4245-37-8

Usage

Uses

Used in Coatings Industry:
Vinyl Methacrylate is used as a monomer in the production of polymers and co-polymers for coatings. It contributes to the formation of durable and weather-resistant coatings that are widely used in various applications, such as automotive, architectural, and industrial coatings.
Used in Adhesives Industry:
In the adhesives industry, Vinyl Methacrylate is used as a component in the formulation of adhesives. Its properties allow for the creation of strong bonds between different materials, making it a valuable ingredient in the production of various types of adhesives.
Used in Sealants Industry:
Vinyl Methacrylate is used as a key ingredient in the formulation of sealants. Its ability to form strong, flexible, and durable bonds makes it an essential component in the production of sealants for construction and other industries.
Used in Oil Additives Industry:
In the oil additives industry, Vinyl Methacrylate is used to enhance the performance of lubricants and other oil-based products. Its incorporation into these products can improve their viscosity, stability, and overall performance.
Used in Textiles Industry:
Vinyl Methacrylate is used in the textiles industry as a component in the production of various types of fibers and fabrics. Its properties contribute to the creation of textiles with improved strength, durability, and resistance to wear and tear.

InChI:InChI=1/C6H8O2/c1-4-8-6(7)5(2)3/h4H,1-2H2,3H3

Synthetic route

vinyl acetate (108-05-4) + poly(methacrylic acid) (79-41-4) → vinyl methacrylate (4245-37-8)

Conditions	Yield
With sulfuric acid; mercury(II) diacetate

poly(methacrylic acid) (79-41-4) + acetic anhydride (108-24-7) + acetylene (74-86-2) → vinyl methacrylate (4245-37-8) + 1,1-bis-methacryloyloxy-ethane (25073-88-5)

Conditions	Yield
With mercury(II) orthophosphate

octanol (111-87-5) + vinyl methacrylate (4245-37-8) → n-octyl methacrylate (2157-01-9)

Conditions	Yield
With Cp*2Sm(THF)2 In toluene Ambient temperature; further reagent: SmI2;	99%

oxacyclotridecan-2-one (947-05-7) + vinyl methacrylate (4245-37-8) → poly(12-dodecanolide), terminal-methacrylated, Mn 3700, functionality 0.57

Conditions	Yield
pseudomonas fluorescens lipase at 60℃; for 72h; Polymerization; acylation;	98%

4-Hydroxy-dihydro-furan-2-on (5469-16-9, 7331-52-4, 58081-05-3, 131432-37-6) + vinyl methacrylate (4245-37-8) → β-methacryloyloxy-γ-butyrolactone (130224-95-2)

Conditions	Yield
With Novozym 435 In (E)-2-methyl-2-butenoate at 50℃; for 24h; Conversion of starting material;	98%
With Lipase P In tert-butyl alcohol at 30℃; for 24h; Conversion of starting material;	84.53%
With Lipase PL In tert-butyl alcohol at 30℃; for 24h; Conversion of starting material;	61.32%

vinyl methacrylate (4245-37-8) + bis(pinacol)diborane (73183-34-3) → vinyl 2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate (1454308-51-0)

Conditions	Yield
Stage #1: bis(pinacol)diborane With copper(II) carbonate; triphenylphosphine In water at 20℃; for 0.5h; Inert atmosphere; Stage #2: vinyl methacrylate In water at 30℃; for 20h; Inert atmosphere;	94%
Stage #1: bis(pinacol)diborane With copper carbonate hydroxide; triphenylphosphine In water at 20℃; for 0.5h; Inert atmosphere; Stage #2: vinyl methacrylate In water at 30℃; for 20h; Inert atmosphere;	94%
Stage #1: bis(pinacol)diborane With copper(II) carbonate; triphenylphosphine In water at 20℃; for 0.833333h; Inert atmosphere; Stage #2: vinyl methacrylate In water at 30℃; for 20h;	94%
Stage #1: bis(pinacol)diborane With copper(II) carbonate; triphenylphosphine In water at 20℃; for 0.5h; Inert atmosphere; Stage #2: vinyl methacrylate In water at 30℃; for 20h; Inert atmosphere;	94%

vinyl methacrylate (4245-37-8) + Isosorbide (652-67-5) → D-isosorbide 5-methacrylate

Conditions	Yield
With Rhizomucor miehei lipase Enzymatic reaction; regioselective reaction;	93%
With Lipozyme RM IM In tert-butyl methyl ether at 20℃; for 60h; Enzymatic reaction;	87.3%

oxacyclotridecan-2-one (947-05-7) + vinyl methacrylate (4245-37-8) → poly(12-dodecanolide), terminal-methacrylated, Mn 3600, functionality 0.83

Conditions	Yield
pseudomonas fluorescens lipase at 60℃; for 72h; Polymerization; acylation;	92%

1-Bromo-11-hydroxyundecane (1611-56-9) + vinyl methacrylate (4245-37-8) → 2-methylacrylic acid 11-bromoundecyl ester (33795-49-2)

Conditions	Yield
1,3-dicyclohexyl-imidazol-2-ylidene In tetrahydrofuran at 20℃; for 0.25h;	90%

vinyl methacrylate (4245-37-8) + p-hydroxyphenethyl 17-L-[(2'-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenamide → p-hydroxyphenethyl 17-L-[(2'-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenamide-6',6"-dimethacrylate

Conditions	Yield
With Novozym 435 In tetrahydrofuran at 50℃; for 80h;	90%

p-hydroxyphenethyl 17-L-[(2'-O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy]-cis-9-octadecenamide (585542-26-3) + vinyl methacrylate (4245-37-8) → p-hydroxyphenethyl 17-L-[(2'-O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy]-cis-9-octadecenamide 6',6''-dimethacrylate (585542-32-1)

Conditions	Yield
novozyme 435 In tetrahydrofuran at 50℃; for 80h; Product distribution / selectivity; Enzymatic reaction;	90%

vinyl methacrylate (4245-37-8) + 2-methyladamantan-2-ol (702-98-7) → vinyl 2-methyl-3-(2-methyladamantan-2-yl)propanoate

Conditions	Yield
With cyclopentadienyl titanium(IV) trichloride; triethylsilyl chloride; zinc In tetrahydrofuran at 60℃; for 12h; Molecular sieve; Sealed tube; Inert atmosphere;	89%

vinyl methacrylate (4245-37-8) + p-hydroxyphenethyl 17-L-[(2'-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenamide → p-hydroxyphenethyl 17-L-[(2'-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenamide-6"-methacrylate

Conditions	Yield
With Lipase PS-C In tetrahydrofuran at 40℃; for 72h;	88%

ethyl 17-L-[(2'-O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy]-cis-9-octadecenoate (220608-02-6) + vinyl methacrylate (4245-37-8) → p-hydroxyphenethyl 17-L-[(2'-O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy]-cis-9-octadecenamide 6',6''-dimethacrylate (585542-32-1)

Conditions	Yield
Stage #1: tyrosamine; ethyl 17-L-[(2'-O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy]-cis-9-octadecenoate; novozyme 435 In tetrahydrofuran at 50℃; for 24h; Enzymatic reaction; Stage #2: vinyl methacrylate In tetrahydrofuran at 50℃; for 80h; Product distribution / selectivity; Enzymatic reaction;	88%

p-hydroxyphenethyl 17-L-[(2'-O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy]-cis-9-octadecenamide (585542-26-3) + vinyl methacrylate (4245-37-8) → ethyl 17-L-[(2'-O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy]-cis-9-octadecenamide 6"-methacrylate (585542-36-5)

Conditions	Yield
Lipase PS-C In tetrahydrofuran at 40℃; for 72h; Product distribution / selectivity; Enzymatic reaction;	88%

vinyl methacrylate (4245-37-8) + (Z)-17-[(2R,3R,4S,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-3-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-octadec-9-enoic acid ethyl ester → ethyl 17-L-[(2'-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate-6"-acetate

Conditions	Yield
With Lipase PS-C In tetrahydrofuran at 40℃; for 72h;	86%

ethyl 17-L-[(2'-O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy]-cis-9-octadecenoate (220608-02-6) + vinyl methacrylate (4245-37-8) → ethyl 17-L-[(2'-O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy]-cis-9-octadecenoate 6"-methacrylate (585542-25-2)

Conditions	Yield
Lipase PS-C In tetrahydrofuran at 40℃; for 72h; Product distribution / selectivity; Enzymatic reaction;	86%

vinyl methacrylate (4245-37-8) + 17-L-([2'-O-β-D-glucopyranosyl-β-D-glucopyranosyl]oxy)-9-octadecenoic acid 1'-4"-lactone 6"-acetate → 17-L-([2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl]oxy)-9-octadecenoic acid 1′-4″-lactone 6′-methacrylate 6″-acetate

Conditions	Yield
With amano lipase PS immobilized on diatomaceous earth In tetrahydrofuran at 45℃; for 8h; Inert atmosphere; Enzymatic reaction; regioselective reaction;	85%

vinyl methacrylate (4245-37-8) → glycidyl mathacrylate (48106-38-3)

Conditions	Yield
With nickel-doped graphene carbon nitride nanoparticles; air In acetonitrile at 25℃; for 8h; Irradiation; Green chemistry;	85%

triethylsilane (617-86-7) + vinyl methacrylate (4245-37-8) → 2-methyl-1-triethylsiloxy-1-vinyloxypropene

Conditions	Yield
Stage #1: triethylsilane With 1,3,5-trimethyl-2,4,6-tris-(3,5-di-tert-butyl-4-hydroxybenzyl)benzene; tris(pentafluorophenyl)borate at 20℃; for 0.5h; Neat (no solvent); Stage #2: vinyl methacrylate at 1.5 - 20℃; for 9.5h; Neat (no solvent); Cooling with ice water;	84.5%

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%

vinyl methacrylate (4245-37-8) + 10-(4-(5-(9,9-dihexyl-7-(5'-(pyridin-4-yl)-2,2'-bithiophen-5-yl)-9H-fluoren-2-yl)thiophen-2-yl)phenoxy)decan-1-ol (1263559-53-0) → 10-(4-(5-(9,9-dihexyl-7-(5'-(pyridin-4-yl)-2,2'-bithiophen-5-yl)-9H-fluoren-2-yl)thiophen-2-yl)phenoxy)decyl methacrylate (1263559-56-3)

Conditions	Yield
With 2,6-di-tert-butyl-4-methyl-phenol; 1,3-dichlorotetrabutyldistannoxane In tetrahydrofuran at 50℃; for 48h; Inert atmosphere;	81%

vinyl methacrylate (4245-37-8) + p-hydroxyphenethyl 17-L-[(2'-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenamide → p-hydroxyphenethyl 17-L-[(2'-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenamide-6'-methacrylate + p-hydroxyphenethyl 17-L-[(2'-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenamide-6',6"-dimethacrylate

Conditions	Yield
With Novozym 435 In tetrahydrofuran at 40℃; for 20h;	A 80% B 6%

p-hydroxyphenethyl 17-L-[(2'-O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy]-cis-9-octadecenamide (585542-26-3) + vinyl methacrylate (4245-37-8)

Conditions	Yield
novozyme 435 In tetrahydrofuran at 40℃; for 20h; Product distribution / selectivity; Enzymatic reaction;	A 80% B 6%

oxacyclotridecan-2-one (947-05-7) + vinyl methacrylate (4245-37-8)

Conditions	Yield
pseudomonas fluorescens lipase at 60℃; for 72h; Polymerization; acylation;	79%

vinyl methacrylate (4245-37-8) + 5-Fluoro-2'-deoxyuridine (50-91-9) → 3'-O-methacryloyl-FUdR (1118767-26-2) + 5'-O-methacryloyl-FUdR (1118767-45-5) + 3',5'-di-O-methacryloyl-FUdR (96100-06-0)

Conditions	Yield
With PSL-C; 1-n-butyl-2,3-dimethylimidazolium hexafluorophosphate In tetrahydrofuran at 40℃; for 23h; regioselective reaction;	A 77% B n/a C n/a

vinyl methacrylate (4245-37-8) + C56H84O4Sc + triethylphosphine (554-70-1) → C54H86O5PSc

Conditions	Yield
In toluene at 20℃; for 1h; Reagent/catalyst; Inert atmosphere; Schlenk technique; Glovebox;	77%

vinyl methacrylate (4245-37-8) + (-)-trans-sobrerol (71697-84-2) → trans-sobreryl methacrylate

Conditions	Yield
With Amano lipase from Pseudomonas fluorescens at 80℃; for 72h; Temperature; Darkness;	76%

vinyl methacrylate (4245-37-8)

Conditions	Yield
With Novozym 435 In acetonitrile at 50℃; for 120h; Enzymatic reaction;	70%
With Novozym 435 In acetonitrile at 50℃; for 120h;	60%
With Novozym 435; 2,6-di-tert-butyl-4-methyl-phenol In acetonitrile at 50℃; for 120h;

Upstream product

• 108-05-4 vinyl acetate 
• 79-41-4 poly(methacrylic acid) 
• 108-24-7 acetic anhydride 
• 74-86-2 acetylene 
• 75-07-0 acetaldehyde 
• 920-46-7 Methacryloyl chloride 
• 760-93-0 methacryloyl anhydride 

Downstream Products

• 33795-49-2 11-bromoundecyl methacrylate 
• 1145787-55-8 3-(6-benzylamino-purin-9-yl)-2-methyl-propionic acid vinyl ester 
• 1445-91-6 (S)-1-phenylethanol 
• 17199-94-9 (R)-α-methylbenzyl methacrylate 
• 46810-73-5 6-O-glucosyl methacrylate 
• 75-07-0 acetaldehyde 
• 2210-28-8 propyl methacrylate 
• 2998-18-7 1-methylpropyl methacrylate 
• 13818-44-5 (2-oxo-1,3-dioxolane-4-yl)methyl methacrylate 
• 106-91-2 2,3-Epoxypropyl methacrylate 

Relevant academic research and scientific papers

Process for Preparing Vinyl Carboxylates

The present invention relates to a process for preparing vinyl carboxylates, wherein a carboxylic acid is reacted with an alkyne compound in the presence of a catalyst which is selected from carbonyl complexes, halides and oxides of rhenium, of manganese, of tungsten, of molybdenum, of chromium and of iron and rhenium metal at a temperature of ≦300° C. The process gives the desired vinyl esters with high yield.

Transvinylation process for the preparation of thermally labile vinyl compounds and for vinyl compounds prepared from thermally labile acids

A process for the transvinylation of a vinyl derivative of a Bronsted acid with a different Bronsted acid which comprises providing a liquid phase mixture containing said vinyl derivative and said Bronsted acid in the presence of a ruthenium compound at a temperature at which transvinylation occurs and recovering as a product of transvinylation the vinyl derivative of the different Bronsted acid. The process is most favorably employed using carboxylic acids to make vinyl esters of carboxylic acids.