96-05-9

Basic information

• Product Name: Allyl methacrylate
• Synonyms: 2-Propenoicacid, 2-methyl-, 2-propenyl ester (9CI);Methacrylic acid, allyl ester(6CI,8CI);Allyl alcohol, methacrylate (6CI);2-Methyl-2-propenoic acid 2-propenyl ester;Acryester A;NSC 18597;2-Propenoic acid,2-methyl-, 2-propen-1-yl ester
• CAS NO: 96-05-9
• Molecular Formula: C₇H₁₀O₂
• Molecular Weight: 126.1531
• EINECS: 202-473-0
• Mol File: 96-05-9.mol
• Article Data: 14

Chemical Properties

• Melting Point: -65℃
• Boiling Point: 138.588 °C at 760 mmHg
• Flash Point: 33.889 °C
• Appearance: clear liquid
• Density: 0.917 g/cm³
• Vapor Pressure: 6.68mmHg at 25°C
• Refractive Index: 1.43
• Water Solubility: 4 g/L (20℃)
• CAS DataBase Reference: Allyl methacrylate(CAS DataBase Reference)
• NIST Chemistry Reference: Allyl methacrylate(96-05-9)
• EPA Substance Registry System: Allyl methacrylate(96-05-9)

Safety Data

• Hazard Codes: T:Toxic;;
• Statements: R10:; R21/22:; R23:; R50:
• Safety Statements: S36/37:; S45:; S61:
• Hazardous Substances Data: 96-05-9(Hazardous Substances Data)

Usage

General Description

Allyl methacrylate is a chemical compound used in the manufacturing of plastics, coatings, adhesives, and sealants. It is a colorless liquid with a pungent odor and is highly flammable. Allyl methacrylate is classified as an irritant to the skin, eyes, and respiratory system and may cause skin sensitization. It is also considered a potential environmental hazard due to its low biodegradability and potential to bioaccumulate in aquatic organisms. Despite its potential hazards, allyl methacrylate is widely used in various industrial applications due to its ability to improve the performance and properties of polymers.

InChI:InChI=1/C7H10O2/c1-4-5-9-7(8)6(2)3/h4H,1-2,5H2,3H3

Synthetic route

poly(methacrylic acid) (79-41-4) + Allyl acetate (591-87-7) → allyl methacrylate (96-05-9)

Conditions	Yield
With [Ir(1,5-cyclooctadiene)2]PF6 In toluene at 100℃; for 5h;	92%

2,3-Epoxypropyl methacrylate (106-91-2) → allyl methacrylate (96-05-9)

Conditions	Yield
With Silphos; iodine In N,N-dimethyl-formamide at 20℃; for 3h;	90%
With zirconium(IV) chloride; sodium iodide In acetonitrile for 0.0166667h; Heating;	88%
With bis(cyclopentadienyl)titanium dichloride; magnesium In tetrahydrofuran for 12h; Ambient temperature;	87%

allyl 2-((tert-butyl(1-(diethoxyphosphoryl)-2,2-dimethylpropyl)amino)oxy)-2-methylpropanoate (1393670-68-2) → allyl methacrylate (96-05-9) + diethyl (1-(tert-butyl((4,4-dimethyl-5-oxotetrahydrofuran-3-yl)methoxy)amino)-2,2-dimethylpropyl)phosphonate (1393670-72-8)

Conditions	Yield
In tert-butyl alcohol at 120℃; for 2h; Sealed tube;	A n/a B 50%

2,3-Epoxypropyl methacrylate (106-91-2) → 2-methyl-acrylic acid 3-chloro-2-iodo-propyl ester + allyl methacrylate (96-05-9)

Conditions	Yield
Stage #1: 2,3-Epoxypropyl methacrylate With N-chloro-succinimide; triphenylphosphine In acetonitrile at 20℃; Stage #2: With N-iodo-succinimide; triphenylphosphine In acetonitrile for 10h; Heating;	A 44% B n/a

α-allyloxy-isobutyric acid allyl ester (874487-06-6) → allyl methacrylate (96-05-9)

Conditions	Yield
at 60℃; mit Oxalsaeure, ZnCl2 oder besser P2O5;

α-acetoxy-isobutyric acid allyl ester (408318-09-2) → allyl methacrylate (96-05-9)

Conditions	Yield
at 475℃; Pyrolysis;

α-acetoxy-isobutyric acid allyl ester (408318-09-2) → allyl methacrylate (96-05-9) + acetic acid (64-19-7)

Conditions	Yield
at 475℃; Kontaktzeit ca.4.7 sec.Pyrolysis;

poly(methacrylic acid) (79-41-4) + allyl alcohol (107-18-6) → allyl methacrylate (96-05-9)

Conditions	Yield
With sulfuric acid
With toluene-4-sulfonic acid In toluene Heating;
With dmap; dicyclohexyl-carbodiimide In dichloromethane Inert atmosphere;

2-allyloxy-2-methylpropanoic acid (17859-93-7) + allyl alcohol (107-18-6) → allyl methacrylate (96-05-9) + α-allyloxy-isobutyric acid allyl ester (874487-06-6)

Conditions	Yield
With sulfuric acid; tannic acid

allyl alcohol (107-18-6) + methacrylic acid methyl ester (80-62-6) → allyl methacrylate (96-05-9)

Conditions	Yield
With sodium methylate; 2-hydroxyresorcinol
With oxygen; 4-methoxy-phenol; hydroquinone; zirconium(IV) acetylacetonate at 70 - 117℃; Product distribution / selectivity; Reflux;

allyl 2-hydroxyisobutyrate (19444-21-4) → allyl methacrylate (96-05-9)

Conditions	Yield
With phosphorus pentachloride In toluene at 80℃;
Multi-step reaction with 2 steps 1: H3PO4 / 80 - 110 °C 2: 475 °C / Pyrolysis View Scheme

α-allyloxy-isobutyric acid allyl ester (874487-06-6) + P2O5 → allyl methacrylate (96-05-9)

Conditions	Yield
at 60℃;

2-allyloxy-2-methylpropanoic acid (17859-93-7) → allyl methacrylate (96-05-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: concentrated H2SO4; tannin 2: 60 °C / mit Oxalsaeure, ZnCl2 oder besser P2O5 View Scheme

EDMA (97-90-5) → allyl methacrylate (96-05-9)

2-methylpropenal (78-85-3) + allyl alcohol (107-18-6) → allyl methacrylate (96-05-9)

Conditions	Yield
Stage #1: 2-methylpropenal With tert-butylhypochlorite In tetrachloromethane at 20 - 50℃; for 5.5 - 6.5h; Stage #2: allyl alcohol In tetrachloromethane at 0 - 20℃; for 15.5h;

allyl dodecanoate (7003-75-0) + methyl methacrylate (97-63-2) → allyl methacrylate (96-05-9) + ethyl laurate (106-33-2)

Conditions	Yield
With 15percent (w/w) Candida antarctica lipase B immobilised onto macroporous acrylic resin at 50℃; for 1h; Enzymatic reaction;	A 34.2 %Chromat. B n/a

2-bromo-2-methylpropionic acid (2052-01-9) + allyl methacrylate (96-05-9) + methacrylic acid methyl ester (80-62-6) → Poly(methyl methacrylate-b-allyl methacrylate) end-capped with isobutyric acid, block copolymerization, Mn 6800, Mw/Mn 1.21

Conditions	Yield
Multistep reaction.;	100%

Triethoxysilane (998-30-1) + allyl methacrylate (96-05-9) → 3-methacryloyloxypropyltriethoxysilane (21142-29-0)

Conditions	Yield
With platinum-containing olefin organic polymer catalyst at 25℃; for 24h;	98%
With dihydrogen hexachloroplatinate; Triethoxyvinylsilane; isopropyl alcohol In pentane at 50℃; for 1.5h; Product distribution; Mechanism; influence unsaturated Si-comp. on rate of hydrosilylation; effect of different solvents; further functionalized alkenes;	66 % Chromat.
Stage #1: Triethoxysilane; allyl methacrylate With dihydrogen hexachloroplatinate; tetramethyldivinyldisiloxane; N,N'-diphenyl-1,4-phenylenediamine; triphenylphosphine In isopropyl alcohol at 95 - 135℃; for 2.25h; Stage #2: With dmap In isopropyl alcohol

allyl methacrylate (96-05-9) + platinum (7440-06-4) → γ-methacryloxypropyltrichlorosilane

Conditions	Yield
With trichlorosilane; [SG]-S-Pt In hexane	98%

dimethylmonochlorosilane (1066-35-9) + allyl methacrylate (96-05-9) → 3-Methacryloxypropyldimethylchlorosilane (24636-31-5)

Conditions	Yield
Stage #1: dimethylmonochlorosilane; allyl methacrylate With 10H-phenothiazine; platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex In 5,5-dimethyl-1,3-cyclohexadiene at 80℃; under 5171.62 Torr; for 0.666667h; Flow reactor; Sealed tube; Inert atmosphere; Stage #2: With 2,6-di-tert-butyl-4-methyl-phenol In 5,5-dimethyl-1,3-cyclohexadiene at 80℃; for 1h; Temperature; Inert atmosphere;	97.9%
With platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex In toluene at 70℃; for 3h;	96%
With dihydrogen hexachloroplatinate; 10H-phenothiazine In tetrahydrofuran at 80℃; for 0.5h;	72%
With N,N-dimethyl-(3,5-di-tert-butyl-4-hydroxybenzyl)ammonium chloride; Platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex at 65 - 80℃; for 1h;

Dichloromethylsilane (75-54-7) + allyl methacrylate (96-05-9) → 3-(dichloromethylsilyl)propyl methacrylate (18301-56-9)

Conditions	Yield
With platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex In toluene at 70℃; for 3h;	97%
With dihydrogen hexachloroplatinate; 10H-phenothiazine In tetrahydrofuran at 80℃; for 0.5h;	83%
With dihydrogen hexachloroplatinate; 2-Ethylhexyl alcohol; 2,6-di-tert-butyl-4-methyl-phenol; platinum In toluene at 70 - 80℃; for 4h;

allyl methacrylate (96-05-9) + C22H44F12O4Si5 → C29H54F12O6Si5

Conditions	Yield
With complex of alkali-neutralized chloroplatinic acid with vinyl siloxane, containing 0.5percent of platinum In methyl cyclohexane; toluene at 70 - 100℃; for 2h;	97%

allyl methacrylate (96-05-9) + trichlorosilane (10025-78-2) → 3-(trichlorosilyl)propyl 2-methylprop-2-enoate (7351-61-3)

Conditions	Yield
With platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex In toluene at 70℃; for 3h;	96%

allyl methacrylate (96-05-9) + C20H62O9Si10 (1293367-37-9) → C34H82O13Si10

Conditions	Yield
platinum 1,3-divinyl-1,1,3,3-tetramethyldisiloxane In toluene; xylene at 20℃; Inert atmosphere;	95.8%

allyl methacrylate (96-05-9) + methacrylic acid methyl ester (80-62-6) → poly(methyl methacrylate-allyl methacrylate) copolymer, MMA/AMA=30, Mn=38400

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In toluene at 80℃; for 8h; radical copolymerization;	95.6%

triethylsilane (617-86-7) + allyl methacrylate (96-05-9) → triethylsilyl 2,2-dimethyl-4-pentenoate

Conditions	Yield
With 1,3,5-trimethyl-2,4,6-tris-(3,5-di-tert-butyl-4-hydroxybenzyl)benzene; tris(pentafluorophenyl)borate In toluene at 40 - 50℃; for 3.3h;	95.6%

1,1,3,3-Tetramethyldisiloxane (3277-26-7) + allyl methacrylate (96-05-9) → 1,3-bis(2,2-dimethyl-4-pentenoyloxy)-1,1,3,3-tetramethyldisiloxane

Conditions	Yield
With 1,3,5-trimethyl-2,4,6-tris-(3,5-di-tert-butyl-4-hydroxybenzyl)benzene; tris(pentafluorophenyl)borate In toluene at 1.5 - 12℃; for 12h;	94.8%

trimethoxysilane (2487-90-3) + allyl methacrylate (96-05-9) → [3-(methacryloyloxy)propyl]trimethoxysilane (2530-85-0)

Conditions	Yield
With dihydrogen hexachloroplatinate; 10H-phenothiazine at 85℃; under 1125.11 - 3000.3 Torr; for 4h; Catalytic behavior; Pressure; Autoclave; Inert atmosphere;	94.3%
With 4-aminotriphenylamine; 2,6-di-tert-butyl-4-methyl-phenol; acetone; dihydrogen hexachloroplatinate(IV) hexahydrate at 75℃; under 18751.9 Torr; Inert atmosphere;
With dihydrogen hexachloroplatinate(IV) hexahydrate In acetylacetone at 105℃;

oct-1-ene (111-66-0) + allyl methacrylate (96-05-9) + octakis(dimethylsiloxy)octasilsesquioxane → C76H160O28Si16

Conditions	Yield
Stage #1: oct-1-ene; octakis(dimethylsiloxy)octasilsesquioxane With bis(1,5-cyclooctadiene)diiridium(I) dichloride; Karstedt's catalyst In toluene at 90℃; Stage #2: allyl methacrylate In toluene at 60℃;	94%

allyl methacrylate (96-05-9) + para-thiocresol (106-45-6) → allyl 2-hydroxy-2-methyl-3-(p-tolylthio)propanoate

Conditions	Yield
Stage #1: allyl methacrylate; para-thiocresol In 1,2-dichloro-ethane; acetonitrile at 20℃; for 2.3h; Stage #2: With triphenylphosphine In 1,2-dichloro-ethane; acetonitrile for 2h;	93%
With oxygen; copper diacetate; 4-methoxybenzoic acid In 1,2-dichloro-ethane at 50℃; for 3h;	88%

styrene (292638-84-7) + allyl methacrylate (96-05-9) → poly(styrene-allyl methacrylate) copolymer, St/AMA=68.4, Mn=40200

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In toluene at 80℃; for 8h; radical copolymerization;	92.3%

allyl methacrylate (96-05-9) + methacrylic acid methyl ester (80-62-6) → poly(methyl methacrylate-allyl methacrylate) copolymer, MMA/AMA=15, Mn=56100

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In toluene at 80℃; for 8h; radical copolymerization;	92.3%

allyl methacrylate (96-05-9) + methacrylic acid methyl ester (80-62-6) → poly(methyl methacrylate-allyl methacrylate) copolymer, MMA/AMA=50, Mn=49800

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In toluene at 80℃; for 8h; radical copolymerization;	91.8%

allyl methacrylate (96-05-9) + diethyl 8-oxo-8H-cyclopenta-(a)-acenaphthylene-7,9-dicarboxylate (57830-24-7) → 8-Methyl-8,9-dihydro-fluoranthene-7,8,10-tricarboxylic acid 8-allyl ester 7,10-diethyl ester

Conditions	Yield
In chloroform for 4h; Heating;	91%

allyl methacrylate (96-05-9) → 3-methyl-5H-furan-2-one (22122-36-7)

Conditions	Yield
With C28H32Cl2N2ORu In toluene at 70℃; for 18h; Inert atmosphere;	91%

styrene (292638-84-7) + allyl methacrylate (96-05-9) → poly(styrene-allyl methacrylate) copolymer, St/AMA=7.3, Mn=37000

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In toluene at 80℃; for 8h; radical copolymerization;	90.7%

allyl methacrylate (96-05-9) + dicyclopentadiene → 2-methyl-acrylic acid 3-(3-vinyl-1,2,3,3a,4,6a-hexahydro-pentalen-1-yl)-allyl ester

Conditions	Yield
Grubbs catalyst first generation In dichloromethane at 20℃; for 2h;	90%

allyl methacrylate (96-05-9) + Triethoxyvinylsilane (78-08-0) + octakis(dimethylsiloxy)octasilsesquioxane → C76H168O40Si20

Conditions	Yield
Stage #1: Triethoxyvinylsilane; octakis(dimethylsiloxy)octasilsesquioxane With bis(1,5-cyclooctadiene)diiridium(I) dichloride; Karstedt's catalyst In toluene at 90℃; Stage #2: allyl methacrylate In toluene at 60℃;	90%

styrene (292638-84-7) + allyl methacrylate (96-05-9) → poly(styrene-allyl methacrylate) copolymer, St/AMA=45.5, Mn=38500

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In toluene at 80℃; for 8h; radical copolymerization;	89.1%

styrene (292638-84-7) + allyl methacrylate (96-05-9) → poly(styrene-allyl methacrylate) copolymer, St/AMA=15.0, Mn=30400

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In toluene at 80℃; for 8h; radical copolymerization;	88.4%

allyl methacrylate (96-05-9) → 3-(trichlorosilyl)propyl 2-methylprop-2-enoate (7351-61-3)

Conditions	Yield
With dihydrogen hexachloroplatinate; 10H-phenothiazine; trichlorosilane In tetrahydrofuran at 80℃; for 0.5h;	88%
With dihydrogen hexachloroplatinate; Triethoxyvinylsilane; trichlorosilane at 50 - 80℃; for 2.5h;

allyl methacrylate (96-05-9) + Benzoylformic acid (611-73-4) → C14H16O3

Conditions	Yield
With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; potassium tert-butylate In acetonitrile at 20℃; Inert atmosphere; Sealed tube; Irradiation;	88%

allyl methacrylate (96-05-9) + diethyltin dihydride (871-33-0) → Diethyl-bis-<2-allyloxycarbonyl-propyl>-stannan (22403-05-0)

Conditions	Yield
In neat (no solvent) closed tube, 90-100°C, 1h, N2;;	86.8%
In not given reaction in a bomb tube at 90-100°C for 1 h;;

allyl methacrylate (96-05-9) + methacrylic acid methyl ester (80-62-6) → poly(methyl methacrylate-allyl methacrylate) copolymer, MMA/AMA=5.8, Mn=43300

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In toluene at 80℃; for 8h; radical copolymerization;	86%

Upstream product

• 408318-09-2 α-acetoxy-isobutyric acid allyl ester 
• 7003-75-0 allyl dodecanoate 
• 97-63-2 methyl methacrylate 
• 1393670-68-2 allyl 2-((tert-butyl(1-(diethoxyphosphoryl)-2,2-dimethylpropyl)amino)oxy)-2-methylpropanoate 
• 78-85-3 2-methylpropenal 
• 107-18-6 allyl alcohol 
• 97-90-5 EDMA 
• 17859-93-7 2-allyloxy-2-methylpropanoic acid 
• 106-91-2 2,3-Epoxypropyl methacrylate 
• 79-41-4 poly(methacrylic acid) 
• 591-87-7 Allyl acetate 
• 874487-06-6 α-allyloxy-isobutyric acid allyl ester 
• 19444-21-4 allyl 2-hydroxyisobutyrate 
• 80-62-6 methacrylic acid methyl ester 

Downstream Products

• 18151-85-4 <1-(2-methylpropenoyloxy)propyl>pentamethyldisiloxane 
• 129111-02-0 2-Iodo-3-p-toluenesulphonylpropyl methacrylate 
• 129111-03-1 Allyl 2-iodo-2-methyl-3-p-toluenesulphonylpropanoate 
• 7351-61-3 3-(trichlorosilyl)propyl 2-methylprop-2-enoate 
• 106-91-2 2,3-Epoxypropyl methacrylate 
• 140914-83-6 2-Methyl-oxirane-2-carboxylic acid allyl ester 
• 300-57-2 allylbenzene 
• 124-11-8 non-1-ene 
• 2530-85-0 [3-(methacryloyloxy)propyl]trimethoxysilane 
• 18547-93-8 1,3-bis<3-(2-methylpropenoyloxy)propyl>tetramethyldisiloxane 
• 1333-74-0 hydrogen 

Relevant articles and documents

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Solvent-free biocatalytic interesterification of acrylate derivatives

The ability of diverse commercial lipases and whole cells (fungal resting cells) to synthesise allyl and dichloropropyl acrylate from allyl dodecanoate through an interesterification process is presented. The process was carried out without solvent in a conventional batch system. The best biocatalyst among those studied was the commercial enzyme CALB (Candida antarctica lipase B immobilised onto a macroporous acrylic resin). The reaction was sensitive to water activity, and a decrease in the yield was observed at the highest activity studied. CALB could also be applied to diverse acrylic derivatives, although the yields decreased using either ethyl methacrylate or acrylic acid.

Rhenium-catalyzed allylation of C-H bonds of benzoic and acrylic acids

We have succeeded in the allylation of aromatic and olefinic C-H bonds of benzoic and acrylic acids using a rhenium catalyst, Re2(CO) 10. In this reaction, isomerization of the introduced allyl group to the 1-propenyl group did not occur.