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% |
Methyl cinnamate
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In dichloromethane for 1h; | 100% |
benzenediazonium tetrafluoroborate
acrylic acid methyl ester
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% |
methanol
3-((E)-3-phenyl-2-propenoyl)-1,3-oxazolidin-2-one
Methyl cinnamate
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% |
methyl (triphenylphosphoranylidene)acetate
benzyl alcohol
A
methyl (2Z)-3-phenylprop-2-enoate
B
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 |
Conditions | Yield |
---|---|
With 1-(2-hydroxyethyl)-3-methylimidazolium prolinate; palladium diacetate In neat (no solvent) at 20℃; for 0.5h; silica; Heck Reaction; Green chemistry; | 99% |
Conditions | Yield |
---|---|
With trimethylphosphane In dichloromethane; toluene at 20℃; for 1.5h; Solvent; | 99% |
Conditions | Yield |
---|---|
With trimethylphosphane In toluene at 20℃; for 3h; Reagent/catalyst; Solvent; | A 99% B 88% |
methyl β-phenyl-β-methoxy-propionate
Methyl cinnamate
Conditions | Yield |
---|---|
With sodium chloride; sulfuric acid; sodium methylate; sodium hydrogencarbonate; benzaldehyde In acetic acid methyl ester; water; ethyl acetate; toluene | 98.1% |
With hydrogenchloride; sodium chloride; sulfuric acid; sodium methylate; benzaldehyde In methanol; acetic acid methyl ester; toluene | |
With trifluorormethanesulfonic acid In toluene at 75℃; for 40h; Inert atmosphere; | n/a |
methyl (2Z)-3-phenylprop-2-enoate
Methyl cinnamate
Conditions | Yield |
---|---|
With tri-n-butyl-tin hydride; triethylamine; palladium diacetate In dichloromethane for 8h; Heating; | 98% |
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 2h; Heating; | 96% |
diphenyldisulfane In tetrahydrofuran for 7h; Heating; | 93% |
rac-(R,S)-methyl 2,3-dibromo-3-phenylpropanoate
Methyl cinnamate
Conditions | Yield |
---|---|
With zinc In acetic acid for 0.0166667h; microwave irradiation; | 98% |
With dimethyl sulfoxide at 75℃; for 2h; | 97% |
With 1-methyl-3-pentyl-1H-imidazolium tetrafluoroborate at 130 - 135℃; for 0.0333333h; microwave irradiation; | 95% |
Conditions | Yield |
---|---|
With sodium hydroxide; dihydrogen peroxide | 98% |
With Merrifield resin-supported N3=P(MeNCH2CH2)3N at 23 - 25℃; for 3h; Inert atmosphere; | 94% |
acrylonitrile; triphenylphosphine at 25℃; for 24h; | 60 % Chromat. |
Conditions | Yield |
---|---|
With polystyrene-supported palladacycle catalyst; sodium acetate In N,N-dimethyl acetamide at 130℃; for 48h; Heck reaction; | 98% |
With sodium acetate; polystyrene-supported palladacycle In N,N-dimethyl acetamide at 130℃; for 48h; Heck reaction; | 97% |
With triethylamine In N,N-dimethyl-formamide at 120℃; for 6h; Heck Reaction; | 95% |
Methyl erythro-2,3-dibromo-3-phenylpropanoate
Methyl cinnamate
Conditions | Yield |
---|---|
With sodium sulfide; cetyltributylphosphonium bromide In toluene at 25℃; for 0.0833333h; | 97% |
With N,N-dimethyl-formamide at 155 - 160℃; for 1h; | 93% |
With indium(III) chloride; sodium tetrahydroborate In acetonitrile at -10℃; for 3.25h; | 80% |
methanol
carbon monoxide
phenylacetylene
A
2-phenyl-acrylic acid methyl ester
B
Methyl cinnamate
Conditions | Yield |
---|---|
With palladium diacetate; toluene-4-sulfonic acid; 2-(diphenylphosphino)pyridine at 60℃; under 41253.3 - 45003.6 Torr; | A 97% B n/a |
With bis-triphenylphosphine-palladium(II) chloride; toluene-4-sulfonic acid; 1,4-di(diphenylphosphino)-butane In tetrahydrofuran at 110℃; under 5171.62 Torr; for 1h; Autoclave; regioselective reaction; | A 90% B 10% |
With palladium diacetate; toluene-4-sulfonic acid; 1,4-di(diphenylphosphino)-butane In acetonitrile at 110℃; under 5171.62 Torr; for 1h; Autoclave; regioselective reaction; | A 11% B 89% |
Conditions | Yield |
---|---|
With chromium dichloride In tetrahydrofuran at 20℃; for 12h; | 97% |
With manganese In tetrahydrofuran for 3h; Heating; | 72% |
With manganese In tetrahydrofuran for 3h; Reflux; Inert atmosphere; optical yield given as %de; stereoselective reaction; | 72% |
With chloro-trimethyl-silane; zinc In tetrahydrofuran at 50℃; for 3h; | 70% |
Conditions | Yield |
---|---|
With perchloric acid; sodium percarbonate; vanadia for 0.3h; Heating; | 97% |
With Bromotrichloromethane; C14H18N3(1+)*ClO4(1-); rhodamine 6G; potassium carbonate In tetrahydrofuran at 20℃; for 3h; Inert atmosphere; Irradiation; | 79% |
With perchloric acid; dihydrogen peroxide; vanadia In water for 2h; oxidative esterification; Heating; | 95 % Chromat. |
methanol
{3-(3-phenylprop-2-enoyloxy)propyl}trimethylammonium bistrifluoromethanesulfonimidate
Methyl cinnamate
Conditions | Yield |
---|---|
With hydrogenchloride In water for 3h; Heck reaction; Inert atmosphere; Reflux; | 97% |
Conditions | Yield |
---|---|
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 0.75h; Esterification; | 96% |
With potassium hydroxide In dimethyl sulfoxide at 20℃; for 2h; | 81% |
In N,N-dimethyl-formamide Inert atmosphere; |
Methyl cinnamate
Conditions | Yield |
---|---|
With pyridine N-oxide In dichloromethane at 23℃; for 0.333333h; | 96% |
methanol
iron pentacarbonyl
phenylacetylene
Methyl cinnamate
Conditions | Yield |
---|---|
With 1,4-diaza-bicyclo[2.2.2]octane In N,N-dimethyl-formamide at 100℃; for 0.5h; regioselective reaction; | 96% |
Conditions | Yield |
---|---|
With potassium bromide In N,N-dimethyl-formamide at 130℃; for 12h; Schlenk technique; | 96% |
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; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Heck Reaction; Sealed tube; Inert atmosphere; | 96% |
methyl (2R*,3S*)-2-(tert-butyldimethylsilyl)-3-hydroxy-3-phenylpropionate
Methyl cinnamate
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran Ambient temperature; | 95% |
3-phenyl-2-selena<2.2.1>bicyclohept-5-ene
methyl (triphenylphosphoranylidene)acetate
Methyl cinnamate
Conditions | Yield |
---|---|
In toluene for 38h; Heating; | 95% |
Conditions | Yield |
---|---|
With hydrogen; palladium In ethyl acetate at 25℃; under 760.051 Torr; for 1h; | 100% |
With hydrogen; polymer incarcerated platinum In tetrahydrofuran at 20℃; for 1h; atmospheric pressure; | 100% |
With hydrogen; palladium in polystyrene In tetrahydrofuran at 25℃; under 760.051 Torr; for 1h; | 100% |
Methyl cinnamate
methyl (2S,3R)-3-phenyl-2,3-dihydroxypropanoate
Conditions | Yield |
---|---|
With osmium(VIII) oxide; potassium carbonate; potassium hexacyanoferrate(III); methanesulfonamide; chiral triazine catalyst In water; tert-butyl alcohol at 0℃; for 14h; | 100% |
With (3a,9R,3'''a,4'"b,9'"R)-9,9'-[1,4-phthalazinediylbis(oxy)]bis[6'-(methyloxy)-10,11-dihydrocinchonan]; 4-methylmorpholine N-oxide; Mg(1-x)Al(x)(OH)2(Cl)2*zH2O-OsO4 In water; tert-butyl alcohol at 20℃; for 12h; | 96% |
With (3a,9R,3'''a,4'"b,9'"R)-9,9'-[1,4-phthalazinediylbis(oxy)]bis[6'-(methyloxy)-10,11-dihydrocinchonan]; tetraethylammonium acetate; dihydrogen peroxide; polyaniline-supported Os-Re In tert-butyl alcohol at 0℃; Sharpless asymmetric dihydroxylation; | 94% |
Methyl cinnamate
methyl (2R,3S)-2,3-dihydroxy-3-phenylpropanoate
Conditions | Yield |
---|---|
With 1,4-bis(9-O-dihydroquinidine)phthalazine In water; tert-butyl alcohol at 20℃; for 10h; | 100% |
With AD-mix-α | 99% |
With osmium(VIII) oxide; dihydroquinidine 9-O-(4-chlorobenzoate); potassium hexacyanoferrate(III) | 92% |
Conditions | Yield |
---|---|
Stage #1: 1-octadecanol; Methyl cinnamate In xylene for 0.5h; Heating; Stage #2: With TiO(acac)2 In xylene for 14h; Heating; | 100% |
methanol
Methyl cinnamate
methyl (±)-anti-2-iodo-3-methoxy-3-phenylpropanoate
Conditions | Yield |
---|---|
With ammonium cerium (IV) nitrate; iodine at 50℃; for 15h; | 99% |
With iodine; silver nitrate for 6h; Ambient temperature; | 78% |
With iodine; silver nitrate | |
Yield given. Multistep reaction; |
Methyl cinnamate
N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine
(3SR,4SR)methyl 1-benzyl-4-phenylpyrrolidine-3-carboxylate
Conditions | Yield |
---|---|
With trifluoroacetic acid In dichloromethane at 0℃; | 99% |
trifluoroacetic acid In dichloromethane for 3h; Ambient temperature; | 87% |
With trifluoroacetic acid In dichloromethane |
Methyl cinnamate
methyl (2Z)-3-phenylprop-2-enoate
Conditions | Yield |
---|---|
With 1,3,6,8-tetraphenylpyrimido<5,4-g>pteridine-2,4,5,7(1H,3H,6H,8H)-tetrone 10-oxide In acetonitrile at 30℃; for 24h; Reagent/catalyst; Concentration; Wavelength; Inert atmosphere; UV-irradiation; | 99% |
boron trifluoride diethyl etherate In dichloromethane for 3h; Irradiation; | 85% |
In cyclohexane Irradiation; | 64% |
Conditions | Yield |
---|---|
With C17H16BrMnNO3P; potassium tert-butylate; hydrogen In 1,4-dioxane at 100℃; under 37503.8 Torr; for 6h; Autoclave; chemoselective reaction; | 99% |
With sodium tetrahydroborate; [fac-8-(2-diphenylphosphinoethyl)amidotrihydroquinoline]RuH(PPh)3(CO); hydrogen In tetrahydrofuran at 120℃; under 37503.8 Torr; for 18h; Inert atmosphere; Autoclave; | 87% |
With lithium aluminium tetrahydride In tetrahydrofuran for 0.166667h; Ambient temperature; | 100 % Chromat. |
With sodium tetrahydroborate; [fac-8-(2-diphenylphosphinoethyl)amidotrihydroquinoline]RuH(PPh3)(CO); hydrogen In tetrahydrofuran at 120℃; under 38002.6 Torr; for 18h; Autoclave; Industrial scale; |
Methyl cinnamate
rac-(R,S)-methyl 2,3-dibromo-3-phenylpropanoate
Conditions | Yield |
---|---|
With hydrogen bromide; dihydrogen peroxide In tetrachloromethane at 20℃; for 2h; Bromination; | 99% |
With Oxone; ammonium bromide In water; acetonitrile for 12h; Reflux; stereoselective reaction; | 97% |
With Selectfluor; potassium bromide In water; acetonitrile for 2h; | 89% |
Conditions | Yield |
---|---|
With sodium 4-tert-butylphenolate; sodium t-butanolate In tetrahydrofuran under 40 - 50 Torr; for 6h; | 99% |
With potassium tert-butylate In tetrahydrofuran Ambient temperature; | 96% |
4-methylphenylboronic acid
Methyl cinnamate
methyl 3-(4-methylphenyl)-3-phenylpropionate
Conditions | Yield |
---|---|
chloro(1,5-cyclooctadiene)rhodium(I) dimer In water at 90℃; for 6h; | 99% |
With potassium hydroxide; [Rh(OH)(cod)]2 In 1,2-dimethoxyethane at 0℃; for 6h; | 97% |
With chlorobis(ethylene)rhodium(I) dimer; C47H55O7P; potassium hydroxide In 1,4-dioxane; water at 20℃; for 24h; Inert atmosphere; | 73% |
Conditions | Yield |
---|---|
With [bis(acetoxy)iodo]benzene; potassium carbonate In dichloromethane at 20℃; for 12h; | 99% |
[bis(acetoxy)iodo]benzene
acetic anhydride
Methyl cinnamate
acetic acid
Conditions | Yield |
---|---|
Stage #1: [bis(acetoxy)iodo]benzene; Methyl cinnamate; acetic acid With boron trifluoride diethyl etherate In water at 20℃; for 8h; Stage #2: acetic anhydride In water at 20℃; optical yield given as %de; diastereoselective reaction; | 99% |
2-(furan-3-yl)acetic acid
Methyl cinnamate
Conditions | Yield |
---|---|
Stage #1: 2-(furan-3-yl)acetic acid With n-butyllithium; N1,N3-bis((R)-1-phenyl-2-(piperidin-1-yl)ethyl)propane-1,3-diamine In tetrahydrofuran; hexane at -90 - 0℃; for 0.583333h; Michael Addition; Inert atmosphere; Stage #2: Methyl cinnamate In tetrahydrofuran; hexane at -90℃; for 0.5h; Michael Addition; Inert atmosphere; enantioselective reaction; | 99% |
(p-hydroxyphenyl)boronic acid
Methyl cinnamate
Conditions | Yield |
---|---|
With C50H56Cl2O4Rh2 In ethanol at 60℃; for 12h; Schlenk technique; Inert atmosphere; Green chemistry; enantioselective reaction; | 99% |
Reported in EPA TSCA Inventory.
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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