2177-18-6

Basic information

• Product Name: VINYL ACRYLATE
• Synonyms: VINYL ACRYLATE;2-propenoicacid,ethenylester;Acrylic acid, vinyl ester;acrylicacid,vinylester;ethenyl2-propenoate;VINYL ACRYLATE 98%;Vinyl acrylate, stabilized, 98+%;3-Oxahexa-1,5-diene-4-one
• CAS NO: 2177-18-6
• Molecular Formula: C₅H₆O₂
• Molecular Weight: 98.1
• EINECS: 218-538-1
• Product Categories: monomer
• Mol File: 2177-18-6.mol
• Article Data: 6

Chemical Properties

• Melting Point: -81.9°C
• Boiling Point: 90-92 °C(lit.)
• Flash Point: 36 °F
• Appearance: /
• Density: 0.942 g/mL at 25 °C(lit.)
• Vapor Pressure: 53.7mmHg at 25°C
• Refractive Index: n20/D 1.432(lit.)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: VINYL ACRYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: VINYL ACRYLATE(2177-18-6)
• EPA Substance Registry System: VINYL ACRYLATE(2177-18-6)

Safety Data

• Hazard Codes: F,T,T+
• Statements: 11-25-34-41-38-28-20
• Safety Statements: 9-16-26-28-36/37/39-45
• RIDADR: UN 3286 3/PG 2
• WGK Germany: 3
• RTECS: UD3341000
• Hazardous Substances Data: 2177-18-6(Hazardous Substances Data)

Usage

Uses

This acrylate monomer has a vinyl group for functionalization. It can also be used as a crosslinkable monomer.

Hazard

A poison by ingestion. Low toxicity by inhalation. A severe skin and eye irritant.

InChI:InChI=1/C5H6O2/c1-3-5(6)7-4-2/h3-4H,1-2H2

Synthetic route

vinyl β-chloropropionate (5309-67-1) → vinyl acrylate (2177-18-6)

Conditions	Yield
With sodium methylate In methanol at 50 - 55℃;	98%

vinyl acetate (108-05-4) + acrylic acid (79-10-7) → vinyl acrylate (2177-18-6)

Conditions	Yield
With boron trifluoride diethyl etherate; hydroquinone
With rhodium(III) chloride trihydrate; sodium formate at 80℃; for 24h;	67 %Chromat.

divinylmercury (1119-20-6) + acrylic acid (79-10-7) → vinyl acrylate (2177-18-6)

Conditions	Yield
In n-heptane for 0.5h; Heating;

ethene (74-85-1) + acrylic acid (79-10-7) → α-methylene-γ-butyrolactone (547-65-9) + vinyl acrylate (2177-18-6)

Conditions	Yield
With oxygen; sodium 2-propenoate; p-benzoquinone; palladium diacetate In 1-methyl-pyrrolidin-2-one at 50 - 60℃; under 1838.93 - 2942.29 Torr; for 4 - 36h; Product distribution / selectivity;	A 5.7 - 65 %Chromat. B 4.8 - 18 %Chromat.
palladium diacetate In 2-n-butyl-4-(hydroxymethyl)imidazole at 50℃; under 367.786 Torr; for 16h; Product distribution / selectivity;	A 0.5 %Chromat. B 1.3 %Chromat.
With 4-methoxy-phenol; p-benzoquinone; palladium 10% on activated carbon at 80℃; under 2574.5 Torr; for 16h; Product distribution / selectivity;	A 6.0 %Chromat. B 11.8 %Chromat.

acrylic acid (79-10-7) → vinyl acrylate (2177-18-6)

acrylic acid (79-10-7) + acetylene (74-86-2) → vinyl acrylate (2177-18-6)

Conditions	Yield
decacarbonyldirhenium(0) In toluene at 140℃; under 15001.5 Torr; for 17h; Product distribution / selectivity;

octanol (111-87-5) + vinyl acrylate (2177-18-6) → octyl acrylate (2499-59-4)

Conditions	Yield
With Cp*2Sm(THF)2 In toluene Ambient temperature; further reagent: SmI2;	99%
With 1,3-dichlorotetrabutyldistannoxane at 50℃; for 15h;	98%
With 1,3-dichlorotetrabutyldistannoxane at 50℃; for 15h;	98%
In 2,2,4-trimethylpentane at 37℃; immobilized lipase from Candida cylindracea;

samarium diiodide + vinyl acrylate (2177-18-6) + 1-adamanthanol (768-95-6) → adamantane monoacrylate

Conditions	Yield
In 1,4-dioxane	99%

hexane-1,5-diol (928-40-5) + vinyl acrylate (2177-18-6) → 1-acryloyloxy-5-hydroxyhexane

Conditions	Yield
With 1,3-dichlorotetrabutyldistannoxane at 30℃; for 45h;	96%
With 1,3-dichlorotetrabutyldistannoxane at 30℃; for 45h;	96%

p-hydroxyphenethyl alcohol (501-94-0) + vinyl acrylate (2177-18-6) → 2-(4-hydroxyphenyl)ethyl prop-2-enoate

Conditions	Yield
With 1,3-dichlorotetrabutyldistannoxane In acetonitrile at 50℃; for 36h;	96%

vinyl acrylate (2177-18-6) + 1H-4(5)-nitroimidazole (3034-38-6) → 3-(4-nitroimidazol-1-yl)-propionic acid vinyl ester

Conditions	Yield
With 1-butyl-3-methylimidazolium hydroxide at 25℃; for 0.5h; Michael addition;	96%
With acylase Amano from Aspergillus oryzae In dimethyl sulfoxide at 50℃; for 0.5h; Michael addition reaction;	85%

5-fluorouracil (51-21-8) + vinyl acrylate (2177-18-6) → 3-(5-fluorouracil-1-yl)propionic acid vinyl ester (884308-97-8)

Conditions	Yield
With D-aminoacylase from Escherichia coli In dimethyl sulfoxide at 25℃; for 0.416667h; Michael addition; Enzymatic reaction; regioselective reaction;	96%

vinyl acrylate (2177-18-6) + uracil (66-22-8) → 3-(uracil-1-yl)propionic acid vinyl ester (884308-95-6)

Conditions	Yield
With D-aminoacylase from Escherichia coli In dimethyl sulfoxide at 25℃; for 1h; Michael addition; Enzymatic reaction; regioselective reaction;	96%

vinyl acrylate (2177-18-6) + benzyl alcohol (100-51-6) → benzylacrylate (2495-35-4)

Conditions	Yield
With N,N'-bismesityl-imidazol-2-ylidene In tetrahydrofuran at 20℃; for 0.25h;	95%
With 4 A molecular sieve; 1,3-dicyclohexyl-imidazol-2-ylidene In tetrahydrofuran at 20℃; for 0.25h;	95%
With hexamethyltriamido-N-benzylimidophosphate In tetrahydrofuran at 20℃; for 24h; Acylation;	87%
In 2,2,4-trimethylpentane at 37℃; immobilized lipase from Candida cylindracea;

5-bromouracil (51-20-7) + vinyl acrylate (2177-18-6) → 3-(5-bromouracil-1-yl)propionic acid vinyl ester (1217794-07-4)

Conditions	Yield
With D-aminoacylase from Escherichia coli In dimethyl sulfoxide at 25℃; for 0.416667h; Michael addition; Enzymatic reaction; regioselective reaction;	95%

vinyl acrylate (2177-18-6) + thymin (65-71-4) → 3-(thymin-1-yl)propionic acid vinyl ester (884308-96-7)

Conditions	Yield
With D-aminoacylase from Escherichia coli In dimethyl sulfoxide at 25℃; for 1h; Michael addition; Enzymatic reaction; regioselective reaction;	94%

vinyl acrylate (2177-18-6) + diethylamine (109-89-7) → vinyl β-diethylaminopropionate (84115-01-5)

Conditions	Yield
at 50 - 55℃; for 0.5h;	90%

vinyl acrylate (2177-18-6) + methyl 17-L-(<2'-O-β-D-glucopyranosyl-β-D-glucopyranosyl>-oxy)-cis-9-octadecenoate → methyl 17-L-(<2'-O-β-D-glucopyranosyl-β-D-glucopyranosyl>-oxy)-cis-9-octadecenoate 6',6''-diacrylate

Conditions	Yield
In tetrahydrofuran at 35℃; for 96h; lipase Novozym 435 from Candida antarctica;	87%

vinyl acrylate (2177-18-6) + methyl (-)-quinate (191916-39-9) → methyl 4-O-acryloylquinate

Conditions	Yield
With Candida antarctica Lipase A; 4 A molecular sieve In various solvent(s) at 40℃; for 7h;	87%

vinyl acrylate (2177-18-6) + methyl 17-L-([2-O-β-D-glucopyranosyl-β-D-glucopyranosyl]-oxy)-cis-9-octadecenoate (213754-46-2) → methyl 17-L-([2'-O-β-D-glucopyranosyl-β-D-glucopyranosyl]oxy)-cis-9-octadecenoate 6',6"-diacrylate (220608-05-9)

Conditions	Yield
novozyme 435 In tetrahydrofuran at 35℃; for 96h; Product distribution / selectivity; Enzymatic reaction;	87%

piperidine (110-89-4) + vinyl acrylate (2177-18-6) → vinyl β-piperidinopropionate (84115-02-6)

Conditions	Yield
at 50℃; for 0.5h;	85%

vinyl acrylate (2177-18-6) + diethyl 8-oxo-8H-cyclopenta-(a)-acenaphthylene-7,9-dicarboxylate (57830-24-7) → 8,9-Dihydro-fluoranthene-7,8,10-tricarboxylic acid 7,10-diethyl ester 8-vinyl ester

Conditions	Yield
In chloroform for 0.7h; Heating;	84%

vinyl acrylate (2177-18-6) → vinyl β-chloropropionate (5309-67-1)

Conditions	Yield
With hydrogenchloride In diethyl ether at -70 - -60℃; for 2.5h;	83%

vinyl acrylate (2177-18-6) + 17-L-(<2'-O-β-D-glucopyranosyl-β-D-glucopyranosyl>-oxy)-cis-9-octadecenoic acid 1',6''-lactone → 17-L-(<2'-O-β-D-glucopyranosyl-β-D-glucopyranosyl>-oxy)-cis-9-octadecenoic acid 1',6''-lactone 6'-acrylate

Conditions	Yield
With zeolite In tetrahydrofuran at 35℃; for 96h; lipase Novozym 435 from Candida antarctica;	83%

17-L-([2'-O-β-D-glucopyranosyl-β-D-glucopyranosyl]oxy)-cis-9-octadecenoic acid 1',6"-lactone (213754-48-4) + vinyl acrylate (2177-18-6) → 17-L-([2'-O-β-D-glucopyranosyl-β-D-glucopyranosyl]oxy)-cis-9-octadecenoic acid 1',6"-lactone 6'-acrylate (213754-50-8)

Conditions	Yield
With zeolite; novozyme 435 In tetrahydrofuran at 35℃; for 96h; Product distribution / selectivity; Enzymatic reaction;	83%

vinyl acrylate (2177-18-6) + 1,2,3,4-Tetrahydro-1-naphthol (529-33-9) → Acrylic acid (R)-(1,2,3,4-tetrahydro-naphthalen-1-yl) ester (133832-53-8)

Conditions	Yield
In various solvent(s) at 25℃; for 4h; Pseudomonas sp. lipase;	82%

1N-HCl + aqueous sodium chloride + vinyl acrylate (2177-18-6) + sodium hydrogencarbonate (144-55-8) + 4-methoxy-phenol (150-76-5) + butanone (78-93-3) + Isosorbide (652-67-5) → 4-(2-hydroxyethoxy)benzoic acid (1711-24-6)

Conditions	Yield
lipase In tetrahydrofuran; hexane; dichloromethane	74%

vinyl acrylate (2177-18-6) + C11H15NO5S2 (1374110-34-5) → C14H17NO6S2 (1374110-35-6)

Conditions	Yield
With novozyme 435 In acetone at 50℃; Molecular sieve;	72%

vinyl acrylate (2177-18-6) + 2-phenylethanol (60-12-8) → 2-phenylethyl acrylate (3530-36-7)

Conditions	Yield
In 2,2,4-trimethylpentane at 37℃; immobilized lipase from Candida cylindracea;	66%

2-bromo-2-(2-ethyl)dioxolane (18742-02-4) + carbon monoxide (201230-82-2) + vinyl acrylate (2177-18-6) + allyltributylstanane (24850-33-7) → 2-Allyl-6-[1,3]dioxolan-2-yl-4-oxo-hexanoic acid vinyl ester

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In benzene at 80℃; under 38000 Torr; for 8h;	60%

vinyl acrylate (2177-18-6) + 2,3,4,5-tetrachlorothiophene-1,1-dioxide (72448-17-0) → 3a,4,5,6-tetrachloro-2,3,3a,6,7,7a-hexahydro-2-oxo-3,6-methanobenzofuran (72524-73-3)

Conditions	Yield
for 16h; Heating;	56%

3-methyl-2-oxo-1,2-dihydroquinoxaline (14003-34-0) + vinyl acrylate (2177-18-6) → (1S,2aS)-2a-Methyl-3-oxo-2,2a,3,4-tetrahydro-1H-azeto[1,2-a]quinoxaline-1-carboxylic acid vinyl ester (88392-75-0)

Conditions	Yield
In methanol; dichloromethane Ambient temperature; Irradiation;	50%

vinyl acrylate (2177-18-6) + (E)-1-phenyl-1,5-hexadien-3-ol (79299-29-9) → trans-(S)-1-phenyl-1,5-hexadien-3-ol (172925-28-9) + (1R)-1-[(E)-2-phenylvinyl]but-3-enyl acrylate (639798-55-3)

Conditions	Yield
With PS-Amano II In dichloromethane at 25℃; for 24h;	A 48% B 47%

vinyl acrylate (2177-18-6) + hexan-1-ol (111-27-3) → n-hexyl acrylate (2499-95-8)

Conditions	Yield
In 2,2,4-trimethylpentane at 37℃; immobilized lipase from Candida cylindracea;	40%
In 2,2,4-trimethylpentane at 37℃; immobilized lipase from Candida cylindracea; transesterification, other alcohols; also with vinyl methacrylate;	40%

vinyl acrylate (2177-18-6) + benzoyl chloride (98-88-4) → allyl 2-methyl-3-oxo-3-phenylpropanoate (883901-67-5)

Conditions	Yield
With Wilkinson's catalyst; 1,5-cis,cis-cyclooctadiene; diethylzinc In tetrahydrofuran; hexane at 0℃; for 24h; Reformatsky-Honda Reaction; Inert atmosphere;	40%

Upstream product

• 79-10-7 acrylic acid 
• 74-86-2 acetylene 
• 74-85-1 ethene 
• 5309-67-1 vinyl β-chloropropionate 
• 1119-20-6 divinylmercury 
• 108-05-4 vinyl acetate 

Downstream Products

• 1445-91-6 (S)-1-phenylethanol 
• 22639-28-7 (R)-goniothalamin 
• 13891-95-7 (1E,3R)-1-phenyl-1,5-hexadien-3-ol 
• 172925-28-9 trans-(S)-1-phenyl-1,5-hexadien-3-ol 
• 639798-55-3 (1R)-1-[(E)-2-phenylvinyl]but-3-enyl acrylate 
• 665003-66-7 (1S)-1-[(E)-2-phenylvinyl]but-3-enyl acrylate 
• 106-90-1 glycidyl acrylate 
• 883901-67-5 allyl 2-methyl-3-oxo-3-phenylpropanoate 
• 1711-24-6 4-(2-hydroxyethoxy)benzoic acid 
• 608523-23-5 6-benzyloxy-8,9-dihydro-6H-2,3,5,6,9a-pentaaza-benzo[cd]azulen-7-one 
• 2499-95-8 n-hexyl acrylate 
• 141-32-2 acrylic acid n-butyl ester 
• 2495-35-4 benzylacrylate 

Relevant articles and documents

Reusable rhodium catalyst for the selective transvinylation of sp2-C linked carboxylic acid

The vinyl benzoate derivatives were successfully synthesized by the transvinylation reactions that vinyl group transferred from vinyl acetate to aromatic carboxylic acids with the recoverable catalyst RhCl3·3H2O. This catalyst features air stable and tolerance of water, good reusable ability, meanwhile, shows high selectivity for aromatic carboxylic acid in the presence of phenolic hydroxyl. With this method, a variety of vinyl benzoate derivatives can be produced with up to 95% yield.

METHOD FOR PRODUCING CYCLIC UNSATURATED COMPOUND

The present invention provides a method for producing a cyclic unsaturated compound, which sufficiently suppresses generation of acyclic unsaturated compounds and permits excellent yield and reaction rate. Such a method for producing a cyclic unsaturated compound is a method for producing a cyclic unsaturated compound by reacting an a, ?-unsaturated carboxylic acid with an unsaturated organic compound, wherein the method comprises a step of reacting the a, ?-unsaturated carboxylic acid with the unsaturated organic compound in the presence of a catalyst.

Method for the preparation of alkenyl esters of carboxylic acids

A novel and effective catalyst system is provided for application in the preparation of alkenyl esters of carboxylic acids by transesterification reaction. The catalyst system consists of a palladium compound as the main ingredient and a cocatalyst formed of an alkali metal compound and a copper compound, at least one of which is a halide. The catalyst ingredients are adsorbed on a solid catalyst carrier, so that repeated use of the combined catalyst or a continuous operation of the reaction can easily be facilitated.