2-Benzylacrylic acid supplier

Name
2-Benzylacrylic acid
EINECS 219-673-9
CAS No. 5669-19-2
Article Data58
CAS DataBase
Density 1.12 g/cm³
Solubility
Melting Point 66-68 °C
Formula C₁₀H₁₀O₂
Boiling Point 326.1 °C at 760 mmHg
Molecular Weight 162.188
Flash Point 230.1 °C
Transport Information
Appearance White Solid
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Hydrocinnamicacid, a-methylene- (6CI,8CI);2-Methylene-3-phenylpropanoicacid;NSC 192640;a-Benzylacrylic acid;a-Methylenebenzenepropanoicacid;
PSA 37.30000
LogP 1.86990

Synthetic route

: 20593-63-9
2-Benzylacrylic acid ethyl ester

: 5669-19-2
2-Benzyl-2-propenoic acid

Conditions

Conditions	Yield
With lithium hydroxide In tetrahydrofuran; water for 15h; Heating;	100%
With ethanol; sodium hydroxide In dichloromethane at 10 - 20℃; for 3.5h; Time; Reflux;	92.8%
With potassium hydroxide In methanol for 18h;	80%

: 50-00-0
formaldehyd

: 616-75-1
2-benzylmalonic acid

: 5669-19-2
2-Benzyl-2-propenoic acid

Conditions

Conditions	Yield
With diethylamine for 5h; Mannich reaction;	98%
With diethylamine In ethyl acetate at 0℃; for 3h; Reflux;	90%
With diethylamine In ethyl acetate for 4h; Inert atmosphere; Reflux;	87%

: 616-75-1
2-benzylmalonic acid

: 5669-19-2
2-Benzyl-2-propenoic acid

Conditions

Conditions	Yield
Stage #1: 2-benzylmalonic acid With formaldehyd; diethylamine In ethyl acetate at 0 - 20℃; for 1.5h; Heating / reflux; Stage #2: With hydrogenchloride; water at 10℃;	90%
Stage #1: 2-benzylmalonic acid With formaldehyd; diethylamine In ethyl acetate Stage #2: With potassium hydroxide
Multi-step reaction with 2 steps 1: concentrated ammonia View Scheme

: 109481-98-3
(Z)-3-Phenyl-2-trimethylsilanylmethyl-acrylic acid ethyl ester

A: 5669-19-2
2-Benzyl-2-propenoic acid

B: 1895-97-2
2-methyl-3-phenylacrylic acid

Conditions

Conditions	Yield
With potassium hydroxide; water In methanol for 3h; Reflux;	A 12% B 87%

: (2-Methoxycarbonyl-3-phenyl-propyl)-trimethyl-ammonium; iodide

: 5669-19-2
2-Benzyl-2-propenoic acid

Conditions

Conditions	Yield
With sodium hydroxide at 100℃; for 2h;	80%

: 358382-80-6
5-benzyl-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxane-4,6-dione

: 5669-19-2
2-Benzyl-2-propenoic acid

Conditions

Conditions	Yield
With hydrogen bromide In water; acetic acid for 2h; Heating;	76%

: diethyl 2-benzyl-2(hydroxymethyl)malonate

: 5669-19-2
2-Benzyl-2-propenoic acid

Conditions

Conditions	Yield
With hydrogen bromide; acetic acid at 90℃; for 18h;	72.4%
With hydrogen bromide; acetic acid In water at 80℃; for 72h;

: 2495-35-4
benzylacrylate

: 5669-19-2
2-Benzyl-2-propenoic acid

Conditions

Conditions	Yield
With potassium hydroxide In methanol	66%

: 3070-71-1
methyl 2-benzylacrylate

: 5669-19-2
2-Benzyl-2-propenoic acid

Conditions

Conditions	Yield
With sodium hydroxide In methanol for 20h; Ambient temperature;	65%
With potassium hydroxide In ethanol Heating;
With lithium hydroxide monohydrate; water In tetrahydrofuran at 70℃; for 3h;

: 109481-98-3
(Z)-3-Phenyl-2-trimethylsilanylmethyl-acrylic acid ethyl ester

A: 1039704-09-0
(2Z)-3-phenyl-2-[(trimethylsilyl)methyl]prop 2-enoic acid

B: 5669-19-2
2-Benzyl-2-propenoic acid

C: 1895-97-2
2-methyl-3-phenylacrylic acid

Conditions

Conditions	Yield
With potassium hydroxide; water In methanol for 0.333333h; Reflux;	A 19% B 13% C 64%

...Expand

: 28769-48-4
α-benzylacrylonitrile

: 5669-19-2
2-Benzyl-2-propenoic acid

Conditions

Conditions	Yield
With sulfuric acid In water at 130℃; for 15h;	62%
With hydrogenchloride
With potassium hydroxide In 2-ethoxy-ethanol Heating;

: 30457-88-6
2-benzyl-2-propenal

: 5669-19-2
2-Benzyl-2-propenoic acid

Conditions

Conditions	Yield
With sodium chlorite; sodium phosphate In water; tert-butyl alcohol at 20℃; for 0.5h;	36%

: 97-65-4
2-methylenesuccinic acid

: 100-34-5
benzene diazonium chloride

: 5669-19-2
2-Benzyl-2-propenoic acid

Conditions

Conditions	Yield
With water; sodium acetate; copper dichloride Bestrahlen des Reaktionsprodukts in Gegenwart von Brom in Aether und CHCl3;

: 861356-96-9
benzyl-piperidinomethyl-malonic acid

: 5669-19-2
2-Benzyl-2-propenoic acid

: 408308-23-6
aminomethyl-benzyl-malonic acid

: 5669-19-2
2-Benzyl-2-propenoic acid

Conditions

Conditions	Yield
With water

: 69858-92-0
benzyl-methoxymethyl-malonic acid

: 5669-19-2
2-Benzyl-2-propenoic acid

Conditions

Conditions	Yield
With hydrogenchloride
With sulfuric acid at 170 - 175℃;

: 408308-33-8
benzyl-methylaminomethyl-malonic acid

: 5669-19-2
2-Benzyl-2-propenoic acid

: 24643-58-1
2-benzyl-2-carboxy-3-(dimethylamino)propionic acid

: 5669-19-2
2-Benzyl-2-propenoic acid

Conditions

Conditions	Yield
Thermolysis;
beim Schmelzen im Vakuum;

: allylaminomethyl-benzyl-malonic acid

: 5669-19-2
2-Benzyl-2-propenoic acid

: 855653-03-1
benzyl-methanesulfonylmethyl-malonic acid diethyl ester

: 5669-19-2
2-Benzyl-2-propenoic acid

Conditions

Conditions	Yield
With sodium hydroxide

: 871882-45-0
2,2'-dibenzyl-2,2'-(2-aza-propanediyl)-di-malonic acid

: 5669-19-2
2-Benzyl-2-propenoic acid

: 78763-98-1
2-(1-Benzyl-vinyl)-4,4-dimethyl-4,5-dihydro-oxazole

: 5669-19-2
2-Benzyl-2-propenoic acid

Conditions

Conditions	Yield
With hydrogenchloride; water; acetic acid Heating; Yield given;

(+-)-2-benzyl-2-methanesulfonylmethyl-3-oxo-butyric acid ethyl ester: (+-)-2-benzyl-2-methanesulfonylmethyl-3-oxo-butyric acid ethyl ester

: 5669-19-2
2-Benzyl-2-propenoic acid

Conditions

Conditions	Yield
With potassium hydroxide

: 15719-64-9, 15719-76-3, 97762-63-5
methylammonium carbonate

<β-bromo-allyl>-benzene: <β-bromo-allyl>-benzene

: 5669-19-2
2-Benzyl-2-propenoic acid

Conditions

Conditions	Yield
With diethyl ether; magnesium

methoxymethyl-benzyl-malonic acid ester: methoxymethyl-benzyl-malonic acid ester

: 5669-19-2
2-Benzyl-2-propenoic acid

Conditions

Conditions	Yield
With hydrogenchloride; water; acetic acid

: 7647-01-0
hydrogenchloride

: 69858-92-0
benzyl-methoxymethyl-malonic acid

: 5669-19-2
2-Benzyl-2-propenoic acid

: 7647-01-0
hydrogenchloride

: 69858-85-1
benzyl-methoxymethyl-malonic acid diethyl ester

: 7732-18-5
water

: 64-19-7
acetic acid

: 5669-19-2
2-Benzyl-2-propenoic acid

...Expand

: disodium carbaprephenate

A: 5669-19-2
2-Benzyl-2-propenoic acid

B: C11H8O4(2-)*2Na(1+)

Conditions

Conditions	Yield
With 50 mmol/l Tris*HCl buffer; Bacillus subtilis chorismate mutase at 30℃; pH=8.6; Product distribution; Further Variations:; Reagents;

: 607-81-8
diethyl 2-benzylmalonate

: 5669-19-2
2-Benzyl-2-propenoic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: KOH / aq. methanol 2.1: p-formaldehyde; diethylamine / ethyl acetate 2.2: aq. KOH View Scheme
Multi-step reaction with 2 steps 1: KOH / ethanol / 4 h / 0 - 20 °C 2: Et3N / H2O / Heating View Scheme
Multi-step reaction with 2 steps 1: water; potassium hydroxide / ethanol / 10 h / 20 °C 2: dimethyl amine / Reflux View Scheme
Multi-step reaction with 2 steps 1: sodium hydroxide; water / 5 h / Reflux 2: diethylamine / ethyl acetate / 3 h / 0 °C / Reflux View Scheme
Multi-step reaction with 2 steps 1: sodium hydroxide / methanol; water / 20 °C / Inert atmosphere 2: diethylamine / ethyl acetate / 4 h / Inert atmosphere; Reflux View Scheme

: 67-56-1
methanol

: 5669-19-2
2-Benzyl-2-propenoic acid

: 3070-71-1
methyl 2-benzylacrylate

Conditions

Conditions	Yield
With thionyl chloride at 0 - 20℃; for 18h;	100%
With boron trifluoride diethyl etherate for 14h; Heating;	94%

: 5669-19-2
2-Benzyl-2-propenoic acid

: 18107-18-1
diazomethyl-trimethyl-silane

: 3070-71-1
methyl 2-benzylacrylate

Conditions

Conditions	Yield
In methanol; hexane; benzene at 20℃; for 0.5h;	100%
	89%

: 5669-19-2
2-Benzyl-2-propenoic acid

: 88320-94-9
2-benzylpropenoyl chloride

Conditions

Conditions	Yield
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane for 1.5h;	100%
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 15℃; for 2h; Solvent; Temperature; Reagent/catalyst; Industrial scale;	99.4%
With thionyl chloride at 20℃; for 3h;	96%

: 5669-19-2
2-Benzyl-2-propenoic acid

: 507-09-5
thioacetic acid

: 91702-98-6
3-acetylthio-2-benzylpropanoic acid

Conditions

Conditions	Yield
In dichloromethane for 1152h;	99%
In tetrahydrofuran Heating;	96%
In benzene Heating;	77%

: 5669-19-2
2-Benzyl-2-propenoic acid

: 14367-67-0
2-methyl-3-phenylpropionic acid

Conditions

Conditions	Yield
With C54H72IrNP(1+)*C32H12BF24(1-); hydrogen; caesium carbonate In methanol at 45℃; under 4500.45 Torr; for 0.25h; Pressure; Glovebox;	99%
With disodium hydrogen phosphite pentahydrate; phosphite dehydrogenase; water; nicotinamide adenine dinucleotide phosphate; ene-reductase 36 at 25℃; pH=6.5; Catalytic behavior; Reagent/catalyst; pH-value; Temperature; Enzymatic reaction; enantioselective reaction;	99%
With C32H12BF24(1-)*C54H71IrNP(1+); hydrogen; caesium carbonate In methanol at 45℃; for 4h; optical yield given as %ee; enantioselective reaction;	98%
Stage #1: 2-Benzyl-2-propenoic acid With hydrogen; caesium carbonate; [(Sa-DTB-SIPHOX)Ir(COD)]BARF In methanol at 20℃; under 4500.45 Torr; for 12h; Stage #2: With hydrogenchloride In water pH=< 3; Product distribution / selectivity;	94%

: 5669-19-2
2-Benzyl-2-propenoic acid

: 1009-67-2, 5628-72-8, 14367-54-5, 14367-67-0
2-methyl-3-phenylpropionic acid

Conditions

Conditions	Yield
With C48H50Cl4N2O2P2Ru3; hydrogen; sodium hydrogencarbonate In methanol at 20℃; under 3750.38 Torr; for 24h; Autoclave; enantioselective reaction;	99%

: 5669-19-2
2-Benzyl-2-propenoic acid

: 86396-02-3
2-(phenyl-λ3-iodaneylidene)cyclohexane-1,3-dione

: 1000697-64-2
3-benzyl-7,8-dihydro-2H-chromene-2,5(6H)-dione

Conditions

Conditions	Yield
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; sodium acetate at 80℃; for 12h; Catalytic behavior; Mechanism; Temperature; Reagent/catalyst; Sealed tube;	99%
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; sodium acetate at 80℃; for 9h; Temperature; Reagent/catalyst;	99%

: 5669-19-2
2-Benzyl-2-propenoic acid

: 86396-05-6
(2,6-dioxo-4-phenylcyclohexyl)phenyliodonium inner salt

: 3-benzyl-7-phenyl-7,8-dihydro-2H-chromene-2,5(6H)-dione

Conditions

Conditions	Yield
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; sodium acetate at 80℃; for 12h;	98%

: 5669-19-2
2-Benzyl-2-propenoic acid

: 507-09-5
thioacetic acid

: 149603-85-0
2-acetylthio-3-phenyl-propionic acid

Conditions

Conditions	Yield
In CaCl2	95%

: 5669-19-2
2-Benzyl-2-propenoic acid

: 82860-53-5
2-hydroxy-N,N-diiso-propylbenzamide

: 2-(N,N-diisopropylcarbamoyl)phenyl 2-methylene-3-phenylpropionate

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In toluene at 80℃; for 9h;	95%

: 5669-19-2
2-Benzyl-2-propenoic acid

: 501-65-5
diphenyl acetylene

: 3-benzyl-5,6-diphenyl-2H-pyran-2-one

Conditions

Conditions	Yield
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; tetrabutylammonium acetate In methanol at 60℃; for 12h; Electrochemical reaction;	95%
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver carbonate at 80℃; for 8h;	60%

: 5669-19-2
2-Benzyl-2-propenoic acid

: N-(cyclopentylsulfinyl)benzamide

: 2-benzyl-3-cyclopentylpropanoic acid

Conditions

Conditions	Yield
With dipotassium hydrogenphosphate; [Ir(ppy)2(dtbbpy)]PF6 In acetone at 0 - 40℃; for 6h; Michael Addition; Inert atmosphere; Irradiation;	93%

: 5669-19-2
2-Benzyl-2-propenoic acid

: 1-(prop-2-yn-1-yloxy)-(1,1'-biphenyl)-4(1H)-one

: (Z)-2-benzyl-4-((E)-5-oxo-7a-phenyl-3a,4,5,7a-tetrahydrobenzofuran-3(2H)-ylidene)but-2-enoic acid

Conditions

Conditions	Yield
With Cp*Rh(OAc)2·H2O In 1,2-dichloro-ethane at 60℃; for 9h; stereoselective reaction;	92%

: 5669-19-2
2-Benzyl-2-propenoic acid

: 1-(prop-2-yn-1-yloxy)-(1,1'-biphenyl)-4(1H)-one

: C20H20O4

Conditions

Conditions	Yield
With (pentamethylcyclopentadienyl)*Rh(OAc)2 In 1,2-dichloro-ethane at 60℃; for 9h;	92%

: 5669-19-2
2-Benzyl-2-propenoic acid

: 2,4-dimethyl-4-(prop-2-yn-1-yloxy)cyclohexa-2,5-dien-1-one

: (Z)-2-benzyl-4-((E)-6,7a-dimethyl-5-oxo-3a,4,5,7a-tetrahydrobenzofuran-3(2H)-ylidene)but-2-enoic acid

Conditions

Conditions	Yield
With Cp*Rh(OAc)2·H2O In 1,2-dichloro-ethane at 60℃; for 9h; stereoselective reaction;	91%

: 5669-19-2
2-Benzyl-2-propenoic acid

: 4'-bromo-1-(prop-2-yn-1-yloxy)-[1,1'-biphenyl]-4(1H)-one

: (Z)-2-benzyl-4-((E)-7a-(4-bromophenyl)-5-oxo-3a,4,5,7a-tetrahydrobenzofuran-3(2H)-ylidene)but-2-enoic acid

Conditions

Conditions	Yield
With Cp*Rh(OAc)2·H2O In 1,2-dichloro-ethane at 60℃; for 9h; stereoselective reaction;	91%

: 5669-19-2
2-Benzyl-2-propenoic acid

: 2,4-dimethyl-4-(prop-2-yn-1-yloxy)cyclohexa-2,5-dien-1-one

: C21H22O4

Conditions

Conditions	Yield
With (pentamethylcyclopentadienyl)*Rh(OAc)2 In 1,2-dichloro-ethane at 60℃; for 9h;	91%

: 5669-19-2
2-Benzyl-2-propenoic acid

: 1009-67-2
2-methyl-3-phenylpropanoic acid

Conditions

Conditions	Yield
With phenylsilane; C12H23N2O2P In tetrahydrofuran at 23℃; for 2h;	91%
With hydrogen

: 5669-19-2
2-Benzyl-2-propenoic acid

: 865703-11-3
2-benzyl-3-(hydroxyhydrophosphoryl)propanoic acid

Conditions

Conditions	Yield
With bis(trimethylsilyl)phosphonite In dichloromethane at 0 - 20℃; for 25h; Inert atmosphere;	91%

: 507-09-5
thioacetic acid

: 5669-19-2
2-Benzyl-2-propenoic acid

: 91702-98-6
3-acetylthio-2-benzylpropanoic acid

Conditions

Conditions	Yield
at 100℃; for 2h;	90%

: 5669-19-2
2-Benzyl-2-propenoic acid

: 7-methyl-7-(prop-2-yn-1-yloxy)-1,2,3,7-tetrahydro-4H-inden-4-one

: (2Z,4E)-2-benzyl-4-(8b-methyl-5-oxo-4,5,6,7,8,8b-hexahydro-2H-indeno[4,5-b]furan-3(3aH)-ylidene)but-2-enoic acid

Conditions

Conditions	Yield
With Cp*Rh(OAc)2·H2O In 1,2-dichloro-ethane at 60℃; for 9h; stereoselective reaction;	90%

: 5669-19-2
2-Benzyl-2-propenoic acid

: 7-methyl-7-(prop-2-yn-1-yloxy)-1,2,3,7-tetrahydro-4H-inden-4-one

: C23H24O4

Conditions

Conditions	Yield
With (pentamethylcyclopentadienyl)*Rh(OAc)2 In 1,2-dichloro-ethane at 60℃; for 9h;	90%

: 5669-19-2
2-Benzyl-2-propenoic acid

: 86396-03-4
(2,6-dioxo-4-methylcyclohexyl)phenyliodonium inner salt

: 3-benzyl-7-methyl-7,8-dihydro-2H-chromene-2,5(6H)-dione

Conditions

Conditions	Yield
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; sodium acetate at 80℃; for 12h;	90%

: 5669-19-2
2-Benzyl-2-propenoic acid

: 7480-35-5, 13286-59-4, 74165-73-4, 126456-43-7, 136030-00-7, 140632-19-5, 140632-20-8
(1S,2R)-1-amino-2-indanol

: 872703-52-1
2-benzyl-N-[(1S,2R)-2-hydroxy-indan-1-yl]acrylamide

Conditions

Conditions	Yield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine	89%
Stage #1: 2-Benzyl-2-propenoic acid With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In ethyl acetate at 20℃; for 0.5h; Stage #2: (1S,2R)-1-amino-2-indanol In ethyl acetate at 20℃;	68%

: 5669-19-2
2-Benzyl-2-propenoic acid

: 4-butyl-4-(prop-2-yn-1-yloxy)cyclohexa-2,5-dien-1-one

: (Z)-2-benzyl-4-((E)-7a-butyl-5-oxo-3a,4,5,7a-tetrahydrobenzofuran-3(2H)-ylidene)but-2-enoic acid

Conditions

Conditions	Yield
With Cp*Rh(OAc)2·H2O In 1,2-dichloro-ethane at 60℃; for 9h; stereoselective reaction;	88%

: 5669-19-2
2-Benzyl-2-propenoic acid

: tert-butyl 4-(benzamidosulfinyl)piperidine-1-carboxylate

: 2-benzyl-3-(1-(tert-butoxycarbonyl)piperidin-4-yl)propanoic acid

Conditions

Conditions	Yield
With dipotassium hydrogenphosphate; [Ir(ppy)2(dtbbpy)]PF6 In acetone at 0 - 40℃; for 5h; Michael Addition; Inert atmosphere; Irradiation;	87%

2-Benzylacrylic acid Specification

The CAS registry number of 2-Benzyl acrylic acid is 5669-19-2. The IUPAC name is 2-benzylprop-2-enoic acid. In addition, the molecular formula is C₁₀H₁₀O₂. What's more, it is a kind of white solid and belongs to the classes of Racecadotril; Aliphatics; Aromatics. It can be used as pharmaceutical intermediates and raw materials in organic synthesis. Besides, it should be stored in sealed container, and put in a cool and dry place.

Physical properties about this chemical are: (1)ACD/LogP: 2.50; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.44; (4)ACD/BCF (pH 5.5): 4.06; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 47.41; (7)ACD/KOC (pH 7.4): 1; (8)#H bond acceptors: 2; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 3; (11)Polar Surface Area: 26.3 Å²; (12)Index of Refraction: 1.551; (13)Molar Refractivity: 46.2 cm³; (14)Molar Volume: 144.7 cm³; (15)Polarizability: 18.31 ×10^-24cm³; (16)Surface Tension: 42.8 dyne/cm; (17)Density: 1.12 g/cm³; (18)Flash Point: 230.1 °C; (19)Enthalpy of Vaporization: 59.99 kJ/mol; (20)Boiling Point: 326.1 °C at 760 mmHg; (21)Vapour Pressure: 8.97E-05 mmHg at 25°C.

Preparation of 2-Benzyl acrylic acid: it can be prepared by a-Benzylacrylsaeuremethylester. This reaction will need reagent aq. NaOH and solvent methanol. The reaction time is 20 hours with ambient temperature. The yield is about 65%.

2-Benzyl acrylic acid can be prepared by a-Benzylacrylsaeuremethylester

Uses of 2-Benzyl acrylic acid: it can react with thioacetic acid to get 2-acetylsulfanylmethyl-3-phenyl-propionic acid. This reaction is a kind of addition reaction. It will need solvent tetrahydrofuran. The reaction time is 18 hours at reaction temperature of 50 °C.

2-Benzyl acrylic acid can react with thioacetic acid to get 2-acetylsulfanylmethyl-3-phenyl-propionic acid

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(O)\C(=C)Cc1ccccc1
(2)InChI: InChI=1/C10H10O2/c1-8(10(11)12)7-9-5-3-2-4-6-9/h2-6H,1,7H2,(H,11,12)
(3)InChIKey: RYNDYESLUKWOEE-UHFFFAOYAD

Product Name

2-Benzylacrylic acid

Synthetic route

2-Benzylacrylic acid Specification

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