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Cas Database |
| Name |
Methyl cinnamate |
EINECS | 203-093-8 |
| CAS No. | 103-26-4 | Density | 1.078 g/cm3 |
| PSA | 26.30000 | LogP | 1.87280 |
| Solubility | insoluble in water | Melting Point |
33.5-36 °C |
| Formula | C10H10O2 | Boiling Point | 261.9 °C at 760 mmHg |
| Molecular Weight | 162.188 | Flash Point | 141.3 °C |
| Transport Information | N/A | Appearance | White to light yellow crystal or liquid |
| Safety | 22-24/25 | Risk Codes | N/A |
| Molecular Structure |
|
Hazard Symbols | N/A |
| Synonyms |
Methyl 3-phenyl-2-propenoate;2-propenoic acid, 3-phenyl-, methyl ester, (2E)-;methyl 3-phenylprop-2-enoate;2-Propenoic acid, 3-phenyl-, methyl ester;Methyl 3-phenylpropenoate;Methyl cinnamate (natural);Methyl 3-phenylacrylate;Methyl cinnamylate;methyl (2E)-3-phenylacrylate;Cinnamic acid methyl ester;Methyl Cinnamate 98%min;Methyl cinnamate nat.;Methyl Cinnamate Natural; |
Article Data | 1104 |
Methyl cinnamate Synthetic route
| Conditions | Yield |
|---|---|
| With sulfuric acid at 65℃; for 16h; | 100% |
| With sulfuric acid | 100% |
| With ammonium cerium(IV) nitrate at 20℃; for 240h; | 99% |
| Conditions | Yield |
|---|---|
| ς4,λ5-phosphinine palladium In 1-methyl-pyrrolidin-2-one at 100℃; for 120h; Heck reaction; | 100% |
| With palladium diacetate; 15-crown-15 tagged triarylphoshine; triethylamine In tetrahydrofuran for 8h; Heck reaction; Heating; | 100% |
| With triethylamine; polymer(fiber)-supported palladium In 1,4-dioxane at 100℃; for 1h; Heck reaction; | 100% |
- 103-26-4
Methyl cinnamate
| Conditions | Yield |
|---|---|
| With boron trifluoride diethyl etherate In dichloromethane for 1h; | 100% |
- 369-57-3
benzenediazonium tetrafluoroborate
- 292638-85-8
acrylic acid methyl ester
- 103-26-4
Methyl cinnamate
| Conditions | Yield |
|---|---|
| With palladium(II) acetate In water at 20℃; for 0.5h; Green chemistry; stereoselective reaction; | 100% |
| With 1-(2-hydroxyethyl)-3-methylimidazolium prolinate; palladium diacetate In neat (no solvent) at 20℃; for 0.5h; Heck Reaction; Green chemistry; | 99% |
| With Pd/Al2O3 In methanol at 25℃; | 96% |
| Conditions | Yield |
|---|---|
| With bis-triphenylphosphine-palladium(II) chloride; toluene-4-sulfonic acid; 1,4-di(diphenylphosphino)-butane In acetonitrile at 110℃; under 5171.62 Torr; for 1h; Autoclave; regioselective reaction; | 100% |
| With triiron dodecarbonyl; triethylamine In tetrahydrofuran at 90℃; under 1034.32 Torr; for 0.333333h; Inert atmosphere; Microwave irradiation; regioselective reaction; | 57% |
| With 1,1'-binaphthyl-2,2'-diyl hydrogenphosphate; 1,2-bis[di(t-butyl)phosphinomethyl]benzene; bis(dibenzylideneacetone)-palladium(0) In dichloromethane at 20℃; for 14h; regioselective reaction; | 11% |
| Conditions | Yield |
|---|---|
| Stage #1: methanol With 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,4-dimethyl-1,2,4-triazolium iodide 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; | 99% |
| With 2,3-dicyano-5,6-dichloro-p-benzoquinone; Amberlyst 15 at 20℃; for 20h; Product distribution / selectivity; | 98% |
| With 2,3-dicyano-5,6-dichloro-p-benzoquinone; acetic acid In toluene for 6h; Product distribution / selectivity; Heating / reflux; | 98% |
| Conditions | Yield |
|---|---|
| With palladium diacetate; acetic anhydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone In acetic acid at 90℃; for 27h; Heck reaction; | 99% |
| With potassium fluoride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; bis(acetylacetonato)palladium(II); propionic acid at 20℃; for 2h; Oxidative Heck reaction; Inert atmosphere; diastereoselective reaction; | 96% |
| SiO2-Rh(0) In water; toluene at 100℃; for 10h; Heck-type reaction; | 90% |
| Conditions | Yield |
|---|---|
| With 4-methyl-morpholine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride at 20℃; for 2h; Esterification; | 99% |
| Conditions | Yield |
|---|---|
| With [t-Bu2SnCl(OH)]2 In toluene for 24h; Heating; | 99% |
| With [2,2]bipyridinyl; bis(1,5-cyclooctadiene)nickel (0) In toluene at 25℃; for 12h; Sealed tube; Inert atmosphere; Green chemistry; chemoselective reaction; | 85% |
- 21204-67-1
methyl (triphenylphosphoranylidene)acetate
- 100-51-6
benzyl alcohol
A
- 19713-73-6
methyl (2Z)-3-phenylprop-2-enoate
B
- 103-26-4
Methyl cinnamate
| Conditions | Yield |
|---|---|
| Stage #1: benzyl alcohol With Celite; pyridinium chlorochromate In dichloromethane at 20℃; for 3h; Stage #2: methyl (triphenylphosphoranylidene)acetate In dichloromethane at 20℃; for 24h; Wittig olefination; | A n/a B 99% |
| With oxygen In N,N-dimethyl-formamide at 80℃; for 18h; Reagent/catalyst; Solvent; Temperature; Time; Wittig Olefination; Overall yield = 49 %; | A n/a B n/a |
Methyl cinnamate Consensus Reports
Reported in EPA TSCA Inventory.
Methyl cinnamate Specification
Methyl cinnamate, with CAS number of 103-36-6, can be called 2-Propenoicacid,3-phenyl-,methylester; 3-phenyl-2-propenoicacimethylester; 3-phenyl-prop-2-enoicacidmethylester; Methyl 3-phenyl-2-propenoate; Methyl ester of Cinnamic acid; methyl3-phenyl-2-propenoate; Trans-3-phenylacrylic acid methyl ester. It is a white to light yellow fused crystalline mas, Moderately toxic by ingestion. When heated to decomposition it emits acrid smoke and irritating fumes. Methyl cinnamate is the methyl ester of cinnamic acid. It is found naturally in a variety of plants, including in fruits, like strawberry and some culinary spices, such as Sichuan pepper and some varieties of basil.
Physical properties about Methyl cinnamate are: (1)ACD/LogP: 2.458; (2)ACD/LogD (pH 5.5): 2.46; (3)ACD/LogD (pH 7.4): 2.46; (4)ACD/BCF (pH 5.5): 43.44 ; (5)ACD/BCF (pH 7.4): 43.44; (6)ACD/KOC (pH 5.5): 517.61; (7)ACD/KOC (pH 7.4): 517.61; (8)#H bond acceptors: 2; (9)#Freely Rotating Bonds: 3; (10)Index of Refraction: 1.558 ; (11)Molar Refractivity: 48.55 cm3; (12)Molar Volume: 150.398 cm3; (13)Polarizability: 19.247 10-24cm3; (14)Surface Tension: 38.5470008850098 dyne/cm; (15)Density: 1.078 g/cm3; (16)Flash Point: 141.265 °C; (17)Enthalpy of Vaporization: 49.966 kJ/mol; (18)Boiling Point: 261.899 °C at 760 mmHg; (19)Vapour Pressure: 0.0109999999403954 mmHg at 25°C;
You can still convert the following datas into molecular structure:
(1)InChI=1S/C10H10O2/c1-12-10(11)8-7-9-5-3-2-4-6-9/h2-8H,1H3/b8-7+;
(2)InChIKey=CCRCUPLGCSFEDV-BQYQJAHWSA-N;
(3)Smilesc1(/C=C/C(=O)OC)ccccc1;
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