868-77-9

Basic information

• Product Name: 2-Hydroxyethyl methacrylate
• Synonyms: 1,2-Ethanediol, mono(2-methyl)-2-propenoate-;2-(Methacryloyloxy)ethanol;2-Hydroxyethyl 2-methylacrylate;2-Hydroxyethyl-2-methyl-2-propenoate;2-Methyl-2-propenoic acid, 2-hydroxyethyl ester;2-methyl-2-propenoicaci2-hydroxyethylester;2-Propenoic acid, 2-methyl-, 2-hydroxyethyl ester;2-Propenoicacid,2-methyl-,2-hydroxyethylester
• CAS NO: 868-77-9
• Molecular Formula: C₆H₁₀O₃
• Molecular Weight: 130.14
• EINECS: 212-782-2
• Product Categories: Industrial/Fine Chemicals;Aliphatics;Mutagenesis Research Chemicals
• Mol File: 868-77-9.mol
• Article Data: 36

Chemical Properties

• Melting Point: -12 °C
• Boiling Point: 67 °C3.5 mm Hg(lit.)
• Flash Point: 207 °F
• Appearance: Clear/Liquid
• Density: 1.073 g/mL at 25 °C(lit.)
• Vapor Density: 5 (vs air)
• Vapor Pressure: 0.01 mm Hg ( 25 °C)
• Refractive Index: n20/D 1.453(lit.)
• Storage Temp.: 2-8°C
• Solubility: Chloroform, Methanol (Slightly)
• PKA: 13.83±0.10(Predicted)
• Water Solubility: soluble
• Sensitive: Air Sensitive
• Stability: Unstable - may polymerize in the absence of stabilizer. May be stabilized with, or contain small amounts of, diethylene glycol m
• BRN: 1071583
• CAS DataBase Reference: 2-Hydroxyethyl methacrylate(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Hydroxyethyl methacrylate(868-77-9)
• EPA Substance Registry System: 2-Hydroxyethyl methacrylate(868-77-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/38-43-36/37/38
• Safety Statements: 26-36/37-28A-28
• WGK Germany: 1
• RTECS: OZ4725000
• F: 8
• TSCA: Yes
• Hazardous Substances Data: 868-77-9(Hazardous Substances Data)

Usage

Chemical Properties

colourless liquid

Uses

Different sources of media describe the Uses of 868-77-9 differently. You can refer to the following data:
1. 2-Hydroxyethyl methacrylate is used for preparation of hydrophilic polymers for biomedical devices.
2. 2-Hydroxyethyl methacrylate is the methacrylic monomer for use in UV inks, adhesives, lacquers, dental materials, artificial nails, etc.
3. 2-Hydroxyethyl methacrylate is used in UV-curable inks and coatings. It is also used in adhesives, artificial nails, dental materials and lacquers. In dentistry, it is one of the main volatile acrylates along with methyl methacrylate. Further, it is used as a monomer in the synthesis of polymers for dental prosthetics and for geotechnical grouting in construction work.

Definition

2-Hydroxyethyl methacrylate is an enoate ester that is the monomethacryloyl derivative of ethylene glycol.

General Description

2-Hydroxyethyl methacrylate (HEMA) is biocompatible in nature. Polymeric hydrogel scaffold can be produced by polymerizing HEMA in water.

Hazard

30% grade (with xylene): Flammable, moderate fire risk.

Purification Methods

Dissolve the ester in water and extract with n-heptane to remove ethylene glycol dimethacrylate (checked by gas-liquid chromatography and by NMR) and distil it twice under reduced pressure [Strop et al. J Phys Chem 80 694 1976]. [Beilstein 2 IV 1530.]

InChI:InChI=1/C6H10O3/c1-4(2)6(8)9-5(3)7/h5,7H,1H2,2-3H3

Synthetic route

ethylene glycol (107-21-1) + methacrylic acid methyl ester (80-62-6) → 2-methyl-2-propenoic acid 2-hydroxyethyl ester (868-77-9) + EDMA (97-90-5)

Conditions	Yield
With 10H-phenothiazine; toluene-4-sulfonic acid at 100℃; for 2.5h; Temperature; Time;	A 97.18% B 2.82%

oxirane (75-21-8) + poly(methacrylic acid) (79-41-4) → 2-methyl-2-propenoic acid 2-hydroxyethyl ester (868-77-9)

Conditions	Yield
4-hydroxy-TEMPO benzoate at 100℃; for 4h;	95%
With water; triethylamine at 125℃;
With pyridine; copper diacetate

oxirane (75-21-8) + poly(methacrylic acid) (79-41-4) → 2-methyl-2-propenoic acid 2-hydroxyethyl ester (868-77-9) + 2-(2-hydroxyethoxy)ethyl methacrylate (2351-43-1)

Conditions	Yield
With triethanolamine; poly(ferric methacrylate); choline chloride In water at 30 - 66℃; for 5.53h;	A 93.9% B n/a

2-methyllactic acid (594-61-6) + ethylene glycol (107-21-1) → 2-methyl-2-propenoic acid 2-hydroxyethyl ester (868-77-9)

Conditions	Yield
calcinated cesium carbonate and titan oxide on silica at 320℃; Gas phase;	90.4%
calcinated cesium nitrate on silica In water at 320℃; Gas phase;	89.2%
at 320℃; Gas phase;	88%

poly(methacrylic acid) (79-41-4) + ethylene glycol (107-21-1) → 2-methyl-2-propenoic acid 2-hydroxyethyl ester (868-77-9)

Conditions	Yield
With iodine for 4h; Reflux;	85%
With toluene-4-sulfonic acid In benzene Heating;

methyl 2-hydroxy-2-methylpropionate (2110-78-3) + ethylene glycol (107-21-1) → 2-methyl-2-propenoic acid 2-hydroxyethyl ester (868-77-9)

Conditions	Yield
calcinated cesium nitrate on silica at 330℃; Gas phase;	62.9%

2-ethylhexyl α-hydroxyisobutyrate + ethylene glycol (107-21-1) → 2-methyl-2-propenoic acid 2-hydroxyethyl ester (868-77-9)

Conditions	Yield
calcinated cesium nitrate on silicate at 340℃; Gas phase;	58.7%

ethylene glycol (107-21-1) + ethyl 2-hydroxy-2,2-dimethylethanoate (80-55-7) → 2-methyl-2-propenoic acid 2-hydroxyethyl ester (868-77-9)

Conditions	Yield
calcinated cesium nitrate on silicate Gas phase;	54.9%

1,2-propanediene (463-49-0) + carbon monoxide (201230-82-2) + ethylene glycol (107-21-1) → 2,2-dimethyl-1,3-dioxolane (2916-31-6) + 2-methyl-2-propenoic acid 2-hydroxyethyl ester (868-77-9)

Conditions	Yield
dodecacarbonyl-triangulo-triruthenium at 100℃; for 3h;	A 52% B 8%

ethylene glycol (107-21-1) + methacrylic acid methyl ester (80-62-6) → 2-methyl-2-propenoic acid 2-hydroxyethyl ester (868-77-9)

Conditions	Yield
With toluene-4-sulfonic acid at 170℃;

poly(methacrylic acid) (79-41-4) + 2-chloro-ethanol (107-07-3) → 2-methyl-2-propenoic acid 2-hydroxyethyl ester (868-77-9)

Conditions	Yield
With sodium carbonate; copper(l) chloride

potassium methacrylate (6900-35-2) + 2-chloro-ethanol (107-07-3) → 2-methyl-2-propenoic acid 2-hydroxyethyl ester (868-77-9)

Conditions	Yield
With copper(l) chloride

1-methacryloyloxy-2-vinyloxy-ethane → 2-methyl-2-propenoic acid 2-hydroxyethyl ester (868-77-9)

Conditions	Yield
With sulfuric acid

poly(methacrylic acid) (79-41-4) + ethylene dioxide → 2-methyl-2-propenoic acid 2-hydroxyethyl ester (868-77-9)

Conditions	Yield
With iron tris-<2-chloro ethylate>; iron(III) chloride
With pyridine; benzene
With sodium methylate
With iron tris-<2-chloro ethylate>; iron(III) chloride

2-chloro-ethanol (107-07-3) + potassium methacrylate → 2-methyl-2-propenoic acid 2-hydroxyethyl ester (868-77-9)

Conditions	Yield
With hydroquinone at 105 - 108℃;

ethylene glycol (107-21-1) + Methacryloyl chloride (920-46-7) → 2-methyl-2-propenoic acid 2-hydroxyethyl ester (868-77-9)

Conditions	Yield
In toluene at 29.85 - 59.85℃; Kinetics; Thermodynamic data; Acylation;

10H-phenothiazine (92-84-2) + poly(methacrylic acid) (79-41-4) → 2-methyl-2-propenoic acid 2-hydroxyethyl ester (868-77-9) + 2-(2-hydroxyethoxy)ethyl methacrylate (2351-43-1) + EDMA (97-90-5)

Conditions	Yield
chromium(II) acetate at 70℃; under 7500.75 Torr; for 5.5h;

oxirane (75-21-8) + poly(methacrylic acid) (79-41-4) → 2-methyl-2-propenoic acid 2-hydroxyethyl ester (868-77-9) + 2-hydroxyethyl acetate (542-59-6) + 2-(2-hydroxyethoxy)ethyl methacrylate (2351-43-1) + EDMA (97-90-5)

Conditions	Yield
10H-phenothiazine; chromium(lll) acetate at 60 - 80℃; under 750.075 Torr; for 6.1h; Autoclave;	A 96.0 %Chromat. B 0.3 %Chromat. C 3.7 %Chromat. D 0.08 %Chromat.

2,4-toluene + polydiethylene hexamethylenedicarbamate + ethylene glycol (107-21-1) + dianhydride of benzophenone-3,4,3',4'-tetracarboxy acid (2421-28-5) → 2-methyl-2-propenoic acid 2-hydroxyethyl ester (868-77-9)

Conditions	Yield
stannous octoate; hydroquinone In tetrahydrofuran

oxirane (75-21-8) + poly(methacrylic acid) (79-41-4) → 2-methyl-2-propenoic acid 2-hydroxyethyl ester (868-77-9) + EDMA (97-90-5)

Conditions	Yield
With 4-methoxy-phenol; chromium silicylate at 80℃; for 3h; autoclave;
With triethanolamine; poly(ferric methacrylate); choline chloride In water at 30 - 66℃; for 5.95h;	A 90.9 %Chromat. B n/a

methanol (67-56-1) + C26H59NO10P2Si4 (1279116-11-8) → 2-methyl-2-propenoic acid 2-hydroxyethyl ester (868-77-9) + C14H27NO10P2 (1279116-04-9) + 6-hexanoic acid

Conditions	Yield
at 20℃; for 2h;

methanol (67-56-1) + C31H69NO10P2Si4 (1279116-12-9) → 2-methyl-2-propenoic acid 2-hydroxyethyl ester (868-77-9) + iminobis(methylenephosphono)undecanoic acid + C19H37NO10P2 (1279116-05-0)

Conditions	Yield
at 20℃; for 2h;

C18H35NO10P2 (1279115-96-6) → 2-methyl-2-propenoic acid 2-hydroxyethyl ester (868-77-9) + 6-hexanoic acid

Conditions	Yield
Multi-step reaction with 2 steps 1: chloroform / 16 h / 20 °C 2: 2 h / 20 °C View Scheme

C23H45NO10P2 (1279115-97-7) → 2-methyl-2-propenoic acid 2-hydroxyethyl ester (868-77-9) + C19H37NO10P2 (1279116-05-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: chloroform / 16 h / 20 °C 2: 2 h / 20 °C View Scheme

2-acetoxyethyl methylacrylate (20166-49-8) → 2-methyl-2-propenoic acid 2-hydroxyethyl ester (868-77-9)

Conditions	Yield
With methanol at 20℃; for 4h;

2,2-(2-nitro-1,4-phenylene)bis(methylene)bis(oxy) bis(oxomethylene)bis(oxy)bis(ethane-2,1-diyl) bis(2-methylacrylate) (1269794-11-7) → 2-methyl-2-propenoic acid 2-hydroxyethyl ester (868-77-9) + C15H15NO7

Conditions	Yield
In tetrahydrofuran for 10h; Kinetics; UV-irradiation;

2-(methacryloyloxy)ethyl acetoacetate (21282-97-3) → 2-methyl-2-propenoic acid 2-hydroxyethyl ester (868-77-9)

Conditions	Yield
With water at 90℃; for 54h; Reactivity;

2-(methacryloyloxy)ethyl acetoacetate (21282-97-3) → 2-methyl-2-propenoic acid 2-hydroxyethyl ester (868-77-9) + acetone (67-64-1)

Conditions	Yield
With water at 90℃; for 54h; Reactivity;

2-methyl-2-propenoic acid 2-hydroxyethyl ester (868-77-9) + methanesulfonyl chloride (124-63-0) → 2-[(methylsulfonyl)oxy]ethyl 2-methylacrylate (16081-17-7)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 4.5h;	100%
With triethylamine In diethyl ether at 0 - 5℃; for 0.25h;	90.5%
With triethylamine In tetrahydrofuran at 0 - 20℃;	37.5 g

2-methyl-2-propenoic acid 2-hydroxyethyl ester (868-77-9) + succinic acid anhydride (108-30-5) → 2-methacryloyloxyethyl hydrogen succinate (20882-04-6)

Conditions	Yield
With 4-methoxy-phenol at 90℃; for 18h;	100%
With 4-methoxy-phenol In neat (no solvent) at 90℃; for 18h; Inert atmosphere; Sealed tube;	100%
With pyridine; dmap In tetrahydrofuran at 20 - 40℃; for 24h; Schlenk technique; Inert atmosphere;	95%

2-methyl-2-propenoic acid 2-hydroxyethyl ester (868-77-9) + methacrylic acid methyl ester (80-62-6) → polymer; monomers: 2-hydroxyethyl methacrylate; methyl methacrylate

Conditions	Yield
2,2'-azobis(isobutyronitrile) In butanone at 64.85℃; for 4h; Activation energy; Kinetics; Product distribution; Further Variations:; Temperatures; times; Polymerization;	100%
2,2'-azobis(isobutyronitrile) In butanone at 64.85℃; for 4h; Polymerization;	100%

Upstream product

• 75-21-8 oxirane 
• 79-41-4 poly(methacrylic acid) 
• 107-21-1 ethylene glycol 
• 80-62-6 methacrylic acid methyl ester 
• 107-07-3 2-chloro-ethanol 
• 6900-35-2 potassium methacrylate 
• 920-46-7 Methacryloyl chloride 
• 463-49-0 1,2-propanediene 
• 201230-82-2 carbon monoxide 
• 80-55-7 ethyl 2-hydroxy-2,2-dimethylethanoate 
• 594-61-6 2-methyllactic acid 
• 2110-78-3 methyl 2-hydroxy-2-methylpropionate 
• 92-84-2 10H-phenothiazine 
• 2421-28-5 dianhydride of benzophenone-3,4,3',4'-tetracarboxy acid 

Downstream Products

• 19117-13-6 2-Methyl-acrylic acid 2-(heptyl-{4-[1-(4-{heptyl-[2-(2-methyl-acryloyloxy)-ethoxy]-phosphinoyloxy}-phenyl)-1-methyl-ethyl]-phenoxy}-phosphinoyloxy)-ethyl ester 
• 97789-13-4 Phosphorsaeure-diisoamylester-(2-methacryloyloxy-ethylester) 
• 814-26-6 Phosphorsaeure-diisobutylester-(2-methacryloyloxy-ethylester) 
• 15458-75-0 2-(methacryloyloxy)ethyl phosphate 
• 814-35-7 2-[(diethoxyphosphinyl)oxy]ethyl methacrylate 
• 91695-23-7 Phosphorsaeure-diisopropylester-(2-methacryloyloxy-ethylester) 
• 814-34-6 2-(O,O-Dipropyl-phosphonooxy)-1-methacryloyloxy-ethan 
• 42040-45-9 2-Methyl-acrylic acid 2-benzenesulfonyloxy-ethyl ester 
• 10552-43-9 α,ω-bis(methacryloylethyleneglycol)phthalate 
• 35703-81-2 β-(methacryloxy)ethyl p-cetoxycinnamate 
• 35703-96-9 p-Phenoxyzimtsaeure-α-methacryloxyethylester 
• 35703-84-5 (E)-3-(4-Hexadecyloxy-phenyl)-2-methyl-acrylic acid 2-(2-methyl-acryloyloxy)-ethyl ester 
• 108595-19-3 1-hexa-2t,4t-dienyloxy-2-methacryloyloxy-ethane 

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