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868-77-9 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.]

Check Digit Verification of cas no

The CAS Registry Mumber 868-77-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 8,6 and 8 respectively; the second part has 2 digits, 7 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 868-77:
(5*8)+(4*6)+(3*8)+(2*7)+(1*7)=109
109 % 10 = 9
So 868-77-9 is a valid CAS Registry Number.
InChI:InChI=1/C6H10O3/c1-4(2)6(8)9-5(3)7/h5,7H,1H2,2-3H3

868-77-9 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (M0085)  2-Hydroxyethyl Methacrylate (stabilized with MEHQ)  >95.0%(GC)

  • 868-77-9

  • 25g

  • 120.00CNY

  • Detail
  • TCI America

  • (M0085)  2-Hydroxyethyl Methacrylate (stabilized with MEHQ)  >95.0%(GC)

  • 868-77-9

  • 500g

  • 290.00CNY

  • Detail
  • Alfa Aesar

  • (B24260)  2-Hydroxyethyl methacrylate, 97%, stab. with 4-methoxyphenol   

  • 868-77-9

  • 100g

  • 197.0CNY

  • Detail
  • Alfa Aesar

  • (B24260)  2-Hydroxyethyl methacrylate, 97%, stab. with 4-methoxyphenol   

  • 868-77-9

  • 500g

  • 331.0CNY

  • Detail
  • Aldrich

  • (477028)  2-Hydroxyethylmethacrylate  ≥99%, contains ≤50 ppm monomethyl ether hydroquinone as inhibitor

  • 868-77-9

  • 477028-25ML

  • 542.88CNY

  • Detail
  • Aldrich

  • (477028)  2-Hydroxyethylmethacrylate  ≥99%, contains ≤50 ppm monomethyl ether hydroquinone as inhibitor

  • 868-77-9

  • 477028-100ML

  • 610.74CNY

  • Detail
  • Aldrich

  • (128635)  2-Hydroxyethylmethacrylate  contains ≤250 ppm monomethyl ether hydroquinone as inhibitor, 97%

  • 868-77-9

  • 128635-500G

  • 407.16CNY

  • Detail
  • Aldrich

  • (128635)  2-Hydroxyethylmethacrylate  contains ≤250 ppm monomethyl ether hydroquinone as inhibitor, 97%

  • 868-77-9

  • 128635-1KG

  • 478.53CNY

  • Detail
  • Aldrich

  • (128635)  2-Hydroxyethylmethacrylate  contains ≤250 ppm monomethyl ether hydroquinone as inhibitor, 97%

  • 868-77-9

  • 128635-18KG

  • 5,039.19CNY

  • Detail

868-77-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Nov 28, 2017

Revision Date: Nov 28, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-hydroxyethyl methacrylate

1.2 Other means of identification

Product number -
Other names 2-Hydroxyethyl methacrylate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.Adhesives and sealant chemicals,Intermediates,Paint additives and coating additives not described by other categories,Photosensitive chemicals
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:868-77-9 SDS

868-77-9Synthetic route

ethylene glycol
107-21-1

ethylene glycol

methacrylic acid methyl ester
80-62-6

methacrylic acid methyl ester

A

2-methyl-2-propenoic acid 2-hydroxyethyl ester
868-77-9

2-methyl-2-propenoic acid 2-hydroxyethyl ester

B

EDMA
97-90-5

EDMA

Conditions
ConditionsYield
With 10H-phenothiazine; toluene-4-sulfonic acid at 100℃; for 2.5h; Temperature; Time;A 97.18%
B 2.82%
oxirane
75-21-8

oxirane

poly(methacrylic acid)
79-41-4

poly(methacrylic acid)

2-methyl-2-propenoic acid 2-hydroxyethyl ester
868-77-9

2-methyl-2-propenoic acid 2-hydroxyethyl ester

Conditions
ConditionsYield
4-hydroxy-TEMPO benzoate at 100℃; for 4h;95%
With water; triethylamine at 125℃;
With pyridine; copper diacetate
oxirane
75-21-8

oxirane

poly(methacrylic acid)
79-41-4

poly(methacrylic acid)

A

2-methyl-2-propenoic acid 2-hydroxyethyl ester
868-77-9

2-methyl-2-propenoic acid 2-hydroxyethyl ester

B

2-(2-hydroxyethoxy)ethyl methacrylate
2351-43-1

2-(2-hydroxyethoxy)ethyl methacrylate

Conditions
ConditionsYield
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

2-methyllactic acid

ethylene glycol
107-21-1

ethylene glycol

2-methyl-2-propenoic acid 2-hydroxyethyl ester
868-77-9

2-methyl-2-propenoic acid 2-hydroxyethyl ester

Conditions
ConditionsYield
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

poly(methacrylic acid)

ethylene glycol
107-21-1

ethylene glycol

2-methyl-2-propenoic acid 2-hydroxyethyl ester
868-77-9

2-methyl-2-propenoic acid 2-hydroxyethyl ester

Conditions
ConditionsYield
With iodine for 4h; Reflux;85%
With toluene-4-sulfonic acid In benzene Heating;
methyl 2-hydroxy-2-methylpropionate
2110-78-3

methyl 2-hydroxy-2-methylpropionate

ethylene glycol
107-21-1

ethylene glycol

2-methyl-2-propenoic acid 2-hydroxyethyl ester
868-77-9

2-methyl-2-propenoic acid 2-hydroxyethyl ester

Conditions
ConditionsYield
calcinated cesium nitrate on silica at 330℃; Gas phase;62.9%
2-ethylhexyl α-hydroxyisobutyrate

2-ethylhexyl α-hydroxyisobutyrate

ethylene glycol
107-21-1

ethylene glycol

2-methyl-2-propenoic acid 2-hydroxyethyl ester
868-77-9

2-methyl-2-propenoic acid 2-hydroxyethyl ester

Conditions
ConditionsYield
calcinated cesium nitrate on silicate at 340℃; Gas phase;58.7%
ethylene glycol
107-21-1

ethylene glycol

ethyl 2-hydroxy-2,2-dimethylethanoate
80-55-7

ethyl 2-hydroxy-2,2-dimethylethanoate

2-methyl-2-propenoic acid 2-hydroxyethyl ester
868-77-9

2-methyl-2-propenoic acid 2-hydroxyethyl ester

Conditions
ConditionsYield
calcinated cesium nitrate on silicate Gas phase;54.9%
1,2-propanediene
463-49-0

1,2-propanediene

carbon monoxide
201230-82-2

carbon monoxide

ethylene glycol
107-21-1

ethylene glycol

A

2,2-dimethyl-1,3-dioxolane
2916-31-6

2,2-dimethyl-1,3-dioxolane

B

2-methyl-2-propenoic acid 2-hydroxyethyl ester
868-77-9

2-methyl-2-propenoic acid 2-hydroxyethyl ester

Conditions
ConditionsYield
dodecacarbonyl-triangulo-triruthenium at 100℃; for 3h;A 52%
B 8%
ethylene glycol
107-21-1

ethylene glycol

methacrylic acid methyl ester
80-62-6

methacrylic acid methyl ester

2-methyl-2-propenoic acid 2-hydroxyethyl ester
868-77-9

2-methyl-2-propenoic acid 2-hydroxyethyl ester

Conditions
ConditionsYield
With toluene-4-sulfonic acid at 170℃;
poly(methacrylic acid)
79-41-4

poly(methacrylic acid)

2-chloro-ethanol
107-07-3

2-chloro-ethanol

2-methyl-2-propenoic acid 2-hydroxyethyl ester
868-77-9

2-methyl-2-propenoic acid 2-hydroxyethyl ester

Conditions
ConditionsYield
With sodium carbonate; copper(l) chloride
potassium methacrylate
6900-35-2

potassium methacrylate

2-chloro-ethanol
107-07-3

2-chloro-ethanol

2-methyl-2-propenoic acid 2-hydroxyethyl ester
868-77-9

2-methyl-2-propenoic acid 2-hydroxyethyl ester

Conditions
ConditionsYield
With copper(l) chloride
1-methacryloyloxy-2-vinyloxy-ethane

1-methacryloyloxy-2-vinyloxy-ethane

2-methyl-2-propenoic acid 2-hydroxyethyl ester
868-77-9

2-methyl-2-propenoic acid 2-hydroxyethyl ester

Conditions
ConditionsYield
With sulfuric acid
poly(methacrylic acid)
79-41-4

poly(methacrylic acid)

ethylene dioxide

ethylene dioxide

2-methyl-2-propenoic acid 2-hydroxyethyl ester
868-77-9

2-methyl-2-propenoic acid 2-hydroxyethyl ester

Conditions
ConditionsYield
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

2-chloro-ethanol

potassium methacrylate

potassium methacrylate

2-methyl-2-propenoic acid 2-hydroxyethyl ester
868-77-9

2-methyl-2-propenoic acid 2-hydroxyethyl ester

Conditions
ConditionsYield
With hydroquinone at 105 - 108℃;
ethylene glycol
107-21-1

ethylene glycol

Methacryloyl chloride
920-46-7

Methacryloyl chloride

2-methyl-2-propenoic acid 2-hydroxyethyl ester
868-77-9

2-methyl-2-propenoic acid 2-hydroxyethyl ester

Conditions
ConditionsYield
In toluene at 29.85 - 59.85℃; Kinetics; Thermodynamic data; Acylation;
10H-phenothiazine
92-84-2

10H-phenothiazine

poly(methacrylic acid)
79-41-4

poly(methacrylic acid)

A

2-methyl-2-propenoic acid 2-hydroxyethyl ester
868-77-9

2-methyl-2-propenoic acid 2-hydroxyethyl ester

B

2-(2-hydroxyethoxy)ethyl methacrylate
2351-43-1

2-(2-hydroxyethoxy)ethyl methacrylate

C

EDMA
97-90-5

EDMA

Conditions
ConditionsYield
chromium(II) acetate at 70℃; under 7500.75 Torr; for 5.5h;
oxirane
75-21-8

oxirane

poly(methacrylic acid)
79-41-4

poly(methacrylic acid)

A

2-methyl-2-propenoic acid 2-hydroxyethyl ester
868-77-9

2-methyl-2-propenoic acid 2-hydroxyethyl ester

B

2-hydroxyethyl acetate
542-59-6

2-hydroxyethyl acetate

C

2-(2-hydroxyethoxy)ethyl methacrylate
2351-43-1

2-(2-hydroxyethoxy)ethyl methacrylate

D

EDMA
97-90-5

EDMA

Conditions
ConditionsYield
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

2,4-toluene

polydiethylene hexamethylenedicarbamate

polydiethylene hexamethylenedicarbamate

ethylene glycol
107-21-1

ethylene glycol

dianhydride of benzophenone-3,4,3',4'-tetracarboxy acid
2421-28-5

dianhydride of benzophenone-3,4,3',4'-tetracarboxy acid

2-methyl-2-propenoic acid 2-hydroxyethyl ester
868-77-9

2-methyl-2-propenoic acid 2-hydroxyethyl ester

Conditions
ConditionsYield
stannous octoate; hydroquinone In tetrahydrofuran
oxirane
75-21-8

oxirane

poly(methacrylic acid)
79-41-4

poly(methacrylic acid)

A

2-methyl-2-propenoic acid 2-hydroxyethyl ester
868-77-9

2-methyl-2-propenoic acid 2-hydroxyethyl ester

B

EDMA
97-90-5

EDMA

Conditions
ConditionsYield
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

methanol

C26H59NO10P2Si4
1279116-11-8

C26H59NO10P2Si4

A

2-methyl-2-propenoic acid 2-hydroxyethyl ester
868-77-9

2-methyl-2-propenoic acid 2-hydroxyethyl ester

B

C14H27NO10P2
1279116-04-9

C14H27NO10P2

C

6-hexanoic acid

6-hexanoic acid

Conditions
ConditionsYield
at 20℃; for 2h;
methanol
67-56-1

methanol

C31H69NO10P2Si4
1279116-12-9

C31H69NO10P2Si4

A

2-methyl-2-propenoic acid 2-hydroxyethyl ester
868-77-9

2-methyl-2-propenoic acid 2-hydroxyethyl ester

B

iminobis(methylenephosphono)undecanoic acid

iminobis(methylenephosphono)undecanoic acid

C

C19H37NO10P2
1279116-05-0

C19H37NO10P2

Conditions
ConditionsYield
at 20℃; for 2h;
C18H35NO10P2
1279115-96-6

C18H35NO10P2

A

2-methyl-2-propenoic acid 2-hydroxyethyl ester
868-77-9

2-methyl-2-propenoic acid 2-hydroxyethyl ester

B

6-hexanoic acid

6-hexanoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: chloroform / 16 h / 20 °C
2: 2 h / 20 °C
View Scheme
C23H45NO10P2
1279115-97-7

C23H45NO10P2

A

2-methyl-2-propenoic acid 2-hydroxyethyl ester
868-77-9

2-methyl-2-propenoic acid 2-hydroxyethyl ester

B

C19H37NO10P2
1279116-05-0

C19H37NO10P2

Conditions
ConditionsYield
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-acetoxyethyl methylacrylate

2-methyl-2-propenoic acid 2-hydroxyethyl ester
868-77-9

2-methyl-2-propenoic acid 2-hydroxyethyl ester

Conditions
ConditionsYield
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

2,2-(2-nitro-1,4-phenylene)bis(methylene)bis(oxy) bis(oxomethylene)bis(oxy)bis(ethane-2,1-diyl) bis(2-methylacrylate)

A

2-methyl-2-propenoic acid 2-hydroxyethyl ester
868-77-9

2-methyl-2-propenoic acid 2-hydroxyethyl ester

B

C15H15NO7

C15H15NO7

Conditions
ConditionsYield
In tetrahydrofuran for 10h; Kinetics; UV-irradiation;
2-(methacryloyloxy)ethyl acetoacetate
21282-97-3

2-(methacryloyloxy)ethyl acetoacetate

2-methyl-2-propenoic acid 2-hydroxyethyl ester
868-77-9

2-methyl-2-propenoic acid 2-hydroxyethyl ester

Conditions
ConditionsYield
With water at 90℃; for 54h; Reactivity;
2-(methacryloyloxy)ethyl acetoacetate
21282-97-3

2-(methacryloyloxy)ethyl acetoacetate

A

2-methyl-2-propenoic acid 2-hydroxyethyl ester
868-77-9

2-methyl-2-propenoic acid 2-hydroxyethyl ester

B

acetone
67-64-1

acetone

Conditions
ConditionsYield
With water at 90℃; for 54h; Reactivity;
2-methyl-2-propenoic acid 2-hydroxyethyl ester
868-77-9

2-methyl-2-propenoic acid 2-hydroxyethyl ester

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

2-[(methylsulfonyl)oxy]ethyl 2-methylacrylate
16081-17-7

2-[(methylsulfonyl)oxy]ethyl 2-methylacrylate

Conditions
ConditionsYield
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

2-methyl-2-propenoic acid 2-hydroxyethyl ester

succinic acid anhydride
108-30-5

succinic acid anhydride

2-methacryloyloxyethyl hydrogen succinate
20882-04-6

2-methacryloyloxyethyl hydrogen succinate

Conditions
ConditionsYield
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

2-methyl-2-propenoic acid 2-hydroxyethyl ester

methacrylic acid methyl ester
80-62-6

methacrylic acid methyl ester

polymer; monomers: 2-hydroxyethyl methacrylate; methyl methacrylate

polymer; monomers: 2-hydroxyethyl methacrylate; methyl methacrylate

Conditions
ConditionsYield
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%

868-77-9Relevant articles and documents

BIOGUM AND BOTANICAL GUM HYDROGEL BIOINKS FOR THE PHYSIOLOGICAL 3D BIOPRINTING OF TISSUE CONSTRUCTS FOR IN VITRO CULTURE AND TRANSPLANTATION

-

, (2021/01/20)

Bioink compositions comprising a biomaterial (mammalian, plant based, synthetically derived, or microbially derived) such as a hydrogel and a microbial-, fungal-, or plant-produced polysaccharide, with or without cells, for use in the 3D bioprinting of human tissues and scaffolds are described. The bioink compositions have excellent printability and improved cell function, viability and engraftment. Furthermore, the bioink compositions can be supplemented through the additional of auxiliary proteins and other molecules such as growth factors including extracellular matrix components, Laminins, super affinity growth factors and morphogens. The bioink compositions can be used under physiological conditions related to 3D bioprinting parameters which are cytocompatible (e.g. temperature, printing pressure, nozzle size, bioink gelation process). The combination of a biogum-based biomaterial together with mammalian, plant, microbial or synthetically derived hydrogels exhibited improvement in printability, cell function and viability compared to tissues printed with bioink not containing biogums.

Runge-Kutta analysis for optimizing the Zn-catalyzed transesterification conditions of MA and MMA with diols to maximize monoesterified products

Kato, Taito,Akebi, Shin-Ya,Nagae, Haruki,Yonehara, Koji,Oku, Tomoharu,Mashima, Kazushi

, p. 6975 - 6986 (2021/11/17)

Terminal hydroxylated acrylates and methacrylates were prepared by catalytic transesterification of acrylates and methacrylates with diols catalyzed by a system of a tetranuclear zinc alkoxide, [Zn(tmhd)(OMe)(MeOH)]4 (1a), with 4 equiv. of 2,2′-bipyridine (L1). The reaction time to reach the equilibrium state was analyzed by kinetic studies and a curve-fitting analysis based on the Runge-Kutta method for optimizing the best reaction conditions for mono-esterification. In addition to these kinetic analyses, DFT calculations estimated a proposed mechanism of the catalytic transesterification. This journal is

METHOD FOR PREPARING HYDROXYETHYL (METH) ACRYLATE

-

Paragraph 0033; 0034, (2017/07/14)

Hydroxyethyl (methyl)acrylate is prepared by a process of a combination of a three-stage tubular reactor and a tower reactor, wherein, firstly, a catalyst, a polymerization inhibitor and (methyl) acrylic acid are mixed until the solids are dissolved, then mixed with a part of ethylene oxide and thereafter enter into a first tubular reactor for a reaction, a reaction liquid flowing out from the first tubular reactor is mixed with a certain amount of ethylene oxide and enters into a second tubular reactor for a reaction, a reaction liquid flowing out from the second tubular reactor is then mixed with a certain amount of ethylene oxide and thereafter enters into a third tubular reactor, and a reaction liquid flowing out from the third tubular reactor is then passed through a stage of an adiabatic tower reactor and aged such that a product liquid is obtained from extraction.

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