)-cinnamic acid benzyl ester

Conditions

Conditions	Yield
With 1,3-dimethylimidazolinium methanesulfonate at 90℃; for 0.5h;	95%

: 14371-10-9
(E)-3-phenylpropenal

: 100-51-6
benzyl alcohol

: 103-41-3
(E)-cinnamic acid benzyl ester

Conditions

Conditions	Yield
Stage #1: benzyl alcohol With 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,4-dimethyl-1,2,4-triazolium iodide; benzylamine In tetrahydrofuran for 0.0833333h; Inert atmosphere; Stage #2: (E)-3-phenylpropenal With 3,5,3',5'-tetra-tert-butyl-4,4'-diphenoquinone In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;	95%
With 4-methyl-3-(2,4,6-trimethylphenyl)thiazolium tetrafluoroborate; tetrabutylammomium bromide; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃; for 7h; Inert atmosphere; Electrochemical reaction;	83%
Stage #1: benzyl alcohol With 1,3-bis(2-(2-methoxyethyl)-6-methylphenyl)-1H-imidazol-3-ium perchlorate; 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: (E)-3-phenylpropenal With 1,1'-bis(4-oxo-3,5-di-t-butylcyclohexa)dienylidene In tetrahydrofuran at 20℃; for 2h; Reagent/catalyst; Inert atmosphere;	77 %Spectr.

: 140-10-3
(E)-3-phenylacrylic acid

: 5896-17-3
2-(phenylmethoxy)benzaldehyde

: 103-41-3
(E)-cinnamic acid benzyl ester

Conditions

Conditions	Yield
With 1-methyl-pyrrolidin-2-one; trifluorormethanesulfonic acid In chlorobenzene at 130℃; for 24h; Catalytic behavior; Mechanism; Reagent/catalyst; Solvent; Inert atmosphere; Schlenk technique;	95%

: 109299-93-6
3-((E)-3-phenyl-2-propenoyl)-1,3-oxazolidin-2-one

: 100-51-6
benzyl alcohol

: 103-41-3
(E)-cinnamic acid benzyl ester

Conditions

Conditions	Yield
With [t-Bu2SnCl(OH)]2 In toluene for 14h; Heating;	94%

: 140-10-3
(E)-3-phenylacrylic acid

: 31165-67-0
2'-benzyloxyacetophenone

: 103-41-3
(E)-cinnamic acid benzyl ester

Conditions

Conditions	Yield
With 1-methyl-pyrrolidin-2-one; trifluorormethanesulfonic acid In chlorobenzene at 130℃; for 24h; Inert atmosphere; Schlenk technique;	94%

: 140-10-3
(E)-3-phenylacrylic acid

: 10403-73-3
1,2-di(benzyloxy)benzene

: 103-41-3
(E)-cinnamic acid benzyl ester

Conditions

Conditions	Yield
With 1-methyl-pyrrolidin-2-one; trifluorormethanesulfonic acid In chlorobenzene at 130℃; for 24h; Inert atmosphere; Schlenk technique;	93%

: 100663-89-6, 105769-62-8, 106727-87-1
C21H16N2O2

: 100-51-6
benzyl alcohol

: 103-41-3
(E)-cinnamic acid benzyl ester

Conditions

Conditions	Yield
zinc(II) chloride In dichloromethane; acetonitrile for 18h; Ambient temperature;	92%

: 140-11-4
Benzyl acetate

: 103-26-4
Methyl cinnamate

: 103-41-3
(E)-cinnamic acid benzyl ester

Conditions

Conditions	Yield
With sodium 4-tert-butylphenolate; sodium t-butanolate In tetrahydrofuran	92%

: 2-benzyloxy-1-methylpyridinium triflate

: 140-10-3
(E)-3-phenylacrylic acid

: 103-41-3
(E)-cinnamic acid benzyl ester

Conditions

Conditions	Yield
With triethylamine In various solvent(s) at 83℃; for 24h;	92%

: 140-10-3
(E)-3-phenylacrylic acid

: 7285-83-8
2,4,6-tris(benzyloxy)-1,3,5-triazine

: 103-41-3
(E)-cinnamic acid benzyl ester

Conditions

Conditions	Yield
With trifluorormethanesulfonic acid In 1,4-dioxane at 20℃; for 5.5h; Molecular sieve;	91%

: 2495-35-4
benzylacrylate

: C17H12F5NO2

: 103-41-3
(E)-cinnamic acid benzyl ester

Conditions

Conditions	Yield
With tetrakis(acetonitrile)palladium bistriflate; (S)-4-methyl-2-(5-(trifluoromethyl)pyridin-2-yl)-4,5-dihydrooxazole; sodium carbonate; silver carbonate In 1,2-dichloro-ethane at 130℃; for 12h; Heck Reaction; Sealed tube; Inert atmosphere;	91%

: 140-10-3
(E)-3-phenylacrylic acid

: 2978-10-1, 113282-06-7
N,N'-diisopropyl-O-benzyl isourea

: 103-41-3
(E)-cinnamic acid benzyl ester

Conditions

Conditions	Yield
In tetrahydrofuran at 130℃; for 0.0833333h; Irradiation;	90%

: 13463-40-6, 71564-23-3
iron pentacarbonyl

: 536-74-3
phenylacetylene

: 100-51-6
benzyl alcohol

: 103-41-3
(E)-cinnamic acid benzyl ester

Conditions

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In N,N-dimethyl-formamide at 100℃; for 0.5h; regioselective reaction;	90%

...Expand

: 621-82-9
Cinnamic acid

: 100-51-6
benzyl alcohol

: 103-41-3
(E)-cinnamic acid benzyl ester

Conditions

Conditions	Yield
With 4-methyl-morpholine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride In tetrahydrofuran at 20℃; for 22h; Esterification;	89%
With triethylamine In dichloromethane 1.) 0 deg C; 2.) to room temperature and 1 h;	87%

: 18365-42-9
α-chloro-cinnamaldehyde

: 100-51-6
benzyl alcohol

: 103-41-3
(E)-cinnamic acid benzyl ester

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,3-bis(mesityl)imidazolium chloride In tetrahydrofuran at 20℃; Inert atmosphere; optical yield given as %de; stereoselective reaction;	88%

: 108-86-1
bromobenzene

: 2495-35-4
benzylacrylate

: 103-41-3
(E)-cinnamic acid benzyl ester

Conditions

Conditions	Yield
With C40H42N6O4Pd(2+)*2Br(1-); potassium carbonate In water at 80℃; for 5.5h; Heck Reaction;	86%
With potassium carbonate In ethanol; water at 80℃; for 2h; Catalytic behavior; Heck Reaction;

: 140-10-3
(E)-3-phenylacrylic acid

: 2-(benzyloxy)-4,6-dimethoxy-1,3,5-triazine

: 103-41-3
(E)-cinnamic acid benzyl ester

Conditions

Conditions	Yield
With trifluorormethanesulfonic acid In 1,4-dioxane at 20℃; for 0.0166667h; Molecular sieve; Inert atmosphere;	86%

: 102-92-1
Cinnamoyl chloride

: 100-51-6
benzyl alcohol

: 103-41-3
(E)-cinnamic acid benzyl ester

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 17h; Inert atmosphere;	84%

: 103-41-3
(E)-cinnamic acid benzyl ester

: 22767-96-0
Benzyl 3-phenylpropionate

Conditions

Conditions	Yield
With hydrogen In toluene at 25℃; for 1h; Catalytic behavior;	99%
With hydrogen; palladium In tetrahydrofuran for 24h;	98%
With hydrogen; TMSB; palladium In ethanol at 20℃; under 760 Torr; for 24h;	98%

: 103-41-3
(E)-cinnamic acid benzyl ester

: 501-52-0
3-Phenylpropionic acid

Conditions

Conditions	Yield
With formic acid; potassium hydroxide In ethanol at 70℃; for 1h;	97%
With ammonium formate; silica gel; palladium dichloride In formic acid; water for 0.133333h; microwave irradiation;	84%

: 103-41-3
(E)-cinnamic acid benzyl ester

: 140-10-3
(E)-3-phenylacrylic acid

Conditions

Conditions	Yield
With phosphate buffer; Bacillus sublilis esterase In methanol; hexane at 37℃; for 24h; Product distribution; Further Variations:; Reagents;	95%

: 103-41-3
(E)-cinnamic acid benzyl ester

: 98-80-6
phenylboronic acid

: (S,R)-4-(benzyloxycarbonyl)-2,5-diphenyl-1,3,2-dioxaborolane

Conditions

Conditions	Yield
With K2; 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium hexacyanoferrate(III); potassium carbonate In tert-butyl alcohol at 20℃; for 12h;	95%

: 103-41-3
(E)-cinnamic acid benzyl ester

: 212555-23-2
(2,4,6-trimethoxyphenyl)methanethiol

: C26H28O5S

Conditions

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 4h; Michael addition;	91%

: 530-48-3
1,1-Diphenylethylene

: 103-41-3
(E)-cinnamic acid benzyl ester

: DL-benzyl (1R,2R)-2,3,3-triphenylcyclobutane-1-carboxylate

Conditions

Conditions	Yield
With fac-tris(2-phenylpyridinato-N,C2')iridium(III) In dichloromethane at 20℃; for 5h; Inert atmosphere; Sealed tube; Irradiation; diastereoselective reaction;	91%

: 530-48-3
1,1-Diphenylethylene

: 103-41-3
(E)-cinnamic acid benzyl ester

: benzyl 2,3,3-triphenylcyclobutyl-1-carboxylate

Conditions

Conditions	Yield
With tris[2-phenylpyridinato-C2,N]iridium(III) In 1,2-dichloro-ethane at 25℃; for 5h; Inert atmosphere; Irradiation;	91%

Benzyl cinnamate Consensus Reports

Reported in EPA TSCA Inventory.

Benzyl cinnamate 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.

Product Name

Benzyl cinnamate

Synthetic route

Benzyl cinnamate Consensus Reports

Benzyl cinnamate Specification

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