140-10-3

Basic information

• Product Name: trans-Cinnamic acid
• Synonyms: (e)-2-propenoicaci;(E)-3-Phenyl-2-propenoic acid;(e)-3-phenyl-2-propenoicacid;(E)-Cinnamic acid;(e)-cinnamicaci;(e)-cinnamicacid;(E)-Zimtsαure;2-Propenoic acid, 3-phenyl-, (E)-
• CAS NO: 140-10-3
• Molecular Formula: C₉H₈O₂
• Molecular Weight: 148.16
• EINECS: 205-398-1
• Product Categories: Pharmaceutical Intermediates;Benzene derivatives;Aromatic Cinnamic Acids, Esters and Derivatives;Analytical Chemistry;Auxins;Biochemistry;Mass Spectrometry;Matrix Materials (MALDI-TOF-MS);Plant Growth Regulators;Highly Purified Reagents;Other Categories;Zone Refined Products;Matrices for MALDI Analysis;Aloe Vera;Aspalathus linearis (Rooibos tea);Building Blocks;C9;Carbonyl Compounds;Carboxylic Acids;Chemical Synthesis;Citrus aurantium (Seville orange);Curcuma longa (Turmeric);Hypericum perforatum (St John′Nutrition Research;Ocimum basilicum (Basil);Organic Building Blocks;Panax ginseng;Phytochemicals by Plant (Food/Spice/Herb);Piper methysticum (Kava);Proteomics;s wort);Vaccinium myrtillus (Bilberry);chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Inhibitors
• Mol File: 140-10-3.mol
• Article Data: 820

Chemical Properties

• Melting Point: 133 °C(lit.)
• Boiling Point: 300 °C(lit.)
• Flash Point: >230 °F
• Appearance: White to almost white/Crystalline Powder
• Density: 1.248
• Vapor Pressure: 0.005mmHg at 25°C
• Refractive Index: 1.5049 (estimate)
• Storage Temp.: Store at RT.
• Solubility: 0.4g/l
• PKA: 4.44(at 25℃)
• Water Solubility: 0.4 g/L (20 ºC)
• Merck: 14,2299
• BRN: 1905952
• CAS DataBase Reference: trans-Cinnamic acid(CAS DataBase Reference)
• NIST Chemistry Reference: trans-Cinnamic acid(140-10-3)
• EPA Substance Registry System: trans-Cinnamic acid(140-10-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 1
• RTECS: GD7850000
• TSCA: Yes
• Hazardous Substances Data: 140-10-3(Hazardous Substances Data)

Usage

Chemical Properties

White to almost white crystalline powder

Uses

Different sources of media describe the Uses of 140-10-3 differently. You can refer to the following data:
1. trans-Cinnamic acid is used in flavors, synthetic indigo and pharmaceuticals. It is involved in the production of methyl, ethyl and benzyl esters, which is used in the perfume industry. It serves as a precursor to the sweetener aspartame through enzyme-catalyzed amination to phenylalanine. It is a self-inhibitor produced by fungal spores to prevent germination. In addition, it is used to establish phenolic compounds by liquid chromatography, ultraviolet and mass spectrometry. It is utilized as a potential agent, thereby preventing lung tumor cells from metastasizing. Further, it induces intracellular release of calcium ions from the vacuole to the cytoplasm in order to trigger phytotoxicity in cucumber.
2. trans-Cinnamic acid was used to establish library of phenolic compounds by liquid chromatography/ultraviolet and mass spectrometry/mass spectrometry.

General Description

trans-Cinnamic acid is an α,β-unsaturated aromatic acid that can be used as a flavoring agent. It is mainly used to prepare ester derivatives that are used in perfume industry. trans-Cinnamic acid is the key volatile components of cinnamon essential oil.

Flammability and Explosibility

Notclassified

Biochem/physiol Actions

trans-cinnamic acid has inhibitory effect on phorbol-12-myristate-13-acetate-induced invasion of human lung adenocarcinoma A549 cells. It is a potential agent which can prevent lung tumor cells from metastasizing. It induces intracellular release of Ca2+ from the vacuole to the cytoplasm which triggers phytotoxicity in cucumber.

Purification Methods

Crystallise the acid from *benzene, CCl4, hot water, water/EtOH (3:1), or 20% aqueous EtOH. Dry it at 60o in vacuo. It is steam volatile. [Beilstein 9 IV 2002.]

InChI:InChI=1/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6-

Synthetic route

(E)-3-phenylpropenal (14371-10-9) → (E)-3-phenylacrylic acid (140-10-3)

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%

ethyl cinnamate (4192-77-2) → (E)-3-phenylacrylic acid (140-10-3)

Conditions	Yield
With barium dihydroxide In methanol at 80℃; for 2h;	100%
	98.5%
	98.5%

iodobenzene (591-50-4) + acrylic acid (79-10-7) → (E)-3-phenylacrylic acid (140-10-3)

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 (17719-70-9) → (E)-3-phenylacrylic acid (140-10-3)

Conditions	Yield
With water; dichloro bis(acetonitrile) palladium(II) at 40℃; for 1h;	100%

malonic acid (141-82-2) + benzaldehyde (100-52-7) → (E)-3-phenylacrylic acid (140-10-3)

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%

3-phenyl-propenal (104-55-2) → (E)-3-phenylacrylic acid (140-10-3)

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 (1866-31-5, 56289-55-5, 56289-56-6) → (E)-3-phenylacrylic acid (140-10-3)

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;

(2E)-3-phenyl-2-propen-1-ol (4407-36-7) → (E)-3-phenylacrylic acid (140-10-3)

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%

styrene (292638-84-7) + acrylic acid (79-10-7) → (E)-3-phenylacrylic acid (140-10-3)

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%

Sb(C6H5)4(OOCCHCHC6H5) → tetraphenylantimony(V) chloride (19638-17-6, 16894-68-1) + (E)-3-phenylacrylic acid (140-10-3)

Conditions	Yield
With aq. HCl	A 99% B n/a

erythro-2,3-dibromo-3-phenylpropanoic acid (6286-30-2, 31357-31-0, 54624-38-3, 91649-50-2, 99145-28-5, 113569-00-9, 113626-42-9) → (E)-3-phenylacrylic acid (140-10-3)

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%

benzaldehyde (100-52-7) + acetic acid (64-19-7) → (E)-3-phenylacrylic acid (140-10-3)

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 (92097-23-9) → (E)-3-phenylacrylic acid (140-10-3)

Conditions	Yield
With methanol; tetrakis(triphenylphosphine) palladium(0) In dichloromethane for 2h; Ambient temperature;	98%

iodobenzene (591-50-4) + acrylic acid methyl ester (292638-85-8) → (E)-3-phenylacrylic acid (140-10-3)

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.

acetic acid tert-butyl ester (540-88-5) + benzaldehyde (100-52-7) → (E)-3-phenylacrylic acid (140-10-3)

Conditions	Yield
Stage #1: acetic acid tert-butyl ester; benzaldehyde With titanium tetrachloride In dichloromethane for 0.5h; Stage #2: With triethylamine	98%

Methyl cinnamate (103-26-4) → (E)-3-phenylacrylic acid (140-10-3)

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 (65946-59-0) + benzaldehyde (100-52-7) → (E)-3-phenylacrylic acid (140-10-3)

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 (201486-55-7) → (E)-3-phenylacrylic acid (140-10-3)

Conditions	Yield
With lithium hydroxide; dihydrogen peroxide In tetrahydrofuran; water for 3.4h; Product distribution; other reag.; other solvent;	97%

tert-butyl cinnamate (14990-09-1) → tert-butyl nitrate (926-05-6) + (E)-3-phenylacrylic acid (140-10-3)

Conditions	Yield
With nitric acid In dichloromethane at 0℃; for 2h;	A 60% B 96%

tert-butyl cinnamate (14990-09-1) → (E)-3-phenylacrylic acid (140-10-3)

Conditions	Yield
With sulfuric acid In dichloromethane at 20℃; for 6h;	96%
With KSF clay In acetonitrile for 3h; Heating;	95%

bromobenzene (108-86-1) + acrylic acid (79-10-7) → (E)-3-phenylacrylic acid (140-10-3)

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%

4-((tert-butyldimethylsilyl)oxy)benzyl cinnamate → (E)-3-phenylacrylic acid (140-10-3)

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 0.5h;	96%

(E)-3-phenylpropenal (14371-10-9) → 1-(2-chlorovinyl)benzene (622-25-3) + (E)-3-phenylacrylic acid (140-10-3)

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 (63995-70-0) + phenylpropyolic acid (637-44-5) → (E)-3-phenylacrylic acid (140-10-3) + tris(natrium-m-sulfonatophenyl)phosphanoxid (98511-67-2)

Conditions	Yield
In water for 2h; Ambient temperature;	A 95% B n/a

carbon dioxide (124-38-9) + phenylacetylene (536-74-3) → (E)-3-phenylacrylic acid (140-10-3)

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%

(E)-cinnamic acid benzyl ester (103-41-3) → (E)-3-phenylacrylic acid (140-10-3)

Conditions	Yield
With phosphate buffer; Bacillus sublilis esterase In methanol; hexane at 37℃; for 24h; Product distribution; Further Variations:; Reagents;	95%

diphenyliodonium chloride (1483-72-3) + acrylic acid (79-10-7) → (E)-3-phenylacrylic acid (140-10-3)

Conditions	Yield
palladium dichloride In water for 0.00555556h; Heck reaction; microwave irradiation;	95%

(1-nosyl-5-nitroindol-3-yl)methyl cinnamate → (E)-3-phenylacrylic acid (140-10-3)

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%

methanol (67-56-1) + (E)-3-phenylacrylic acid (140-10-3) → Methyl cinnamate (103-26-4)

Conditions	Yield
With sulfuric acid at 65℃; for 16h;	100%
With sulfuric acid	100%
With ammonium cerium(IV) nitrate at 20℃; for 240h;	99%

(E)-3-phenylacrylic acid (140-10-3) → truxillic acid (490-20-0)

Conditions	Yield
In neat (no solvent) for 8h; Irradiation;	100%
for 120h; UV-irradiation;	99%
UV-irradiation;	95%

(E)-3-phenylacrylic acid (140-10-3) → cinnamic anhydride (21947-71-7)

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%

(E)-3-phenylacrylic acid (140-10-3) → Cinnamoyl chloride (102-92-1)

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%

(E)-3-phenylacrylic acid (140-10-3) → 3-Phenylpropionic acid (501-52-0)

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 (140-10-3) + ethylene glycol (107-21-1) → 2-hydroxyethyl 3-(phenyl)-2-propenoate (146604-63-9)

Conditions	Yield
With sulfuric acid In toluene Heating;	100%
at 210℃;

piperidine (110-89-4) + (E)-3-phenylacrylic acid (140-10-3) → (E)-3-phenyl-1-(piperidin-1-yl)-prop-2-en-1-one (5422-81-1, 27845-72-3)

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 (111-29-5) + (E)-3-phenylacrylic acid (140-10-3) → Cinnamic acid 1,5-pentane diol monoester (111917-09-0)

Conditions	Yield
With sulfuric acid In toluene Heating;	100%

Butane-1,4-diol (110-63-4) + (E)-3-phenylacrylic acid (140-10-3) → Cinnamic acid 1,4-butane diol monoester

Conditions	Yield
With sulfuric acid In toluene Heating;	100%

(E)-3-phenylacrylic acid (140-10-3) + 3-methocycatechol (934-00-9) → 2'-(difluoroboryloxy)-3'-hydroxy-4'-methoxychalcone (82964-29-2)

Conditions	Yield
With boron trifluoride In chloroform at 34℃; for 26h;	100%

(E)-3-phenylacrylic acid (140-10-3) + N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) → N-methoxy-N-methylcinnamamide (80783-99-9, 124931-15-3, 113474-86-5)

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 (140-10-3) → threo-3-Phenylpropionic acid-2,3-d2 (52760-22-2, 52760-23-3, 62015-11-6, 71806-58-1)

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 (140-10-3) + benzylamine (100-46-9) → (E)-N-benzylcinnamamide (57152-94-0, 104047-17-8, 5100-00-5)

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%

(E)-3-phenylacrylic acid (140-10-3) + trimethyleneglycol (504-63-2) → (E)-3-hydroxypropyl 3-phenylprop-2-enoate

Conditions	Yield
With sulfuric acid In toluene Heating;	100%

(E)-3-phenylacrylic acid (140-10-3) + diallyl dicarbonate (115491-93-5) → (E)-allyl cinnamate (1866-31-5, 56289-55-5, 56289-56-6)

Conditions	Yield
With dmap In tetrahydrofuran for 22h;	100%

(E)-3-phenylacrylic acid (140-10-3) + allyl isopropenyl dicarbonate (160788-62-5) → (E)-allyl cinnamate (1866-31-5, 56289-55-5, 56289-56-6)

Conditions	Yield
With dmap In acetonitrile for 1h; Ambient temperature;	100%

(E)-3-phenylacrylic acid (140-10-3) + ethyl iodide (75-03-6) → ethyl cinnamate (4192-77-2)

Conditions	Yield
With caesium carbonate In acetonitrile for 2h; Heating;	100%
With cesium fluoride In acetonitrile for 1.5h; Heating;	98%

(E)-3-phenylacrylic acid (140-10-3) → (E)-2,3-Dibromo-3-phenyl-acrylic acid (708-81-6)

Conditions	Yield
With bromine In benzene for 4h;	100%

(E)-3-phenylacrylic acid (140-10-3) + 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (3945-69-5) → (E)-3-Phenyl-acrylic acid 4,6-dimethoxy-[1,3,5]triazin-2-yl ester (345910-94-3)

Conditions	Yield
In 1,2-dimethoxyethane at 0℃; for 3h; Condensation;	100%

(E)-3-phenylacrylic acid (140-10-3) → 3-phenylpropanoic acid-α,β-d2 (188528-54-3)

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%

polyglycerol + (E)-3-phenylacrylic acid (140-10-3) → cinnamic acid polyglyceryl ester

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 0 - 20℃; for 17h;	100%

(E)-3-phenylacrylic acid (140-10-3) + methyl 2-(bis(2,2,2-trifluoroethoxy)phosphoryl)-2-bromoacetate (287481-44-1) → ethyl (2E,4E)-2-bromo-5-phenylpenta-2,4-dienoate

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%

(E)-3-phenylacrylic acid (140-10-3) + 3-Phenylpropan-1-amine (2038-57-5) → (E)-3-phenyl-N-(3-phenylpropyl)-2-propenamide

Conditions	Yield
With dmap; benzenesulfonic anhydride In dichloromethane at 20℃; for 1h;	100%

(E)-3-phenylacrylic acid (140-10-3) + rac-methylbenzylamine (618-36-0) → (+/-)-3-phenyl-N-(1-phenylethyl)prop-2-enamide (1004997-26-5)

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 (103-82-2) + 3-dimethylamino-1-(4-methylphenyl)propanamine (917351-49-6) + 4-Methoxyphenylacetic acid (104-01-8) + (E)-3-phenylacrylic acid (140-10-3) + 3-(4-methoxyphenyl)propanoic acid (1929-29-9) + (E)-3-(4-methoxyphenyl)acrylic acid (943-89-5) + 4-Trifluoromethylphenylacetic acid (32857-62-8) + 3-<4'-(trifluoromethyl)phenyl>-2-propenoic acid (2062-26-2, 87212-84-8, 16642-92-5) + 3-(4-trifluoromethylphenyl)propionic acid (53473-36-2) + phenylpropyolic acid (637-44-5) + 3-Phenylpropionic acid (501-52-0) → N-[3-dimethylamino-1-(4-methylphenyl)propyl]cinnamic amide + N-[3-dimethylamino-1-(4-methylphenyl)propyl]-3-phenylpropiolic amide + N-[3-dimethylamino-1-(4-methylphenyl)propyl]-2-phenylacetamide + N-[3-dimethylamino-1-(4-methylphenyl)propyl]-2-(4-trifluoromethylphenyl)acetamide + N-[3-dimethylamino-1-(4-methylphenyl)propyl]-2-(4-methoxyphenyl)acetamide + N-[3-dimethylamino-1-(4-methylphenyl)propyl]-3-phenylpropionamide + N-[3-dimethylamino-1-(4-methylphenyl)propyl]-3-(4-trifluoromethylphenyl)propionamide + N-[3-dimethylamino-1-(4-methylphenyl)propyl]-3-(4-methoxyphenyl)propionamide + N-[3-dimethylamino-1-(4-methylphenyl)propyl]-4-(trifluoromethyl)cinnamamide + N-[3-dimethylamino-1-(4-methylphenyl)propyl]-4-methoxycinnamamide

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%

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phenylacetic acid (103-82-2) + 3-dimethylamino-1-(2-naphthyl)propanamine (917351-50-9) + 4-Methoxyphenylacetic acid (104-01-8) + (E)-3-phenylacrylic acid (140-10-3) + 3-(4-methoxyphenyl)propanoic acid (1929-29-9) + (E)-3-(4-methoxyphenyl)acrylic acid (943-89-5) + 4-Trifluoromethylphenylacetic acid (32857-62-8) + 3-<4'-(trifluoromethyl)phenyl>-2-propenoic acid (2062-26-2, 87212-84-8, 16642-92-5) + 3-(4-trifluoromethylphenyl)propionic acid (53473-36-2) + phenylpropyolic acid (637-44-5) + 3-Phenylpropionic acid (501-52-0) → N-[3-dimethylamino-1-(2-naphthyl)propyl]-2-(4-trifluoromethylphenyl)acetamide + N-[3-dimethylamino-1-(2-naphthyl)propyl]-2-(4-methoxyphenyl)acetamide + N-[3-dimethylamino-1-(2-naphthyl)propyl]-2-phenylacetamide + N-[3-dimethylamino-1-(2-naphthyl)propyl]-3-phenylpropionamide + N-[3-dimethylamino-1-(2-naphthyl)propyl]-3-(4-trifluoromethylphenyl)propionamide + N-[3-dimethylamino-1-(2-naphthyl)propyl]-3-(4-methoxyphenyl)propionamide + N-[3-dimethylamino-1-(2-naphthyl)propyl]cinnamamide + N-[3-dimethylamino-1-(2-naphthyl)propyl]-4-(trifluoromethyl)cinnamamide + N-[3-dimethylamino-1-(2-naphthyl)propyl]-4-methoxycinnamamide + N-[3-dimethylamino-1-(2-naphthyl)propyl]-3-phenylpropiolamide

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%

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Upstream product

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• 14010-10-7 5-[(2E)-but-2-en-1-yl]-5-but-2-en-1-ylpyrimidine-2,4,6(1H,3H,5H)-trione 
• 1400994-91-3 5-Chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine 
• 14009-94-0 4-nitrophenyl N-acetylphenylalaninate 
• 1400-99-3 2-(5-{(3E)-34-tert-butyl-18-[(5-hydroperoxy-3,4-dihydroxytetrahydrofuran-2-yl)oxy]-9,11,13,15,17,21,25,29,33-nonahydroxy-2,4,20,32-tetramethyl-35-oxocyclohexatriacont-3-en-1-yl}-4-hydroxyhexyl)guanidine sulfate (salt) 
• 14009-92-8 AC-TRP-ONP 
• 1400987-00-9 [1,1':4',1'':3'',1''':4''',1''''-Quinquephenyl]-4,4''''-diamine, 5''-(4'-amino[1,1'-biphenyl]-4-yl)- 
• 14009-71-3 cis-linaloolpyranoxide,cis-6-ethenyltetrahydro-2,2,6-trimethylpyran-3-ol,cis-pyranoidlinalooloxide 
• 14009-70-2 18-Methyl Mestranol 
• 14009-58-6 Androst-5-ene-3,17-diol-17-propanoic acid lactone 
• 14009-42-8 3-[2-(Diethylamino)ethyl]-1H-indol-5-ol 

Downstream Products

• 1866-31-5 ALLYL CINNAMATE 
• 21211-07-4 METHYL 3-CHLOROBENZO[B]THIOPHENE-2-CARBOXYLATE 
• 21211-22-3 3-CHLOROBENZO[B]THIOPHENE-2-CARBOXYLIC ACID 
• 7786-61-0 4-Hydroxy-3-methoxystyrene 
• 21815-91-8 3-CHLOROBENZO[B]THIOPHENE-2-CARBONYL CHLORIDE 
• 103-26-4 Methyl cinnamate 
• 103-36-6 Ethyl cinnamate 
• 103890-78-4 Lacidipine 
• 103-95-7 3-(4-ISOPROPYLPHENYL)ISOBUTYRALDEHYDE 
• 104-54-1 Cinnamyl alcohol 
• 119-84-6 Cinnamic acid 
• 122-69-0 Cinnamyl cinnamate 
• 122-78-1 Phenylacetaldehyde 
• 21211-09-6 3-CHLOROBENZO[B]THIOPHENE-2-CARBOXAMIDE 
• 621-82-9 Cinnamic acid 
• 103-41-3 Benzyl cinnamate 
• 122-40-7 Amylcinnamaldehyde 
• 62524-21-4 3-CHLORO-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID HYDRAZIDE 

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