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CAS No.: | 103-41-3 |
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Name: | Benzyl cinnamate |
Article Data: | 164 |
Molecular Structure: | |
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 |
Conditions | Yield |
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With titanium tetrachloride; triethylamine In dichloromethane at 0 - 25℃; Inert atmosphere; stereoselective reaction; | 99% |
With iodine; magnesium; mercury dichloride Reagens 4: Xylol; |
Conditions | Yield |
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With triethylamine In dichloromethane at 20℃; | 99% |
C21H16N2O2
sodium phenyl-methanolate
(E)-cinnamic acid benzyl ester
Conditions | Yield |
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In tetrahydrofuran Ambient temperature; | 98% |
Conditions | Yield |
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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 |
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With boron trifluoride diethyl etherate In 1,2-dimethoxyethane at 20℃; for 2h; Inert atmosphere; | 98% |
Conditions | Yield |
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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 |
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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% |
Conditions | Yield |
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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 |
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In acetonitrile at 125℃; for 0.05h; microwave irradiation; | 96% |
Conditions | Yield |
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dmap In N,N-dimethyl-formamide at 20℃; for 5h; | 96% |
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. |