2495-37-6

Basic information

• Product Name: Benzyl methacrylate
• Synonyms: 2-methyl-2-propenoicaciphenylmethylester;2-Propenoic acid, 2-methyl-, phenylmethyl ester;2-Propenoicacid,2-methyl-,phenylmethylester;Benzyl 2-methylacrylate;BENZYL METHACRYLATE;METHACRYLIC ACID BENZYL ESTER;METHACRYLIC ACID BENZYL ESTER (STABILIZED WITH MEHQ) 98+%;Benzylmethacrylat
• CAS NO: 2495-37-6
• Molecular Formula: C₁₁H₁₂O₂
• Molecular Weight: 176.21
• EINECS: 219-674-4
• Product Categories: Acrylic Monomers;C10 to C11Monomers;Carbonyl Compounds;Esters;Methacrylate
• Mol File: 2495-37-6.mol
• Article Data: 29

Chemical Properties

• Melting Point: <25 °C
• Boiling Point: 95-98 °C4 mm Hg(lit.)
• Flash Point: 225 °F
• Appearance: colourless liquid
• Density: 1.04 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0262mmHg at 25°C
• Refractive Index: n20/D 1.512(lit.)
• Storage Temp.: 2-8°C(protect from light)
• Water Solubility: Insoluble in water.
• Sensitive: Light Sensitive
• Stability: Stable. Flammable. Incompatible with free-radical initiators, oxidizing agents, reducing agents. Avoid heat. Light-sensitive.
• BRN: 2045924
• CAS DataBase Reference: Benzyl methacrylate(CAS DataBase Reference)
• NIST Chemistry Reference: Benzyl methacrylate(2495-37-6)
• EPA Substance Registry System: Benzyl methacrylate(2495-37-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 1
• TSCA: Yes
• Hazardous Substances Data: 2495-37-6(Hazardous Substances Data)

Usage

Chemical Properties

colourless liquid

Uses

Benzyl methacrylate is an important raw material and intermediate used in organic synthesis, pharmaceuticals and agrochemicals.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C11H12O2/c1-9(2)11(12)13-8-10-6-4-3-5-7-10/h3-7H,1,8H2,2H3

Synthetic route

poly(methacrylic acid) (79-41-4) + benzyl alcohol (100-51-6) → benzyl methacrylate (2495-37-6)

Conditions	Yield
tetrachlorobis(tetrahydrofuran)hafnium(IV) In benzene for 40h; Heating;	99%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 4h;	90%
toluene-4-sulfonic acid In benzene for 15h; Heating;	85%

methacrylic acid methyl ester (80-62-6) + benzyl alcohol (100-51-6) → benzyl methacrylate (2495-37-6)

Conditions	Yield
With C2H3O3(1-)*C37H78N(1+) In hexane at 90℃; for 2h; Reagent/catalyst; Molecular sieve;	97%
With lanthanum (III) nitrate * water; 1,1,1-trioctyl-1-methylphosphonium methylcarbonate In hexane for 10h; Molecular sieve; Reflux;	80%

Methacryloyl chloride (920-46-7) + benzyl alcohol (100-51-6) → benzyl methacrylate (2495-37-6)

Conditions	Yield
With triethylamine at 0℃; Inert atmosphere; Microwave irradiation;	96%
With triethylamine In dichloromethane at 0℃;	62%
With triethylamine In dichloromethane at 0℃; Inert atmosphere;	50%

(1-Benzyloxy-2-chloro-2-methyl-cyclopropoxy)-trimethyl-silane (81171-49-5) → benzyl methacrylate (2495-37-6)

Conditions	Yield
With triethylamine In methanol for 6h; Heating;	91%
With triethylamine In methanol for 12h; Heating; Yield given;

benzyl 3-(dimethylamino)-2-methylpropanoate (1426060-15-2) → benzyl methacrylate (2495-37-6)

Conditions	Yield
With 2-chloro-4,6-dimethoxy-1 ,3,5-triazine; triethylamine In isopropyl alcohol at 20℃; for 0.25h; Eschenmoser Methylenation;	90%

benzoic acid (65-85-0) + 2-bromoisobutyric acid,benzyl ester (75107-16-3) → C18H18O4 + benzyl methacrylate (2495-37-6)

Conditions	Yield
With silver(l) oxide In water; acetonitrile at 100℃; for 24h;	A 89% B n/a

benzyl chloride (100-44-7) + Methacryloyl chloride (920-46-7) → benzyl methacrylate (2495-37-6)

Conditions	Yield
With dmap; caesium carbonate at 50℃; for 24h; Concentration;	89%

vinyl methacrylate (4245-37-8) + benzyl alcohol (100-51-6) → benzyl methacrylate (2495-37-6)

Conditions	Yield
With TBA7[γ-HGeW10O36] In acetonitrile at 39.84℃; for 0.0166667h;	83%

benzyl 2-(tripheny l-λ5phosphanylidene)propanoate (63613-50-3) → benzyl methacrylate (2495-37-6)

Conditions	Yield
With carbon dioxide; potassium tert-butylate In N,N-dimethyl-formamide at 100℃; under 760.051 Torr; for 12h;	83%

1,2-propanediene (463-49-0) + carbon monoxide (201230-82-2) + benzyl alcohol (100-51-6) → benzyl methacrylate (2495-37-6)

Conditions	Yield
dodecacarbonyl-triangulo-triruthenium at 80℃; under 22800 Torr; for 5h;	73%

benzyl 2-methyl-3-(methylthio)propanoate (94751-48-1) + methyl trifluoromethanesulfonate (333-27-7) → benzyl methacrylate (2495-37-6)

Conditions	Yield
In dichloromethane	65%

α-ethoxycarbonyloxy-isobutyric acid benzyl ester → benzyl methacrylate (2495-37-6)

Conditions	Yield
Destillation;

benzyl 2-hydroxy-2-methylpropanoate (19444-23-6) → benzyl methacrylate (2495-37-6)

Conditions	Yield
With phosphorus pentachloride In toluene at 80℃;

poly(methacrylic acid) (79-41-4) + benzyl chloride (100-44-7) → benzyl methacrylate (2495-37-6)

Conditions	Yield
With triethylamine In toluene at 75℃; Kinetics; Thermodynamic data; other reagents, solvents; influence of the nature of the solvent on the kinetics of the formation of benzyl methacrylate;

benzyl chloride (100-44-7) + sodium-compound of acetoacetanilide → benzyl methacrylate (2495-37-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: dimethylformamide / 160 °C 2: PCl5 / toluene / 80 °C View Scheme

1-benzyloxy-1-(trimethylsilyloxy)ethylene (81171-44-0) → benzyl methacrylate (2495-37-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: n-butyllithium / diethyl ether / -35 °C 2: triethylamine / methanol / 12 h / Heating View Scheme
Multi-step reaction with 2 steps 1: butyllithium / hexane; diethyl ether / -40 - -30 °C 2: 91 percent / triethylamine / methanol / 6 h / Heating View Scheme

Benzyl bromoacetate (5437-45-6) → benzyl methacrylate (2495-37-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: 60 percent / Zn 2: n-butyllithium / diethyl ether / -35 °C 3: triethylamine / methanol / 12 h / Heating View Scheme

Benzyl acetate (140-11-4) → benzyl methacrylate (2495-37-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) diisopropylamine, n-butyllithium / 1.) THF, hexane, -78 deg C, 30 min; 2.) -78 deg C, 15 min; room temp., 1 h 2: butyllithium / hexane; diethyl ether / -40 - -30 °C 3: 91 percent / triethylamine / methanol / 6 h / Heating View Scheme

benzyl 3-[(ethoxycarbonyl)oxy]-2-methyl-2-[(propionyloxy)methyl]propanoate → benzyl methacrylate (2495-37-6) + propionic acid (802294-64-0)

Conditions	Yield
at 626.84℃; Kinetics; Further Variations:; Temperatures;

toluene (108-88-3) → benzyl methacrylate (2495-37-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogen bromide; dihydrogen peroxide / water / 6 h / 5 - 10 °C 2: 4-methoxy-phenol / water / 8 h / 95 °C View Scheme

sodium methacrylate (5536-61-8) + benzyl bromide (100-39-0) → benzyl methacrylate (2495-37-6)

Conditions	Yield
With 4-methoxy-phenol In water at 95℃; for 8h;

carbon dioxide (124-38-9) + benzyl 2-(tripheny l-λ5phosphanylidene)propanoate (63613-50-3) → benzyl methacrylate (2495-37-6)

Conditions	Yield
With sodium t-butanolate In N,N-dimethyl-formamide at 100℃; under 760.051 Torr; for 12h; Schlenk technique; Sealed tube;	59 mg

benzyl methacrylate (2495-37-6) + α,α-dichloromethyl p-tolyl sulfoxide (37067-52-0) → 2-chloro-1-methyl-2-(toluene-4-sulfinyl)cyclopropanecarboxylic acid benzyl ester

Conditions	Yield
With sodium hexamethyldisilazane In tetrahydrofuran at -78 - 0℃; for 2h;	99%

benzyl methacrylate (2495-37-6) + α,α-dichloromethyl p-tolyl sulfoxide (37067-52-0) → C19H19ClO3S

Conditions	Yield
With sodium hexamethyldisilazane In tetrahydrofuran at -78 - 0℃; for 2h;	99%

tert.-butylhydroperoxide (75-91-2) + benzyl methacrylate (2495-37-6) + pivalaldehyde (630-19-3) → C19H30O4 (1415690-07-1)

Conditions	Yield
With iron(II) chloride In decane; acetonitrile at 85℃; for 1h; Inert atmosphere;	99%

benzyl methacrylate (2495-37-6) + methylphenylsilane (766-08-5) → C18H22O2Si

Conditions	Yield
With (tris(4,4-dimethyl-2-oxazolinyl)phenylborate)MgHB(C6F5)3 In benzene at 20℃; for 4h;	99%

benzyl methacrylate (2495-37-6) + 4-methylbenzo[d]oxadiazole → C19H19NO3

Conditions	Yield
With di-μ-acetato-bis(η4-1,5-cyclooctadiene)dirhodium(I); 4,4'-di-tert-butylbiphenyl; C46H50N2O4P2; cesium acetate In acetonitrile at 100℃; for 48h; Glovebox; Sealed tube; Inert atmosphere; enantioselective reaction;	98%
With di-μ-acetato-bis(η4-1,5-cyclooctadiene)dirhodium(I); C46H50N2O4P2; C14H17NO3; cesium acetate In acetonitrile at 100℃; for 48h; Glovebox; Sealed tube; Inert atmosphere; enantioselective reaction;	95%

benzyl methacrylate (2495-37-6) + trimethylpyruvic acid (815-17-8) → benzyl 2,4,4-trimethylpentanoate (114222-35-4)

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate In acetone at 25℃; for 3h; Inert atmosphere; Irradiation;	97%

benzyl methacrylate (2495-37-6) + glycine ethyl ester hydrochloride (623-33-6) → 5-benzyl 3-ethyl 5-methyl-4,5-dihydroisoxazole-3,5-dicarboxylate

Conditions	Yield
With tert.-butylnitrite; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; sodium hydrogencarbonate; zinc dibromide In tert-butyl methyl ether at 20℃; for 24h; Schlenk technique; Inert atmosphere; Sealed tube;	97%

benzyl methacrylate (2495-37-6) → benzyl pyruvate (18854-19-8)

Conditions	Yield
Stage #1: benzyl methacrylate With ozone In dichloromethane at -78℃; Stage #2: With Merrifield resin-bound piperidine In dichloromethane at 20℃; for 8h;	96%

benzyl methacrylate (2495-37-6) → benzyl 2-methylpropanoate (103-28-6)

Conditions	Yield
With 1,4-dioxane; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,2-bis-(dicyclohexylphosphino)ethane at 130℃; for 10h; Inert atmosphere; Sealed tube; chemoselective reaction;	96%
With hydrogen In methanol at 20℃; for 5h; chemoselective reaction;	92%
With palladium on activated charcoal; hydrogen In methanol at 20℃; for 24h; chemoselective reaction;	86%

Bromoform (75-25-2) + benzyl methacrylate (2495-37-6) → benzyl 2,2-dibromo-1-methylcyclopropylcarboxylate

Conditions	Yield
With benzyltriethylammonium bromide; sodium hydroxide at 20℃; for 4h;	93.6%

benzyl methacrylate (2495-37-6) + C16H28N2OSi → C24H32N2O3

Conditions	Yield
With tris(2,2'-bipyridyl)ruthenium dichloride In N,N-dimethyl-formamide at 25℃; for 12h; Schlenk technique; Sealed tube; Glovebox; Inert atmosphere; Irradiation;	93%

benzyl methacrylate (2495-37-6) → benzyl 2-hydroxy-2-methylpropanoate (19444-23-6)

Conditions	Yield
With phenylsilane; oxygen; bis(dipivaloylmethanato)manganese(II) In isopropyl alcohol at 0℃; under 760 Torr; for 1.5h;	92%
Multi-step reaction with 3 steps 1: triphenylphosphine; Stryker's reagent / toluene / 1 h / 20 °C / Inert atmosphere 2: tributylphosphine / toluene / 144 h / 20 °C / Inert atmosphere 3: N,N-dimethylaniline N-oxide / dichloromethane / 0 - 20 °C / Inert atmosphere View Scheme

1-iodocyclohexane (626-62-0) + benzyl methacrylate (2495-37-6) → benzyl 3-cyclohexyl-2-methylpropanoate

Conditions	Yield
With dimanganese decacarbonyl; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate In dimethyl sulfoxide at 20℃; for 24h; Inert atmosphere; Sealed tube; Irradiation;	92%

tert.-butylhydroperoxide (75-91-2) + benzyl methacrylate (2495-37-6) + benzaldehyde (100-52-7) → benzyl 2-(tert-butylperoxy)-2-methyl-4-oxo-4-phenylbutanoate (1415689-92-7)

Conditions	Yield
With iron(II) chloride In decane; acetonitrile at 85℃; for 1h; Concentration; Reagent/catalyst; Inert atmosphere;	91%

benzyl methacrylate (2495-37-6) + N-phenacylpyridinium bromide (16883-69-5) → benzyl 2-methyl-5-oxo-5-phenyl-2-(pyridin-2-yl)pentanoate

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 20℃; for 72h; Sealed tube; Irradiation; Inert atmosphere; regioselective reaction;	90%

chloroform (67-66-3) + benzyl methacrylate (2495-37-6) → benzyl 2,2-dichloro-1-methylcyclopropylcarboxylate

Conditions	Yield
With benzyltriethylammonium bromide; sodium hydroxide at 20℃; for 4h;	89.5%

benzyl methacrylate (2495-37-6) + 1,3-dioxoisoindolin-2-yl (tert-butoxycarbonyl)valinate → benzyl 4-((tert-butoxycarbonyl)amino)-2,5-dimethylhexanoate

Conditions	Yield
With eosin; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 18h; Irradiation; Green chemistry;	89%

ethylenebis(triphenylphosphine)platinum(0) (12120-15-9) + benzyl methacrylate (2495-37-6) → Pt(P(C6H5)3)2(CH2C(CH3)COOCH2C6H5) (186495-05-6)

Conditions	Yield
In toluene byproducts: C2H4; N2-atmosphere; stirring equimolar amts. for 2 h; cooling to 0°C, pptn. on addn. of petroleum ether, collection (filtration), washing (petroleum ether), drying (vac.);	88%

benzyl methacrylate (2495-37-6) + cyclohexyltrifluoro-λ4-borane potassium salt (446065-11-8) → benzyl 3-cyclohexyl-2-methylpropanoate

Conditions	Yield
With methanol; 9-(2-mesityl)-10-methylacridinium perchlorate In acetone at 20℃; for 24h; Irradiation;	88%

benzyl methacrylate (2495-37-6) → benzyl 2,3-dihydroxy-2-methylpropanoate

Conditions	Yield
With osmium(VIII) oxide; 4-methylmorpholine N-oxide In acetone; tert-butyl alcohol for 48h;	87%
With AD-mix-α In water; tert-butyl alcohol at 20℃; for 18h; Sharpless asymmetric dihydroxylation;	85%
With potassium permanganate; N-benzyl-N,N,N-triethylammonium chloride In acetone at -2 - 2℃; for 0.5h;	84%
Stage #1: benzyl methacrylate With C28H55N2(1+)*Cl(1-) In acetone at 20℃; for 0.166667h; Stage #2: With potassium permanganate In acetone at 0 - 5℃; for 2.17h;	83%

benzyl methacrylate (2495-37-6) + tetraethylammonium bis<α,α-bis(trifluoromethyl)benzenemethanolato(2-)-C2,O>cyclohexylsilicate (125764-09-2) → benzyl 3-cyclohexyl-2-methylpropanoate

Conditions	Yield
With 3,6‐di‐tert‐butyl‐9‐mesityl‐10‐phenylacridin‐10‐ium tetrafluoroborate In methanol; acetone at 23℃; for 3h; Irradiation;	87%

benzyl methacrylate (2495-37-6) + 3-methylbutyl tert-butylsulfamate → benzyl 6-((N-(tert-butyl)sulfamoyl)oxy)-2,4,4-trimethylhexanoate

Conditions	Yield
With potassium phosphate tribasic trihydrate In N,N-dimethyl-formamide at 25℃; for 48h; Inert atmosphere; Irradiation;	86%

benzyl methacrylate (2495-37-6) + benzyl-methyl-amine (103-67-3) → benzyl 2-methyl-3-[(phenylmethyl)amino]propionate (1148109-08-3)

Conditions	Yield
In glycerol at 100℃; for 5h; aza-Michael reaction;	85%

Upstream product

• 80-62-6 methacrylic acid methyl ester 
• 100-51-6 benzyl alcohol 
• 920-46-7 Methacryloyl chloride 
• 79-41-4 poly(methacrylic acid) 
• 19444-23-6 benzyl 2-hydroxy-2-methylpropanoate 
• 81171-49-5 (1-Benzyloxy-2-chloro-2-methyl-cyclopropoxy)-trimethyl-silane 
• 100-44-7 benzyl chloride 
• 94751-48-1 benzyl 2-methyl-3-(methylthio)propanoate 
• 333-27-7 methyl trifluoromethanesulfonate 
• 463-49-0 1,2-propanediene 
• 201230-82-2 carbon monoxide 
• 65-85-0 benzoic acid 
• 75107-16-3 2-bromoisobutyric acid,benzyl ester 
• 81171-44-0 1-benzyloxy-1-(trimethylsilyloxy)ethylene 

Downstream Products

• 91796-44-0 Benzyl 3-(phenylmethoxy)-2-methylpropanoate 
• 103-28-6 benzyl 2-methylpropanoate 
• 6640-85-3 benzyl 2-methylpentanoate 
• 205983-53-5 3-(3-carbethoxypiperidin-1-yl)-2-methylpropionic acid benzyl ester 
• 1241957-43-6 benzyl 2,2-difluoro-1-methylcyclopropanecarboxylate 
• 208192-24-9 C₂₂H₂₄O₄ 
• 1426060-15-2 benzyl 3-(dimethylamino)-2-methylpropanoate 
• 79-31-2 isobutyric Acid 

Relevant articles and documents

INFLUENCE OF SOLVENTS ON THE KINETICS OF THE REACTION OF BENZYL CHLORIDE WITH METHACRYLIC ACID IN THE PRESENCE OF TERTIARY AMINES

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Dehydrogenative Silylation of Alkenes for the Synthesis of Substituted Allylsilanes by Photoredox, Hydrogen-Atom Transfer, and Cobalt Catalysis

A synergistic catalytic method combining photoredox catalysis, hydrogen-atom transfer, and proton-reduction catalysis for the dehydrogenative silylation of alkenes was developed. With this approach, a highly concise route to substituted allylsilanes has been achieved under very mild reaction conditions without using oxidants. This transformation features good to excellent yields, operational simplicity, and high atom economy. Based on control experiments, a possible reaction mechanism is proposed.

Synthesis method of terminal olefin type compound

The invention discloses a synthesis method of a terminal olefin type compound. The synthesis method comprises the following steps: taking a phosphorus ylide compound as a raw material and carbon dioxide as a C1 synthon in an organic solvent; reacting in the presence of a reducing agent to prepare the terminal olefin type compound, wherein the mole ratio of the phosphorus ylide compound to the reducing agent is 1 to (1 to 6) and the pressure of carbon dioxide is 1 to 3atm. The synthesis method disclosed by the invention has the advantages of convenience for operation, moderate conditions, widesubstrate applicable range and high efficiency; the defects in the prior art are filled; the synthesis method takes the carbon dioxide as synthon and carbon dioxide can be effectively absorbed so thata greenhouse effect is effectively prevented.