3-Benzoylacrylic acid supplier

Name
3-BENZOYLACRYLIC ACID
EINECS 209-496-5
CAS No. 583-06-2
Article Data31
CAS DataBase
Density 1.238 g/cm³
Solubility Insoluble in water.
Melting Point 94-97 °C(lit.)
Formula C₁₀H₈O₃
Boiling Point 333.9 °C at 760 mmHg
Molecular Weight 176.172
Flash Point 170 °C
Transport Information UN 2811
Appearance Yellow to yellow-brown cryst. needles or powde
Safety 26-36
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Acrylicacid, 3-benzoyl- (6CI,7CI,8CI);Acrylic acid, b-benzoyl- (2CI);3-Benzoylacrylic acid;4-Oxo-4-phenylcrotonic acid;Benzoylacrylic acid;NSC 143;b-Benzoylacrylic acid;
PSA 54.37000
LogP 1.51010

Synthetic route

: 108-31-6
maleic anhydride

: 71-43-2
benzene

: 583-06-2
3-benzoylacrylic acid

Conditions

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

: 98-86-2
acetophenone

: 298-12-4
Glyoxilic acid

: 583-06-2
3-benzoylacrylic acid

Conditions

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

: 2243-53-0
styrylacetic acid

: 583-06-2
3-benzoylacrylic acid

Conditions

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

: 65245-10-5
2-hydroxy-4-oxo-4-phenyl-butyric acid

: 583-06-2
3-benzoylacrylic acid

Conditions

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

: 99389-54-5
4-hydroxy-4-phenylbut-2-enoic acid

: 583-06-2
3-benzoylacrylic acid

Conditions

Conditions	Yield
With iodine; sodium carbonate

: 53515-22-3
3-bromo-4-oxo-4-phenylbutanoic acid

: 583-06-2
3-benzoylacrylic acid

Conditions

Conditions	Yield
With sodium acetate; acetic acid

: (α-bromo-cis-cinnamic acid )-(4-oxo-4-phenyl-crotonic acid )-anhydride

: 64-19-7
acetic acid

A: 583-06-2
3-benzoylacrylic acid

B: 15894-30-1
(E)-2-Bromo-3-phenyl-acrylic acid

...Expand

: (α-bromo-trans-cinnamic acid )-(4-oxo-4-phenyl-crotonic acid )-anhydride

: 64-19-7
acetic acid

A: 583-06-2
3-benzoylacrylic acid

B: 15813-24-8
(Z)-2-bromo-3-phenylacrylic acid

...Expand

: 53515-22-3
3-bromo-4-oxo-4-phenylbutanoic acid

: 127-09-3
sodium acetate

: 64-19-7
acetic acid

: 583-06-2
3-benzoylacrylic acid

...Expand

: 108-31-6
maleic anhydride

: 95896-86-9
1-bromocyclohexa-1,4-diene

: 583-06-2
3-benzoylacrylic acid

Conditions

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

: 33093-73-1
4,4-Dimethoxy-4-phenyl-crotonsaeure-aethylester

: 583-06-2
3-benzoylacrylic acid

Conditions

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

: 15121-89-8, 20908-27-4, 17450-56-5
ethyl 3-benzoyl acrylate

: 583-06-2
3-benzoylacrylic acid

Conditions

Conditions	Yield
With hydrogenchloride; acetic acid Heating;

: 108-31-6
maleic anhydride

: 7446-70-0
aluminium trichloride

: 71-43-2
benzene

: 583-06-2
3-benzoylacrylic acid

...Expand

: 19522-28-2
(Z)-4-oxo-4-phenyl-but-2-enoic acid methyl ester

diluted natrium carbonate: diluted natrium carbonate

: 583-06-2
3-benzoylacrylic acid

: 2243-53-0
styrylacetic acid

: 7732-18-5
water

: 7553-56-2
iodine

natrium carbonate: natrium carbonate

: 583-06-2
3-benzoylacrylic acid

...Expand

: 7647-01-0
hydrogenchloride

: 19522-28-2
(Z)-4-oxo-4-phenyl-but-2-enoic acid methyl ester

A: 583-06-2
3-benzoylacrylic acid

B: 65245-10-5
2-hydroxy-4-oxo-4-phenyl-butyric acid

...Expand

: 7647-01-0
hydrogenchloride

: 14274-07-8
methyl trans-β-benzoylacrylate

A: 583-06-2
3-benzoylacrylic acid

B: 65245-10-5
2-hydroxy-4-oxo-4-phenyl-butyric acid

...Expand

: 7664-93-9
sulfuric acid

: 65245-10-5
2-hydroxy-4-oxo-4-phenyl-butyric acid

: 583-06-2
3-benzoylacrylic acid

: 63104-90-5
α-bromo-β-benzoylpropionic acid

natrium carbonate: natrium carbonate

: 583-06-2
3-benzoylacrylic acid

: 99389-54-5
4-hydroxy-4-phenylbut-2-enoic acid

: 7553-56-2
iodine

natrium carbonate: natrium carbonate

: 583-06-2
3-benzoylacrylic acid

Conditions

Conditions	Yield
at 20℃;

...Expand

: 64-17-5
ethanol

: 22221-93-8, 22221-94-9, 99074-11-0
β-benzoyl-acrylic acid-dibromide

: sodium thiosulfate

potassium iodide: potassium iodide

: 583-06-2
3-benzoylacrylic acid

...Expand

: 90798-09-7
α-chloro-β-benzoylpropionic acid

natrium carbonate: natrium carbonate

A: 7647-01-0
hydrogenchloride

B: 583-06-2
3-benzoylacrylic acid

...Expand

: 90798-09-7
α-chloro-β-benzoylpropionic acid

: 7732-18-5
water

A: 583-06-2
3-benzoylacrylic acid

B: 65245-10-5
2-hydroxy-4-oxo-4-phenyl-butyric acid

...Expand

: 19159-39-8
phenylglyoxal dimethylacetal

: 583-06-2
3-benzoylacrylic acid

Conditions

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

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

: 583-06-2
3-benzoylacrylic acid

: 110-91-8
morpholine

: 583-06-2
3-benzoylacrylic acid

: 21813-61-6
2-Morpholino-4-oxo-4-phenyl-butansaeure

Conditions

Conditions	Yield
In ethanol; toluene	97%
With benzene

: 583-06-2
3-benzoylacrylic acid

: 53515-22-3
3-bromo-4-oxo-4-phenylbutanoic acid

Conditions

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

: 110-89-4
piperidine

: 583-06-2
3-benzoylacrylic acid

: 101105-59-3
4-Oxo-4-phenyl-2-piperidino-butansaeure

Conditions

Conditions	Yield
In ethanol; toluene	93%
With benzene

: 583-06-2
3-benzoylacrylic acid

: 32316-92-0
naphthalene-2-boronic acid

: 42299-50-3, 53744-33-5
(2E)-1-phenyl-3-(2-naphthyl)-2-propen-1-one

Conditions

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

: 583-06-2
3-benzoylacrylic acid

: 5720-07-0
4-methoxyphenylboronic acid

: 22252-15-9
trans-4-methoxychalcone

Conditions

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

: 583-06-2
3-benzoylacrylic acid

: 21204-67-1
methyl (triphenylphosphoranylidene)acetate

: 2-Phenylacetyl-3-(triphenyl-λ5-phosphanylidene)-succinic acid 4-methyl ester

Conditions

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

: 583-06-2
3-benzoylacrylic acid

: 106-38-7
para-bromotoluene

: 22252-14-8, 72758-77-1, 4224-87-7
(E)-3-(4-methylphenyl)-1-phenyl-2-propen-1-one

Conditions

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

: 583-06-2
3-benzoylacrylic acid

: 104-88-1
4-chlorobenzaldehyde

: 60721-33-7
1-(4-chlorophenyl)-4-phenylbutane-1,4-dione

Conditions

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

: 583-06-2
3-benzoylacrylic acid

: 1099-45-2
ethyl (triphenylphosphoranylidene)acetate

: 2-Phenylacetyl-3-(triphenyl-λ5-phosphanylidene)-succinic acid 4-ethyl ester

Conditions

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

: 583-06-2
3-benzoylacrylic acid

: 181763-50-8
6-(4-Chloro-phenyl)-4-(2-methoxy-4-methyl-phenyl)-1H-pyrimidine-2-thione

: 181763-69-9
2-[4-(4-Chloro-phenyl)-6-(2-methoxy-4-methyl-phenyl)-pyrimidin-2-ylsulfanyl]-4-oxo-4-phenyl-butyric acid

Conditions

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

: 583-06-2
3-benzoylacrylic acid

: 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

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

: 583-06-2
3-benzoylacrylic acid

: 5798-75-4
Ethyl 4-bromobenzoate

: 87116-41-4
ethyl (E)-4-(3-oxo-3-phenylprop-1-en-1-yl)benzoate

Conditions

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

: 583-06-2
3-benzoylacrylic acid

: 49791-47-1
ammonium salt of N-o-anisylamino dithiocarbamic acid

: 1075256-86-8
3-(2-methoxyphenyl)-5-(2-oxo-2-phenylethyl)-2-thioxo-1,3-thiazolidin-4-one

Conditions

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

: 110-62-3
pentanal

: 583-06-2
3-benzoylacrylic acid

: 77588-52-4
1-Phenyl-1,4-octanedione

Conditions

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%

: 583-06-2
3-benzoylacrylic acid

: 108-94-1
cyclohexanone

: 54469-72-6
4-Oxo-2-(2-oxo-cyclohexyl)-4-phenyl-butyric acid

Conditions

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

: 583-06-2
3-benzoylacrylic acid

: 98-80-6
phenylboronic acid

: 614-47-1
1,3-diphenyl-propen-3-one

Conditions

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

: 109-01-3
1-methyl-piperazine

: 583-06-2
3-benzoylacrylic acid

: 35045-67-1
2-N-Methylpiperazino-4-oxo-4-phenyl-butansaeure

Conditions

Conditions	Yield
In ethanol; toluene	82%

: 98-01-1
furfural

: 583-06-2
3-benzoylacrylic acid

: 77588-51-3
1-(furan-2-yl)-4-phenylbutane-1,4-dione

Conditions

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

: 583-06-2
3-benzoylacrylic acid

: 249526-05-4
6-(4-Chloro-phenyl)-4-(4-methoxy-2-methyl-phenyl)-5,6-dihydro-1H-pyrimidine-2-thione

: 2-[4-(4-Chloro-phenyl)-6-(4-methoxy-2-methyl-phenyl)-4,5-dihydro-pyrimidin-2-ylsulfanyl]-4-oxo-4-phenyl-butyric acid

Conditions

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

: 583-06-2
3-benzoylacrylic acid

: 90798-09-7
α-chloro-β-benzoylpropionic acid

Conditions

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

: 583-06-2
3-benzoylacrylic acid

: 100-52-7
benzaldehyde

: 495-71-6
phenacylacetophenone

Conditions

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

: 583-06-2
3-benzoylacrylic acid

: 4559-70-0
Diphenylphosphine oxide

: 433942-28-0
β-benzoyl-α-(diphenylphosphoryl)propionic acid

Conditions

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

: 583-06-2
3-benzoylacrylic acid

: 99074-11-0
3-benzoyl-2,3-dibromopropionic acid

Conditions

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

: 583-06-2
3-benzoylacrylic acid

: 123-72-8
butyraldehyde

: 63297-52-9
1-phenylheptane-1,4-dione

Conditions

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%

: 583-06-2
3-benzoylacrylic acid

: 20913-05-7
(Benzoylmethylene)triphenylphosphorane

: 4-Oxo-4-phenyl-2-phenylacetyl-3-(triphenyl-λ5-phosphanylidene)-butyric acid

Conditions

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

: 188290-36-0
thiophene

: 583-06-2
3-benzoylacrylic acid

: 170874-98-3
4-Oxo-4-phenyl-2-thiophen-2-yl-butyric acid

Conditions

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

: 583-06-2
3-benzoylacrylic acid

: 99-90-1
para-bromoacetophenone

: 253597-40-9
(E)-3-(4-Acetylphenyl)-1-phenyl-prop-2-en-1-on

Conditions

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

: 2589-57-3
dimethyl 2,2'-azobis(isobutyrate)

: 583-06-2
3-benzoylacrylic acid

: (E)-methyl 2,2-dimethyl-5-oxo-5-phenylpent-3-enoate

Conditions

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%

3-Benzoylacrylic acid Specification

This chemical is called 2-Butenoic acid, 4-oxo-4-phenyl-, and it can also be named as Benzoylacrylic acid. With the molecular formula of C₁₀H₈O₃, its molecular weight is 176.17. The CAS registry number of this chemical is 583-06-2. Additionally, its product categories are Aromatic Cinnamic Acids, Esters and Derivatives.

Other characteristics of the 2-Butenoic acid, 4-oxo-4-phenyl- can be summarised as followings: (1)ACD/LogP: 1.59; (2)# of Rule of 5 Violations: 0; (3)ACD/BCF (pH 5.5): 1; (4)ACD/BCF (pH 7.4): 1; (5)ACD/KOC (pH 5.5): 1.52; (6)ACD/KOC (pH 7.4): 1; (7)#H bond acceptors: 3; (8)#H bond donors: 1; (9)#Freely Rotating Bonds: 3; (10)Polar Surface Area: 43.37 Å²; (11)Index of Refraction: 1.577; (12)Molar Refractivity: 47.16 cm³; (13)Molar Volume: 142.2 cm³; (14)Polarizability: 18.69×10^-24cm³; (15)Surface Tension: 51.5 dyne/cm; (16)Density: 1.238 g/cm³; (17)Flash Point: 170 °C; (18)Enthalpy of Vaporization: 60.89 kJ/mol; (19)Boiling Point: 333.9 °C at 760 mmHg; (20)Vapour Pressure: 5.23E-05 mmHg at 25°C.

Production method of this chemical: The 2-Butenoic acid, 4-oxo-4-phenyl- could be obtained by the reactants of benzene and maleic acid anhydride. This reaction needs the reagent of AlCl₃, and the solvent of CS₂. The yield is 60 %. In addition, this reaction should be taken at the temperature of 5 °C.

Uses of this chemical: The 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. The yield is 97 %.

When you are using this chemical, please be cautious about it as the following: This chemical is irritating to eyes, respiratory system and skin. You should wear suitable protective clothing if you use it. In case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
1.SMILES: O=C(\C=C\C(=O)O)c1ccccc1
2.InChI: InChI=1/C10H8O3/c11-9(6-7-10(12)13)8-4-2-1-3-5-8/h1-7H,(H,12,13)/b7-6+
3.InChIKey: PLPDHGOODMBBGN-VOTSOKGWBJ

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	oral	250mg/kg (250mg/kg)		United States Patent Document

Product Name

3-BENZOYLACRYLIC ACID

Synthetic route

3-Benzoylacrylic acid Specification

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