583-06-2

Basic information

• Product Name: 3-BENZOYLACRYLIC ACID
• Synonyms: (2E)-4-Oxo-4-phenyl-2-butenoic acid;3-benzoyl-acrylicaci;4-oxo-4-phenyl-2-butenoicaci;4-phenyl-4-oxo-2-butenoicacid;Acrylic acid, 3-benzoyl-;beta-Benzoylacrylsaeure;Crotonic acid, 4-oxo-4-phenyl-;BENZOYL ACRYLIC ACID
• CAS NO: 583-06-2
• Molecular Formula: C₁₀H₈O₃
• Molecular Weight: 176.17
• EINECS: 209-496-5
• Product Categories: Aromatic Cinnamic Acids, Esters and Derivatives
• Mol File: 583-06-2.mol
• Article Data: 11

Chemical Properties

• Melting Point: 94-97 °C(lit.)
• Boiling Point: 267.77°C (rough estimate)
• Flash Point: 170 °C
• Appearance: Yellow to yellow-brown cryst. needles or powde
• Density: 1.1958 (rough estimate)
• Vapor Pressure: 5.23E-05mmHg at 25°C
• Refractive Index: 1.5036 (estimate)
• Storage Temp.: 2-8°C
• PKA: 3.43±0.10(Predicted)
• Water Solubility: Insoluble in water.
• BRN: 1817876
• CAS DataBase Reference: 3-BENZOYLACRYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3-BENZOYLACRYLIC ACID(583-06-2)
• EPA Substance Registry System: 3-BENZOYLACRYLIC ACID(583-06-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• RTECS: EM9259050
• TSCA: Yes
• HazardClass: 6.1
• Hazardous Substances Data: 583-06-2(Hazardous Substances Data)

Usage

Chemical Properties

YELLOW TO YELLOW-BROWN CRYST. NEEDLES OR POWDER

Uses

2-Butenoic acid, 4-oxo-4-phenyl- could react with morpholine, and obtain the 2-morpholin-4-yl-4-oxo-4-phenyl-butyric acid. This reaction needs the solvent of toluene, ethanol.

InChI:InChI=1/C10H8O3/c11-9(6-7-10(12)13)8-4-2-1-3-5-8/h1-7H,(H,12,13)/p-1/b7-6+

Synthetic route

maleic anhydride (108-31-6) + benzene (71-43-2) → 3-benzoylacrylic acid (583-06-2)

Conditions	Yield
With aluminum (III) chloride at 80℃; for 0.5h;	85%
With aluminium trichloride In carbon disulfide at 5℃;	60%

acetophenone (98-86-2) + Glyoxilic acid (298-12-4) → 3-benzoylacrylic acid (583-06-2)

Conditions	Yield
With hydrogenchloride In water; acetic acid for 18h; Reflux;	81%
at 100 - 105℃; for 2h;

styrylacetic acid (2243-53-0) → 3-benzoylacrylic acid (583-06-2)

Conditions	Yield
With water; iodine; sodium carbonate; potassium iodide

2-hydroxy-4-oxo-4-phenyl-butyric acid (65245-10-5) → 3-benzoylacrylic acid (583-06-2)

Conditions	Yield
With sulfuric acid at 0℃; anschliessend in Eiswasser giessen;

4-hydroxy-4-phenylbut-2-enoic acid (99389-54-5) → 3-benzoylacrylic acid (583-06-2)

Conditions	Yield
With iodine; sodium carbonate

3-bromo-4-oxo-4-phenylbutanoic acid (53515-22-3) → 3-benzoylacrylic acid (583-06-2)

Conditions	Yield
With sodium acetate; acetic acid

(α-bromo-cis-cinnamic acid )-(4-oxo-4-phenyl-crotonic acid )-anhydride + acetic acid (64-19-7) → 3-benzoylacrylic acid (583-06-2) + (E)-2-Bromo-3-phenyl-acrylic acid (15894-30-1)

(α-bromo-trans-cinnamic acid )-(4-oxo-4-phenyl-crotonic acid )-anhydride + acetic acid (64-19-7) → 3-benzoylacrylic acid (583-06-2) + (Z)-2-bromo-3-phenylacrylic acid (15813-24-8)

3-bromo-4-oxo-4-phenylbutanoic acid (53515-22-3) + sodium acetate (127-09-3) + acetic acid (64-19-7) → 3-benzoylacrylic acid (583-06-2)

maleic anhydride (108-31-6) + 1-bromocyclohexa-1,4-diene (95896-86-9) → 3-benzoylacrylic acid (583-06-2)

Conditions	Yield
(i) AgSbF6, SO2, (ii) /BRN= 106909/; Multistep reaction;

4,4-Dimethoxy-4-phenyl-crotonsaeure-aethylester (33093-73-1) → 3-benzoylacrylic acid (583-06-2)

Conditions	Yield
With formic acid; sulfuric acid at 100℃; for 1h;

ethyl 3-benzoyl acrylate (15121-89-8, 20908-27-4, 17450-56-5) → 3-benzoylacrylic acid (583-06-2)

Conditions	Yield
With hydrogenchloride; acetic acid Heating;

maleic anhydride (108-31-6) + aluminium trichloride (7446-70-0) + benzene (71-43-2) → 3-benzoylacrylic acid (583-06-2)

(Z)-4-oxo-4-phenyl-but-2-enoic acid methyl ester (19522-28-2) + diluted natrium carbonate → 3-benzoylacrylic acid (583-06-2)

styrylacetic acid (2243-53-0) + water (7732-18-5) + iodine (7553-56-2) + natrium carbonate → 3-benzoylacrylic acid (583-06-2)

hydrogenchloride (7647-01-0) + (Z)-4-oxo-4-phenyl-but-2-enoic acid methyl ester (19522-28-2) → 3-benzoylacrylic acid (583-06-2) + 2-hydroxy-4-oxo-4-phenyl-butyric acid (65245-10-5)

hydrogenchloride (7647-01-0) + methyl trans-β-benzoylacrylate (14274-07-8) → 3-benzoylacrylic acid (583-06-2) + 2-hydroxy-4-oxo-4-phenyl-butyric acid (65245-10-5)

sulfuric acid (7664-93-9) + 2-hydroxy-4-oxo-4-phenyl-butyric acid (65245-10-5) → 3-benzoylacrylic acid (583-06-2)

α-bromo-β-benzoylpropionic acid (63104-90-5) + natrium carbonate → 3-benzoylacrylic acid (583-06-2)

4-hydroxy-4-phenylbut-2-enoic acid (99389-54-5) + iodine (7553-56-2) + natrium carbonate → 3-benzoylacrylic acid (583-06-2)

Conditions	Yield
at 20℃;

ethanol (64-17-5) + β-benzoyl-acrylic acid-dibromide (22221-93-8, 22221-94-9, 99074-11-0) + sodium thiosulfate + potassium iodide → 3-benzoylacrylic acid (583-06-2)

α-chloro-β-benzoylpropionic acid (90798-09-7) + natrium carbonate → hydrogenchloride (7647-01-0) + 3-benzoylacrylic acid (583-06-2)

α-chloro-β-benzoylpropionic acid (90798-09-7) + water (7732-18-5) → 3-benzoylacrylic acid (583-06-2) + 2-hydroxy-4-oxo-4-phenyl-butyric acid (65245-10-5)

phenylglyoxal dimethylacetal (19159-39-8) → 3-benzoylacrylic acid (583-06-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: benzene / 5.5 h / Heating 2: HCO2H, H2SO4 / 1 h / 100 °C View Scheme

(2R)-4-oxo-4-phenyl-2-{[(1R)-1-phenylethyl]amino}butanoic acid (861896-81-3) → 3-benzoylacrylic acid (583-06-2)

morpholine (110-91-8) + 3-benzoylacrylic acid (583-06-2) → 2-Morpholino-4-oxo-4-phenyl-butansaeure (21813-61-6)

Conditions	Yield
In ethanol; toluene	97%
With benzene

3-benzoylacrylic acid (583-06-2) → 3-bromo-4-oxo-4-phenylbutanoic acid (53515-22-3)

Conditions	Yield
With bromine In acetic acid at 60℃;	94%

piperidine (110-89-4) + 3-benzoylacrylic acid (583-06-2) → 4-Oxo-4-phenyl-2-piperidino-butansaeure (101105-59-3)

Conditions	Yield
In ethanol; toluene	93%
With benzene

3-benzoylacrylic acid (583-06-2) + naphthalene-2-boronic acid (32316-92-0) → (2E)-1-phenyl-3-(2-naphthyl)-2-propen-1-one (42299-50-3, 53744-33-5)

Conditions	Yield
With palladium diacetate; copper(II) acetate monohydrate; potassium carbonate In N,N-dimethyl-formamide at 120℃; Inert atmosphere;	90%

3-benzoylacrylic acid (583-06-2) + 4-methoxyphenylboronic acid (5720-07-0) → trans-4-methoxychalcone (22252-15-9)

Conditions	Yield
With palladium diacetate; copper(II) acetate monohydrate; potassium carbonate In N,N-dimethyl-formamide at 120℃; Inert atmosphere;	89%

3-benzoylacrylic acid (583-06-2) + methyl (triphenylphosphoranylidene)acetate (21204-67-1) → 2-Phenylacetyl-3-(triphenyl-λ5-phosphanylidene)-succinic acid 4-methyl ester

Conditions	Yield
In benzene for 6h; other β-aroylacrylic acid or cinnamic acid, other phosphorane;	88%
In benzene for 6h; Heating;	88%

3-benzoylacrylic acid (583-06-2) + para-bromotoluene (106-38-7) → (E)-3-(4-methylphenyl)-1-phenyl-2-propen-1-one (22252-14-8, 72758-77-1, 4224-87-7)

Conditions	Yield
With sodium acetate; palladium diacetate; Tri(p-tolyl)phosphine In N,N-dimethyl-formamide at 120℃; for 4h; Inert atmosphere;	87%

3-benzoylacrylic acid (583-06-2) + 4-chlorobenzaldehyde (104-88-1) → 1-(4-chlorophenyl)-4-phenylbutane-1,4-dione (60721-33-7)

Conditions	Yield
With sodium carbonate; triethylamine; 3,4-dimethyl-5-(2-hydroxyethyl)thiazolium iodide In ethanol at 80℃; for 6h;	86%

3-benzoylacrylic acid (583-06-2) + ethyl (triphenylphosphoranylidene)acetate (1099-45-2) → 2-Phenylacetyl-3-(triphenyl-λ5-phosphanylidene)-succinic acid 4-ethyl ester

Conditions	Yield
In benzene for 6h; Heating;	85%

3-benzoylacrylic acid (583-06-2) + 6-(4-Chloro-phenyl)-4-(2-methoxy-4-methyl-phenyl)-1H-pyrimidine-2-thione (181763-50-8) → 2-[4-(4-Chloro-phenyl)-6-(2-methoxy-4-methyl-phenyl)-pyrimidin-2-ylsulfanyl]-4-oxo-4-phenyl-butyric acid (181763-69-9)

Conditions	Yield
With piperidine In benzene for 6h; Heating;	85%

3-benzoylacrylic acid (583-06-2) + 1-(4-thioxo-3,4-dihydroquinazolin-2-yl)heptadecane-1-sodium sulfonate → sodium 4-oxo-4-phenyl-2-[2-(1-sulfoheptadecyl)quinazolin-4-ylsulfanyl]butanoic acid

Conditions	Yield
In benzene at 20℃; for 48h;	85%
With piperidine In benzene at 20℃; for 48h;	85%

3-benzoylacrylic acid (583-06-2) + Ethyl 4-bromobenzoate (5798-75-4) → ethyl (E)-4-(3-oxo-3-phenylprop-1-en-1-yl)benzoate (87116-41-4)

Conditions	Yield
With sodium acetate; palladium diacetate; Tri(p-tolyl)phosphine In N,N-dimethyl-formamide at 120℃; for 4h; Inert atmosphere;	85%

3-benzoylacrylic acid (583-06-2) + ammonium salt of N-o-anisylamino dithiocarbamic acid (49791-47-1) → 3-(2-methoxyphenyl)-5-(2-oxo-2-phenylethyl)-2-thioxo-1,3-thiazolidin-4-one (1075256-86-8)

Conditions	Yield
In ethanol at 20℃; for 0.5h;	84%

pentanal (110-62-3) + 3-benzoylacrylic acid (583-06-2) → 1-Phenyl-1,4-octanedione (77588-52-4)

Conditions	Yield
With sodium carbonate; triethylamine; 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride In ethanol at 80℃; for 6h;	83%

3-benzoylacrylic acid (583-06-2) + cyclohexanone (108-94-1) → 4-Oxo-2-(2-oxo-cyclohexyl)-4-phenyl-butyric acid (54469-72-6)

Conditions	Yield
With potassium hydroxide In ethanol at 30 - 40℃; for 1h;	83%

3-benzoylacrylic acid (583-06-2) + phenylboronic acid (98-80-6) → 1,3-diphenyl-propen-3-one (614-47-1)

Conditions	Yield
With palladium diacetate; copper(II) acetate monohydrate; potassium carbonate In N,N-dimethyl-formamide at 120℃; Inert atmosphere;	83%

1-methyl-piperazine (109-01-3) + 3-benzoylacrylic acid (583-06-2) → 2-N-Methylpiperazino-4-oxo-4-phenyl-butansaeure (35045-67-1)

Conditions	Yield
In ethanol; toluene	82%

furfural (98-01-1) + 3-benzoylacrylic acid (583-06-2) → 1-(furan-2-yl)-4-phenylbutane-1,4-dione (77588-51-3)

Conditions	Yield
With sodium carbonate; triethylamine; 3,4-dimethyl-5-(2-hydroxyethyl)thiazolium iodide In ethanol at 80℃; for 6h;	82%

3-benzoylacrylic acid (583-06-2) + 6-(4-Chloro-phenyl)-4-(4-methoxy-2-methyl-phenyl)-5,6-dihydro-1H-pyrimidine-2-thione (249526-05-4) → 2-[4-(4-Chloro-phenyl)-6-(4-methoxy-2-methyl-phenyl)-4,5-dihydro-pyrimidin-2-ylsulfanyl]-4-oxo-4-phenyl-butyric acid

Conditions	Yield
With piperidine In benzene for 6h; Heating;	82%

3-benzoylacrylic acid (583-06-2) → α-chloro-β-benzoylpropionic acid (90798-09-7)

Conditions	Yield
With hydrogenchloride at 20℃; for 72h;	81%
With hydrogenchloride; acetic acid
With hydrogenchloride

3-benzoylacrylic acid (583-06-2) + benzaldehyde (100-52-7) → phenacylacetophenone (495-71-6)

Conditions	Yield
With sodium carbonate; triethylamine; 3,4-dimethyl-5-(2-hydroxyethyl)thiazolium iodide In ethanol at 80℃; for 6h;	81%

3-benzoylacrylic acid (583-06-2) + Diphenylphosphine oxide (4559-70-0) → β-benzoyl-α-(diphenylphosphoryl)propionic acid (433942-28-0)

Conditions	Yield
In benzene for 6h; Heating;	81%

3-benzoylacrylic acid (583-06-2) → 3-benzoyl-2,3-dibromopropionic acid (99074-11-0)

Conditions	Yield
With bromine In acetic acid at 20℃;	80%
With bromine In chloroform at 20℃; for 3h;	40.64%
With chloroform; bromine

3-benzoylacrylic acid (583-06-2) + butyraldehyde (123-72-8) → 1-phenylheptane-1,4-dione (63297-52-9)

Conditions	Yield
With sodium carbonate; triethylamine; 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride In ethanol at 80℃; for 6h;	80%

3-benzoylacrylic acid (583-06-2) + (Benzoylmethylene)triphenylphosphorane (20913-05-7) → 4-Oxo-4-phenyl-2-phenylacetyl-3-(triphenyl-λ5-phosphanylidene)-butyric acid

Conditions	Yield
In ethyl acetate for 10h; Heating;	80%

thiophene (188290-36-0) + 3-benzoylacrylic acid (583-06-2) → 4-Oxo-4-phenyl-2-thiophen-2-yl-butyric acid (170874-98-3)

Conditions	Yield
In benzene for 5h; Heating;	80%

3-benzoylacrylic acid (583-06-2) + para-bromoacetophenone (99-90-1) → (E)-3-(4-Acetylphenyl)-1-phenyl-prop-2-en-1-on (253597-40-9)

Conditions	Yield
With sodium acetate; palladium diacetate; Tri(p-tolyl)phosphine In N,N-dimethyl-formamide at 120℃; for 4h; Inert atmosphere;	80%

dimethyl 2,2'-azobis(isobutyrate) (2589-57-3) + 3-benzoylacrylic acid (583-06-2) → (E)-methyl 2,2-dimethyl-5-oxo-5-phenylpent-3-enoate

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; silver orthophosphate; copper(II) nitrate trihydrate In 5,5-dimethyl-1,3-cyclohexadiene at 100℃; for 8h; Inert atmosphere;	80%

Upstream product

• 108-31-6 maleic anhydride 
• 71-43-2 benzene 
• 2243-53-0 styrylacetic acid 
• 65245-10-5 2-hydroxy-4-oxo-4-phenylbutanoic acid 
• 99389-54-5 4-hydroxy-4-phenylbut-2-enoic acid 
• 53515-22-3 3-bromo-4-oxo-4-phenylbutanoic acid 
• 64-19-7 acetic acid 
• 127-09-3 sodium acetate 
• 95896-86-9 1-bromocyclohexa-1,4-diene 
• 33093-73-1 4,4-Dimethoxy-4-phenyl-crotonsaeure-aethylester 
• 15121-89-8 ethyl 3-benzoyl acrylate 
• 7446-70-0 aluminium trichloride 
• 19522-28-2 (Z)-4-oxo-4-phenyl-but-2-enoic acid methyl ester 
• 7732-18-5 water 

Downstream Products

• 62577-84-8 2-anilino-4-oxo-4-phenyl-butyric acid 
• 2166-31-6 6-phenylpyridazin-3(2H)-one 
• 7345-02-0 5-benzoylmethyl-3-benzyl-2-thioxo-4-thiazolidinone 
• 56428-54-7 3-(benzoyl)-2'.6'-dimethyl-4'-nitroacrylanilide 
• 56428-53-6 3-(benzoyl)-2'.6'-dibromoacrylanilide 
• 56428-52-5 3-(benzoyl)-2'.4'.5'.6'-tetrachloroacrylanilide 
• 15121-89-8 ethyl 3-benzoyl acrylate 
• 56428-40-1 3-(benzoyl)-4'-trifluormethylacrylanilide 
• 100373-00-0 2-methylamino-4-oxo-4-phenyl-butyric acid 
• 6627-28-7 4-phenyl-4-phenylhydrazono-crotonic acid 
• 61652-16-2 4-phenyl quinoline 2-carboxylic acid 
• 100024-67-7 di-γ lactone of enolized diphenacylmaleic acid 
• 2051-95-8 succinylbenzene 
• 99074-11-0 3-benzoyl-2,3-dibromopropionic acid 

Relevant articles and documents

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Photoinduced, Copper-Promoted Regio- and Stereoselective Decarboxylative Alkylation of α,β-Unsaturated Acids with Alkyl Iodides

The first example of UV light-induced, copper-catalyzed regio- and stereoselective decarboxylative coupling of α,β-unsaturated acids with alkyl iodides was reported. Under standard conditions, the 1°, 2°, and 3° alkyl iodides proceeded smoothly with the E-selective alkenes obtained in uniformly good yields and high stereoselectivities.

Synthesis of 1,5-benzodiazepine derivatives using p-toluenesulfonic acid as catalyst

A series of substituted ethyl 4-oxo-4-phenylbut-2-enoates were prepared and reacted with substituted o-phenylenediamine, undergone Michael addition reactions and cyclodehydration to provide novel 4-phenyl-2,3-dihydro-1,5-benzodiazepine-2-carboxylate derivatives with excellent yields. The synthetic protocol fulfilled many green-chemical requirements by using simple catalyst p-toluenesulfonic acid as activator and ethanol as solvent at room temperature.