(E)-3-phenylpropenal
(E)-3-phenylacrylic acid
Conditions | Yield |
---|---|
With cobalt(II) 2,9,16,23-phthalocyanine tetrasulfonic acid In water; acetonitrile at 20℃; under 760.051 Torr; for 150h; UV-irradiation; | 100% |
With oxygen; potassium carbonate; 1,3-bis(mesityl)imidazolium chloride In water; N,N-dimethyl-formamide at 25℃; for 16h; | 99% |
With sodium chlorite; sodium dihydrogenphosphate; dihydrogen peroxide In toluene at 10℃; for 1h; Product distribution; var. solvents; other reaction partners; other aldehydes; | 95% |
Conditions | Yield |
---|---|
With barium dihydroxide In methanol at 80℃; for 2h; | 100% |
98.5% | |
98.5% |
Conditions | Yield |
---|---|
With triethylamine; PdCl2(4,4'-bis(n-C10F21CH2OCH2)-2,2'-bpy) In N,N-dimethyl-formamide at 140℃; for 3h; Heck reaction; | 100% |
With potassium carbonate; palladium dichloride In water at 20 - 100℃; Heck reaction; Inert atmosphere; | 99% |
With potassium hydroxide In water at 90℃; for 5h; Mizoroki-Heck reaction; | 99% |
(E)-vinyl cinnamate
(E)-3-phenylacrylic acid
Conditions | Yield |
---|---|
With water; dichloro bis(acetonitrile) palladium(II) at 40℃; for 1h; | 100% |
Conditions | Yield |
---|---|
With piperidine; pyridine at 22℃; for 3h; ultrasound; | 99% |
With piperidine; pyridine at 90℃; for 1h; | 99% |
With ammonium acetate for 0.05h; Irradiation; | 98% |
Conditions | Yield |
---|---|
With copper acetylacetonate; oxygen; sodium hydroxide; 1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene In water at 50℃; under 760.051 Torr; for 12h; Sealed tube; | 99% |
With pyridine; air; copper es entsteht Kupfer(II)-cinnamat; | |
With air |
(E)-allyl cinnamate
(E)-3-phenylacrylic acid
Conditions | Yield |
---|---|
[(cyclopentadienyl)bis(acetonitrile)(triphenylphosphine)ruthenium(II)] hexafluorophosphate In methanol at 25℃; for 6h; | 99% |
With palladium 10% on activated carbon; silica gel In methanol at 120℃; for 0.5h; Flow reactor; | 95% |
With iodine; dimethyl sulfoxide for 0.333333h; Heating; | 87% |
With phosphate buffer; Bacillus subtilis esterase BS2 In methanol; hexane at 37℃; for 3h; pH=7.4; Product distribution; Further Variations:; Reagents; reaction times; enzyme/substrate ratios; | 83% |
With pyrrolidine; tetrakis(triphenylphosphine) palladium(0); triphenylphosphine In acetonitrile at 0℃; Yield given; |
Conditions | Yield |
---|---|
With ruthenium trichloride; potassium hydroxide; potassium peroxomonosulphate for 3h; Ambient temperature; | 99% |
With potassium permanganate; Rexyn 101 H ion exchange resin In dichloromethane for 4.15h; Heating; | 95% |
With [bis(acetoxy)iodo]benzene; iodine In acetonitrile at 20℃; for 3h; | 93% |
Conditions | Yield |
---|---|
[1,3-bis-(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro(O-isopropoxyphenylmethylene)ruthenium In dichloromethane at 100℃; for 0.5h; microwave irradiation; | 99% |
A
tetraphenylantimony(V) chloride
B
(E)-3-phenylacrylic acid
Conditions | Yield |
---|---|
With aq. HCl | A 99% B n/a |
erythro-2,3-dibromo-3-phenylpropanoic acid
(E)-3-phenylacrylic acid
Conditions | Yield |
---|---|
With sodium selenite; rac-cysteine In tetrahydrofuran; water at 0℃; for 0.5h; | 98% |
With samarium In tetrahydrofuran for 0.166667h; Ambient temperature; | 93% |
With bismuth(III) chloride; indium In methanol at 20℃; for 1h; Sonication; chemoselective reaction; | 89% |
Conditions | Yield |
---|---|
Stage #1: benzaldehyde; acetic acid With titanium tetrachloride In dichloromethane at 25℃; for 0.333333h; Inert atmosphere; Stage #2: With triethylamine In dichloromethane at 25℃; Inert atmosphere; stereoselective reaction; | 98% |
With pyridine; dmap; lithium chloride In 1-methyl-pyrrolidin-2-one at 185 - 190℃; for 11h; | 78% |
With pyridine; dmap; sodium tetraborate decahydrate; N-benzyl-N,N,N-triethylammonium chloride In 1-methyl-pyrrolidin-2-one at 185 - 190℃; for 9h; | 77% |
(E)-3-Phenyl-acrylic acid (E)-4-trimethylsilanyl-but-2-enyl ester
(E)-3-phenylacrylic acid
Conditions | Yield |
---|---|
With methanol; tetrakis(triphenylphosphine) palladium(0) In dichloromethane for 2h; Ambient temperature; | 98% |
Conditions | Yield |
---|---|
With water; potassium hydroxide In ethanol at 80℃; for 24h; Catalytic behavior; Temperature; Heck Reaction; Schlenk technique; Inert atmosphere; Green chemistry; | 98% |
With potassium hydroxide In water; N,N-dimethyl-formamide at 80℃; for 6h; Catalytic behavior; Heck Reaction; | 91% |
With triethylamine; di-(3-methylphenyl)phosphinopolystyrene palladium catalyst In acetonitrile at 80℃; for 20h; Product distribution; Further Variations:; Catalysts; Heck coupling reaction; | 100 % Spectr. |
Conditions | Yield |
---|---|
Stage #1: acetic acid tert-butyl ester; benzaldehyde With titanium tetrachloride In dichloromethane for 0.5h; Stage #2: With triethylamine | 98% |
Conditions | Yield |
---|---|
With sodium hydroxide In water | 97% |
With bis(tri-n-butyltin)oxide In benzene at 80℃; for 24h; | 90% |
With bis(tri-n-butyltin)oxide In benzene at 80℃; for 24h; | 90% |
(trimethylsilyl)ketene bis(trimethylsilyl) acetal
benzaldehyde
(E)-3-phenylacrylic acid
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In tetrahydrofuran for 4h; Ambient temperature; | 97% |
With cesium fluoride In N,N-dimethyl-formamide for 0.5h; | 96% |
Stage #1: (trimethylsilyl)ketene bis(trimethylsilyl) acetal; benzaldehyde With potassium hydroxide In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: With ammonium chloride In water | 96% |
(E)-1-(1H-indol-1-yl)-3-phenylprop-2-en-1-one
(E)-3-phenylacrylic acid
Conditions | Yield |
---|---|
With lithium hydroxide; dihydrogen peroxide In tetrahydrofuran; water for 3.4h; Product distribution; other reag.; other solvent; | 97% |
Conditions | Yield |
---|---|
With nitric acid In dichloromethane at 0℃; for 2h; | A 60% B 96% |
tert-butyl cinnamate
(E)-3-phenylacrylic acid
Conditions | Yield |
---|---|
With sulfuric acid In dichloromethane at 20℃; for 6h; | 96% |
With KSF clay In acetonitrile for 3h; Heating; | 95% |
Conditions | Yield |
---|---|
With tetrabutylammomium bromide; sodium carbonate; triethylamine In water; N,N-dimethyl-formamide at 110℃; for 4h; Heck Reaction; Green chemistry; | 96% |
With potassium carbonate In water for 12h; Heck Reaction; Inert atmosphere; Reflux; | 93% |
Stage #1: acrylic acid With lithium tert-butoxide In water at 20℃; for 0.166667h; Inert atmosphere; Green chemistry; Stage #2: bromobenzene With bis-(1-methylimidazole)palladium(II) dichloride In water at 100℃; for 12h; Reagent/catalyst; Heck Reaction; Green chemistry; | 92% |
(E)-3-phenylacrylic acid
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 0.5h; | 96% |
(E)-3-phenylpropenal
A
1-(2-chlorovinyl)benzene
B
(E)-3-phenylacrylic acid
Conditions | Yield |
---|---|
With sodium chlorite; sodium dihydrogenphosphate; dihydrogen peroxide In water; acetonitrile at 10℃; for 1h; | A 2% B 95% |
trisodium tris(3-sulfophenyl)phosphine
phenylpropyolic acid
A
(E)-3-phenylacrylic acid
B
tris(natrium-m-sulfonatophenyl)phosphanoxid
Conditions | Yield |
---|---|
In water for 2h; Ambient temperature; | A 95% B n/a |
Conditions | Yield |
---|---|
With hydrogen; caesium carbonate In N,N-dimethyl-formamide at 85℃; for 16h; Catalytic behavior; Reagent/catalyst; Temperature; High pressure; diastereoselective reaction; | 95% |
With bis(1,5-cyclooctadiene)nickel (0); 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 0℃; under 760 Torr; for 2h; | 85% |
Stage #1: carbon dioxide; phenylacetylene With Triethoxysilane; [IMesCuF] In hexane at 70℃; for 12h; Inert atmosphere; Stage #2: With hydrogenchloride In hexane; dichloromethane; water at 20℃; for 0.25h; Inert atmosphere; regioselective reaction; | 44% |
Conditions | Yield |
---|---|
With phosphate buffer; Bacillus sublilis esterase In methanol; hexane at 37℃; for 24h; Product distribution; Further Variations:; Reagents; | 95% |
Conditions | Yield |
---|---|
palladium dichloride In water for 0.00555556h; Heck reaction; microwave irradiation; | 95% |
(E)-3-phenylacrylic acid
Conditions | Yield |
---|---|
Stage #1: (1-nosyl-5-nitroindol-3-yl)methyl cinnamate With 2-(N,N-dimethylamino)ethylthiol hydrochloride; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃; for 0.25h; Inert atmosphere; Stage #2: With hydrogenchloride In diethyl ether; water; acetonitrile Inert atmosphere; | 95% |
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 |
---|---|
In neat (no solvent) for 8h; Irradiation; | 100% |
for 120h; UV-irradiation; | 99% |
UV-irradiation; | 95% |
(E)-3-phenylacrylic acid
cinnamic anhydride
Conditions | Yield |
---|---|
With methanesulfonyl chloride; triethylamine In tetrahydrofuran at 0℃; for 1h; Inert atmosphere; | 100% |
With bis(trichloromethyl) carbonate; triethylamine In ethyl acetate at 0 - 20℃; | 97% |
With trimethylsilylethoxyacetylene In dichloromethane at 40℃; for 15h; | 96% |
Conditions | Yield |
---|---|
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃; Inert atmosphere; | 100% |
With thionyl chloride for 2h; Reflux; | 100% |
With thionyl chloride In N,N-dimethyl-formamide for 4h; Reflux; | 100% |
Conditions | Yield |
---|---|
With formic acid; palladium In methanol; water Ambient temperature; | 100% |
With hydrogen; palladium In ethyl acetate at 25℃; under 760.051 Torr; for 1h; | 100% |
With hydrogen; palladium in polystyrene In tetrahydrofuran at 25℃; under 760.051 Torr; for 1.5h; | 100% |
(E)-3-phenylacrylic acid
ethylene glycol
2-hydroxyethyl 3-(phenyl)-2-propenoate
Conditions | Yield |
---|---|
With sulfuric acid In toluene Heating; | 100% |
at 210℃; |
piperidine
(E)-3-phenylacrylic acid
(E)-3-phenyl-1-(piperidin-1-yl)-prop-2-en-1-one
Conditions | Yield |
---|---|
With dmap; benzenesulfonic anhydride In dichloromethane at 20℃; for 1h; | 100% |
Stage #1: (E)-3-phenylacrylic acid With 1,4-diaza-bicyclo[2.2.2]octane; bis(4,6-dimethoxy-1,3,5-triazin-2-yl) ether In acetonitrile at 0 - 5℃; for 0.666667h; Stage #2: piperidine In acetonitrile at 0 - 20℃; | 98% |
With dmap In dichloromethane at 20℃; for 1h; | 89% |
1 ,5-pentanediol
(E)-3-phenylacrylic acid
Cinnamic acid 1,5-pentane diol monoester
Conditions | Yield |
---|---|
With sulfuric acid In toluene Heating; | 100% |
Conditions | Yield |
---|---|
With sulfuric acid In toluene Heating; | 100% |
(E)-3-phenylacrylic acid
3-methocycatechol
2'-(difluoroboryloxy)-3'-hydroxy-4'-methoxychalcone
Conditions | Yield |
---|---|
With boron trifluoride In chloroform at 34℃; for 26h; | 100% |
(E)-3-phenylacrylic acid
N,O-dimethylhydroxylamine*hydrochloride
N-methoxy-N-methylcinnamamide
Conditions | Yield |
---|---|
With 4-methyl-morpholine In methanol at 20℃; | 100% |
Stage #1: (E)-3-phenylacrylic acid With 4-methyl-morpholine; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine In tetrahydrofuran at 20℃; for 1h; Stage #2: N,O-dimethylhydroxylamine*hydrochloride In tetrahydrofuran at 20℃; for 8h; Further stages.; | 97% |
With dmap; dicyclohexyl-carbodiimide Inert atmosphere; | 95.9% |
(E)-3-phenylacrylic acid
threo-3-Phenylpropionic acid-2,3-d2
Conditions | Yield |
---|---|
With deuterium; Ru(OCOCH3)2{(S)-2,2'-bis(diphenylphosphino)-1,1'-dinaphthyl)} In deuteromethanol at 20℃; under 2942.03 Torr; for 168h; Mechanism; hydrogenation of acrylic acid derivatives; | 100% |
With deuterium; Ru(OCOCH3)2{(S)-2,2'-bis(diphenylphosphino)-1,1'-dinaphthyl)} In deuteromethanol at 20℃; under 2942.03 Torr; for 168h; |
(E)-3-phenylacrylic acid
benzylamine
(E)-N-benzylcinnamamide
Conditions | Yield |
---|---|
With boric acid In toluene for 5h; Heating; | 100% |
N-methylpyridine-3-boronic acid In toluene for 27h; Heating; | 99% |
With borane-ammonia complex In 5,5-dimethyl-1,3-cyclohexadiene for 6h; Reflux; | 99% |
Conditions | Yield |
---|---|
With sulfuric acid In toluene Heating; | 100% |
(E)-3-phenylacrylic acid
diallyl dicarbonate
(E)-allyl cinnamate
Conditions | Yield |
---|---|
With dmap In tetrahydrofuran for 22h; | 100% |
(E)-3-phenylacrylic acid
allyl isopropenyl dicarbonate
(E)-allyl cinnamate
Conditions | Yield |
---|---|
With dmap In acetonitrile for 1h; Ambient temperature; | 100% |
Conditions | Yield |
---|---|
With caesium carbonate In acetonitrile for 2h; Heating; | 100% |
With cesium fluoride In acetonitrile for 1.5h; Heating; | 98% |
Conditions | Yield |
---|---|
With bromine In benzene for 4h; | 100% |
(E)-3-phenylacrylic acid
4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride
(E)-3-Phenyl-acrylic acid 4,6-dimethoxy-[1,3,5]triazin-2-yl ester
Conditions | Yield |
---|---|
In 1,2-dimethoxyethane at 0℃; for 3h; Condensation; | 100% |
(E)-3-phenylacrylic acid
3-phenylpropanoic acid-α,β-d2
Conditions | Yield |
---|---|
With aluminum oxide; rhodium(III) chloride; potassium deuteroformate for 0.05h; microwave irradiation; | 100% |
With 10% Pd/C; hydrogen; water-d2 In methanol at 20℃; for 6h; Reactivity; Reagent/catalyst; Solvent; chemoselective reaction; | 100% |
With samarium diiodide; water-d2 In tetrahydrofuran at 20℃; for 0.5h; | 77% |
With ethyl [2]alcohol; sodium In diethyl ether; mineral oil at 20℃; for 0.166667h; Inert atmosphere; | 35% |
(E)-3-phenylacrylic acid
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 0 - 20℃; for 17h; | 100% |
(E)-3-phenylacrylic acid
methyl 2-(bis(2,2,2-trifluoroethoxy)phosphoryl)-2-bromoacetate
Conditions | Yield |
---|---|
Stage #1: methyl 2-(bis(2,2,2-trifluoroethoxy)phosphoryl)-2-bromoacetate With 18-crown-6 ether; potassium tert-butylate In tetrahydrofuran; acetonitrile at -78℃; for 17h; Metallation; Stage #2: (E)-3-phenylacrylic acid In tetrahydrofuran at -78℃; for 5h; Horner-Wadsworth-Emmons reaction; Further stages.; | 100% |
Conditions | Yield |
---|---|
With dmap; benzenesulfonic anhydride In dichloromethane at 20℃; for 1h; | 100% |
(E)-3-phenylacrylic acid
rac-methylbenzylamine
(+/-)-3-phenyl-N-(1-phenylethyl)prop-2-enamide
Conditions | Yield |
---|---|
With dmap; benzenesulfonic anhydride In dichloromethane at 20℃; for 1h; | 100% |
With dmap In dichloromethane at 20℃; for 1h; | 94% |
With boric acid In toluene for 5h; Heating; | 74% |
phenylacetic acid
3-dimethylamino-1-(4-methylphenyl)propanamine
4-Methoxyphenylacetic acid
(E)-3-phenylacrylic acid
3-(4-methoxyphenyl)propanoic acid
(E)-3-(4-methoxyphenyl)acrylic acid
4-Trifluoromethylphenylacetic acid
3-<4'-(trifluoromethyl)phenyl>-2-propenoic acid
3-(4-trifluoromethylphenyl)propionic acid
phenylpropyolic acid
3-Phenylpropionic acid
Conditions | Yield |
---|---|
With polyvinylpyridine polymer-supported dimethylaminopyridine; PS-carbodiimide In dichloromethane at 20℃; for 96h; Polystyrene; | A 100% B 100% C 93% D 98% E 93% F 96% G 78% H 98% I 56% J 87% |
phenylacetic acid
3-dimethylamino-1-(2-naphthyl)propanamine
4-Methoxyphenylacetic acid
(E)-3-phenylacrylic acid
3-(4-methoxyphenyl)propanoic acid
(E)-3-(4-methoxyphenyl)acrylic acid
4-Trifluoromethylphenylacetic acid
3-<4'-(trifluoromethyl)phenyl>-2-propenoic acid
3-(4-trifluoromethylphenyl)propionic acid
phenylpropyolic acid
3-Phenylpropionic acid
Conditions | Yield |
---|---|
With polyvinylpyridine polymer-supported dimethylaminopyridine; PS-carbodiimide In dichloromethane at 20℃; for 96h; Polystyrene; | A 88% B 79% C 67% D 66% E 84% F 94% G 76% H 100% I 100% J 100% |
Reported in EPA TSCA Inventory.
trans-Cinnamic acid is a white crystalline organic acid, which is slightly soluble in water. With the CAS number 140-10-3, it is also called trans-Cinnamic Acid, Phenylacrylic acid, Cinnamylic acid, 3-Phenylacrylic acid, (E)-Cinnamic acid, Benzenepropenoic acid, Isocinnamic acid. It is obtained from oil of cinnamon, or from balsams such as storax.
Physical properties about trans-Cinnamic acid are: (1)ACD/LogP: 2.412; (2)ACD/LogD (pH 5.5): 1.22; (3)ACD/LogD (pH 7.4): -0.57; (4)ACD/BCF (pH 5.5): 2.60 ; (5)ACD/BCF (pH 7.4): 1.00; (6)ACD/KOC (pH 5.5): 31.72; (7)ACD/KOC (pH 7.4): 1.00; (8)#H bond acceptors: 2; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 2; (11)Index of Refraction: 1.616; (12)Molar Refractivity: 43.707 cm3; (13)Molar Volume: 125.035 cm3; (14)Polarizability: 17.327 10-24cm3; (15)Surface Tension: 49.7249984741211 dyne/cm; (16)Density: 1.185 g/cm3; (17)Flash Point: 189.53 °C ; (18)Enthalpy of Vaporization: 53.129 kJ/mol; (19)Boiling Point: 264.999 °C at 760 mmHg; (20)Vapour Pressure: 0.00499999988824129 mmHg at 25°C
Uses of trans-Cinnamic acid: This is a fragrant acid occurring in aromatic resins. Cinnamic acid and its derivatives are used as important components in flavours, perfumes, synthetic and pharmaceuticals, though its primary use is in the manufacturing of the methyl, ethyl, and benzyl esters for the perfume industry.
When you are using this chemical, please be cautious about it as the following:
1. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice;
2. Wear suitable protective clothing;
3. Wear suitable gloves and eye/face protection;
You can still convert the following datas into molecular structure:
(1)InChI=1S/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6+;
(2)InChIKey=WBYWAXJHAXSJNI-VOTSOKGWSA-N;
(3)Smilesc1(\C=C\C(O)=O)ccccc1;
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
bird - wild | LD50 | oral | 100mg/kg (100mg/kg) | Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983. |
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