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868-77-9

Basic Information
CAS No.: 868-77-9
Name: 2-Propenoicacid, 2-methyl-, 2-hydroxyethyl ester
Molecular Structure:
Molecular Structure of 868-77-9 (2-Propenoicacid, 2-methyl-, 2-hydroxyethyl ester)
Formula: C6H10O3
Molecular Weight: 130.16
Synonyms: GE 610;2-HYDROXYETHL METHACRYLATE;ETHYLENE GLYCOL METHACRYLATE;2-Hydroxyethyl methacrylate;HYDROXYETHYL METHACRYLATE;ETHYLENEGLYCOL METHACRYLATE (HEMA);ethylene glycol monomethacrylate;GMA;hydroxy ethyl methacrylate;BisoMer SR;ethylene glycol methacrylate;METHACRYLIC ACID 2-HYDROXYETHYL ESTER;methanol,methyl methacrylate;2-HYDROXYETHYLMETHACRYLATE;2-HYDROXYETHYL METHACRYLATE (2-HEMA);2-hydroxyethyl 2-methylprop-2-enoate;
EINECS: 212-782-2
Density: 1.054 g/cm3
Melting Point: -12 °C
Boiling Point: 189.031 °C at 760 mmHg
Flash Point: 97.222 °C
Solubility: soluble in water
Appearance: colourless liquid
Hazard Symbols: IrritantXi
Risk Codes: 36/38-43-36/37/38
Safety: 26-36/37-28A-28
Transport Information:
PSA: 46.53000
LogP: 0.09800
Synthetic route
107-21-1

ethylene glycol

80-62-6

methacrylic acid methyl ester

A

868-77-9

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

B

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%
75-21-8

oxirane

79-41-4

poly(methacrylic acid)

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
75-21-8

oxirane

79-41-4

poly(methacrylic acid)

A

868-77-9

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

B

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
594-61-6

2-methyllactic acid

107-21-1

ethylene glycol

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%
79-41-4

poly(methacrylic acid)

107-21-1

ethylene glycol

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;
2110-78-3

methyl 2-hydroxy-2-methylpropionate

107-21-1

ethylene glycol

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

107-21-1

ethylene glycol

868-77-9

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

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

ethylene glycol

80-55-7

ethyl 2-hydroxy-2,2-dimethylethanoate

868-77-9

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

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

1,2-propanediene

201230-82-2

carbon monoxide

107-21-1

ethylene glycol

A

2916-31-6

2,2-dimethyl-1,3-dioxolane

B

868-77-9

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

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

ethylene glycol

80-62-6

methacrylic acid methyl ester

868-77-9

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

Conditions
ConditionsYield
With toluene-4-sulfonic acid at 170℃;
79-41-4

poly(methacrylic acid)

107-07-3

2-chloro-ethanol

868-77-9

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

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

potassium methacrylate

107-07-3

2-chloro-ethanol

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

868-77-9

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

Conditions
ConditionsYield
With sulfuric acid
79-41-4

poly(methacrylic acid)

ethylene dioxide

ethylene dioxide

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
107-07-3

2-chloro-ethanol

potassium methacrylate

potassium methacrylate

868-77-9

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

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

ethylene glycol

920-46-7

Methacryloyl chloride

868-77-9

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

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

10H-phenothiazine

79-41-4

poly(methacrylic acid)

A

868-77-9

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

B

2351-43-1

2-(2-hydroxyethoxy)ethyl methacrylate

C

97-90-5

EDMA

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

oxirane

79-41-4

poly(methacrylic acid)

A

868-77-9

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

B

542-59-6

2-hydroxyethyl acetate

C

2351-43-1

2-(2-hydroxyethoxy)ethyl methacrylate

D

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

107-21-1

ethylene glycol

2421-28-5

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

868-77-9

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

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

oxirane

79-41-4

poly(methacrylic acid)

A

868-77-9

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

B

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
67-56-1

methanol

1279116-11-8

C26H59NO10P2Si4

A

868-77-9

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

B

1279116-04-9

C14H27NO10P2

C

6-hexanoic acid

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

methanol

1279116-12-9

C31H69NO10P2Si4

A

868-77-9

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

B

iminobis(methylenephosphono)undecanoic acid

C

1279116-05-0

C19H37NO10P2

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

C18H35NO10P2

A

868-77-9

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

B

6-hexanoic acid

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

C23H45NO10P2

A

868-77-9

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

B

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
20166-49-8

2-acetoxyethyl methylacrylate

868-77-9

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

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

868-77-9

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

B

C15H15NO7

Conditions
ConditionsYield
In tetrahydrofuran for 10h; Kinetics; UV-irradiation;
21282-97-3

2-(methacryloyloxy)ethyl acetoacetate

868-77-9

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

Conditions
ConditionsYield
With water at 90℃; for 54h; Reactivity;
21282-97-3

2-(methacryloyloxy)ethyl acetoacetate

A

868-77-9

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

B

67-64-1

acetone

Conditions
ConditionsYield
With water at 90℃; for 54h; Reactivity;
868-77-9

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

124-63-0

methanesulfonyl chloride

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
868-77-9

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

108-30-5

succinic acid anhydride

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%
868-77-9

2-methyl-2-propenoic acid 2-hydroxyethyl 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%
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  • Casno:

    868-77-9

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Reported in EPA TSCA Inventory.

Specification

The 2-Hydroxyethyl methacrylate, with its CAS registry number 868-77-9, has the IUPAC name of 2-hydroxyethyl 2-methylprop-2-enoate. For being a kind of colourless liquid, this is soluble in water and is sensitive to air. When comes to its production, it could be prepared by the reaction of ethylene oxide and methacrylic acid.

The characteristics of 2-Hydroxyethyl methacrylate are as follows:
 (1)ACD/LogP: 0.43; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.427; (4)ACD/LogD (pH 7.4): 0.427; (5)ACD/BCF (pH 5.5): 1.244; (6)ACD/BCF (pH 7.4): 1.244; (7)ACD/KOC (pH 5.5): 40.696; (8)ACD/KOC (pH 7.4): 40.696; (9)#H bond acceptors: 3; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 46.53; (13)Index of Refraction: 1.443; (14)Molar Refractivity: 32.724 cm3; (15)Molar Volume: 123.459 cm3; (16)Polarizability: 12.973×10-24 cm3; (17)Surface Tension: 33.723 dyne/cm; (18)Density: 1.054 g/cm3; (19)Flash Point: 97.222 °C; (20)Enthalpy of Vaporization: 49.49 kJ/mol; (21)Boiling Point: 189.031 °C at 760 mmHg; (22)Vapour Pressure: 0.159 mmHg at 25°C; (23)Exact Mass: 130.062994; (24)MonoIsotopic Mass: 130.062994; (25)Topological Polar Surface Area: 46.5; (26)Heavy Atom Count: 9; (27)Complexity: 118.

Production method of 2-Hydroxyethyl methacrylate:
oxirane could react with 2-methyl-acrylic acid to produce Ethylene glycol methacrylate. This reaction could happen in the presence of the reagent of Py, Cu(OAc)2.


Use of 2-Hydroxyethyl methacrylate:
Ethylene glycol methacrylate could react with isobutyryl chloride to produce 1-isobutyryloxy-2-methacryloyloxy-ethane. This reaction could happen in the presence of the reagent of pyridine.


Safety information of 2-Hydroxyethyl methacrylate:
When you are dealing with 2-Hydroxyethyl methacrylate, you should be very careful. This is irritating to eyes, respiratory system and skin and may cause inflammation to the skin or other mucous membranes. And it may cause sensitisation by skin contact. Therefore, you should wear suitable protective clothing and gloves. If in case of contact with eyes, rinse immediately with plenty of water and seek medical advice, and after contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer).

In addition, you could convert the following datas into the molecular structure:
(1)Canonical SMILES: CC(=C)C(=O)OCCO
(2)InChI: InChI=1S/C6H10O3/c1-5(2)6(8)9-4-3-7/h7H,1,3-4H2,2H3
(3)InChIKey: WOBHKFSMXKNTIM-UHFFFAOYSA-N 

Below are the toxicity information of 2-Hydroxyethyl methacrylate:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LDLo intravenous 99200nL/kg (99200mL/kg)   Journal of Pharmaceutical Sciences. Vol. 63, Pg. 376, 1974.
 
guinea pig LD50 oral 4680mg/kg (4680mg/kg) BEHAVIORAL: COMA Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 54(9), Pg. 75, 1989.
mouse LD50 intraperitoneal 497mg/kg (497mg/kg)   Journal of Pharmaceutical Sciences. Vol. 62, Pg. 778, 1973.
 
mouse LD50 oral 3275mg/kg (3275mg/kg) BEHAVIORAL: COMA Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 54(9), Pg. 75, 1989.
rat LD50 intraperitoneal 1250mg/kg (1250mg/kg)   Archives des Maladies Professionnelles de Medecine du Travail et de Securite Sociale. Vol. 36, Pg. 58, 1975.
rat LD50 oral 5050mg/kg (5050mg/kg) BEHAVIORAL: COMA Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 54(9), Pg. 75, 1989.