Conditions | Yield |
---|---|
With titanium tetrachloride; triethylamine In dichloromethane at 0 - 25℃; Inert atmosphere; stereoselective reaction; | 99% |
With iodine; magnesium; mercury dichloride Reagens 4: Xylol; |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; | 99% |
C21H16N2O2
sodium phenyl-methanolate
(E)-cinnamic acid benzyl ester
Conditions | Yield |
---|---|
In tetrahydrofuran Ambient temperature; | 98% |
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; |
(E)-benzyl-3-(2-((E)-piperidin-1-yldiazenyl)phenyl)acrylate
(E)-cinnamic acid benzyl ester
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In 1,2-dimethoxyethane at 20℃; for 2h; Inert atmosphere; | 98% |
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% |
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% |
malonic acid monobenzyl ester
benzaldehyde
(E)-cinnamic acid benzyl ester
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% |
Conditions | Yield |
---|---|
In acetonitrile at 125℃; for 0.05h; microwave irradiation; | 96% |
Conditions | Yield |
---|---|
dmap In N,N-dimethyl-formamide at 20℃; for 5h; | 96% |
Conditions | Yield |
---|---|
With trimethylphosphane In dichloromethane; toluene at 20℃; for 3h; | 96% |
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% |
Conditions | Yield |
---|---|
With 1,3-dimethylimidazolinium methanesulfonate at 90℃; for 0.5h; | 95% |
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. |
(E)-3-phenylacrylic acid
2-(phenylmethoxy)benzaldehyde
(E)-cinnamic acid benzyl ester
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% |
3-((E)-3-phenyl-2-propenoyl)-1,3-oxazolidin-2-one
benzyl alcohol
(E)-cinnamic acid benzyl ester
Conditions | Yield |
---|---|
With [t-Bu2SnCl(OH)]2 In toluene for 14h; Heating; | 94% |
(E)-3-phenylacrylic acid
2'-benzyloxyacetophenone
(E)-cinnamic acid benzyl ester
Conditions | Yield |
---|---|
With 1-methyl-pyrrolidin-2-one; trifluorormethanesulfonic acid In chlorobenzene at 130℃; for 24h; Inert atmosphere; Schlenk technique; | 94% |
(E)-3-phenylacrylic acid
1,2-di(benzyloxy)benzene
(E)-cinnamic acid benzyl ester
Conditions | Yield |
---|---|
With 1-methyl-pyrrolidin-2-one; trifluorormethanesulfonic acid In chlorobenzene at 130℃; for 24h; Inert atmosphere; Schlenk technique; | 93% |
C21H16N2O2
benzyl alcohol
(E)-cinnamic acid benzyl ester
Conditions | Yield |
---|---|
zinc(II) chloride In dichloromethane; acetonitrile for 18h; Ambient temperature; | 92% |
Conditions | Yield |
---|---|
With sodium 4-tert-butylphenolate; sodium t-butanolate In tetrahydrofuran | 92% |
Conditions | Yield |
---|---|
With triethylamine In various solvent(s) at 83℃; for 24h; | 92% |
(E)-3-phenylacrylic acid
2,4,6-tris(benzyloxy)-1,3,5-triazine
(E)-cinnamic acid benzyl ester
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid In 1,4-dioxane at 20℃; for 5.5h; Molecular sieve; | 91% |
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% |
(E)-3-phenylacrylic acid
N,N'-diisopropyl-O-benzyl isourea
(E)-cinnamic acid benzyl ester
Conditions | Yield |
---|---|
In tetrahydrofuran at 130℃; for 0.0833333h; Irradiation; | 90% |
iron pentacarbonyl
phenylacetylene
benzyl alcohol
(E)-cinnamic acid benzyl ester
Conditions | Yield |
---|---|
With 1,4-diaza-bicyclo[2.2.2]octane In N,N-dimethyl-formamide at 100℃; for 0.5h; regioselective reaction; | 90% |
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% |
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% |
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; |
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid In 1,4-dioxane at 20℃; for 0.0166667h; Molecular sieve; Inert atmosphere; | 86% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; for 17h; Inert atmosphere; | 84% |
(E)-cinnamic acid benzyl ester
Benzyl 3-phenylpropionate
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% |
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% |
Conditions | Yield |
---|---|
With phosphate buffer; Bacillus sublilis esterase In methanol; hexane at 37℃; for 24h; Product distribution; Further Variations:; Reagents; | 95% |
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% |
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 4h; Michael addition; | 91% |
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% |
Conditions | Yield |
---|---|
With tris[2-phenylpyridinato-C2,N]iridium(III) In 1,2-dichloro-ethane at 25℃; for 5h; Inert atmosphere; Irradiation; | 91% |
Reported in EPA TSCA Inventory.
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. |
About|Contact|Cas|Product Name|Molecular|Country|Encyclopedia
Message|New Cas|MSDS|Service|Advertisement|CAS DataBase|Article Data|Manufacturers | Chemical Catalog
©2008 LookChem.com,License: ICP
NO.:Zhejiang16009103
complaints:service@lookchem.com Desktop View