ChemicalBook > CAS DataBase List > 2-Hydroxyethyl methacrylate

2-Hydroxyethyl methacrylate

Product Name
2-Hydroxyethyl methacrylate
CAS No.
868-77-9
Chemical Name
2-Hydroxyethyl methacrylate
Synonyms
HEMA;GMA;HYDROXYETHYL METHACRYLATE;GLYCOL METHACRYLATE;ETHYLENE GLYCOL METHACRYLATE;BisoMer HEMA;N5-Methyl-L-glutamine;Hydroxyethyl Methacrylat;2-(Methacryloyloxy)ethanol;Hydroxyethyl methacrylate (HEMA)
CBNumber
CB4690827
Molecular Formula
C6H10O3
Formula Weight
130.14
MOL File
868-77-9.mol
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2-Hydroxyethyl methacrylate Property

Melting point:
-12 °C
Boiling point:
67 °C3.5 mm Hg(lit.)
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.)
Flash point:
207 °F
storage temp. 
2-8°C
solubility 
Chloroform, Methanol (Slightly)
form 
Liquid
pka
13.83±0.10(Predicted)
color 
Clear
Odor
Ester like
Water Solubility 
soluble
FreezingPoint 
-20
FreezingPoint 
-96
Sensitive 
Air Sensitive
BRN 
1071583
Stability:
Unstable - may polymerize in the absence of stabilizer. May be stabilized with, or contain small amounts of, diethylene glycol monomethacrylate, di(ethylene glycol)dimethacrylate, methacrylic acid. Incompatible with strong oxidizing agents, free radical initiators, peroxides, steel. Closed containers may explode if heated due to runaway polymer
InChIKey
WOBHKFSMXKNTIM-UHFFFAOYSA-N
LogP
0.42 at 25℃
CAS DataBase Reference
868-77-9(CAS DataBase Reference)
NIST Chemistry Reference
2-Hydroxyethyl methacrylate(868-77-9)
EPA Substance Registry System
2-Hydroxyethyl methacrylate (868-77-9)
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Safety

Hazard Codes 
Xi
Risk Statements 
36/38-43-36/37/38
Safety Statements 
26-36/37-28A-28
WGK Germany 
1
RTECS 
OZ4725000
TSCA 
Yes
HS Code 
29161490
Hazardous Substances Data
868-77-9(Hazardous Substances Data)
Toxicity
LD50 orally in Rabbit: 5050 mg/kg LD50 dermal Rabbit > 3000 mg/kg
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H317May cause an allergic skin reaction

H319Causes serious eye irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P272Contaminated work clothing should not be allowed out of the workplace.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
8.00588
Product name
2-Hydroxyethyl methacrylate
Purity
(stabilised with hydroquinone monomethyl ether) for synthesis
Packaging
250ML
Price
$60.3
Updated
2024/03/01
Sigma-Aldrich
Product number
8.00588
Product name
2-Hydroxyethyl methacrylate
Purity
(stabilised with hydroquinone monomethyl ether) for synthesis
Packaging
2.5L
Price
$132
Updated
2024/03/01
Sigma-Aldrich
Product number
17348
Product name
2-Hydroxyethyl methacrylate
Purity
embedding medium (for microscopy)
Packaging
250ML
Price
$115
Updated
2024/03/01
Sigma-Aldrich
Product number
128635
Product name
2-Hydroxyethyl methacrylate
Purity
contains ≤250 ppm monomethyl ether hydroquinone as inhibitor, 97%
Packaging
1kg
Price
$52
Updated
2024/03/01
Sigma-Aldrich
Product number
128635
Product name
2-Hydroxyethyl methacrylate
Purity
contains ≤250 ppm monomethyl ether hydroquinone as inhibitor, 97%
Packaging
18kg
Price
$547
Updated
2024/03/01
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2-Hydroxyethyl methacrylate Chemical Properties,Usage,Production

Chemical Properties

colourless liquid

Uses

2-Hydroxyethyl methacrylate is the methacrylic monomer for use in UV inks, adhesives, lacquers, dental materials, artificial nails, etc.

Uses

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.

Uses

2-Hydroxyethyl methacrylate is used for preparation of hydrophilic polymers for biomedical devices.

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.

Environmental Fate

2-Hydroxyethyl methacrylate's production and use in acrylic resins, enamels, and as a binder for non-woven fabrics may result in its release to the environment through various waste streams. If released into the air, a vapor pressure of 0.126 mm Hg at 25 °C indicates that 2-hydroxyethyl methacrylate will exist solely as a vapor in the ambient atmosphere. Vapor-phase 2-hydroxyethyl methacrylate will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 16 hours. If released to soil, 2-hydroxyethyl methacrylate is expected to have very high mobility based upon an estimated Koc of 43. Volatilization from moist soil surfaces is not expected to be an important fate process based upon an estimated Henry's Law constant of 4.6X10-9 atm-cu m/mole. 2-Hydroxyethyl methacrylate is not expected to volatilize from dry soil surfaces based on its vapor pressure. If released into water, 2-hydroxyethyl methacrylate is not expected to adsorb to suspended solids and sediment in the water column based on the estimated Koc. 2-Hydroxyethyl methacrylate reached 92-100% of its theoretical BOD in 2 weeks using an activated sludge inoculum. Volatilization from water surfaces is not expected to be a necessary fate process based on this compound's estimated Henry's Law constant. An estimated BCF of 1.3 suggests the potential for bioconcentration in aquatic organisms is low. Hydrolysis of 2-hydroxyethyl methacrylate may be a significant process under basic conditions based upon a hydrolytic half-life of 4 hours at pH 11 for the structurally similar butyl acrylate; half-lives for butyl acrylate at pH 7, 8, and 9 were 4 years, 150 days, and 15 days, respectively. Occupational exposure to 2-hydroxyethyl methacrylate may occur through inhalation and dermal contact with this compound at workplaces where 2-hydroxyethyl methacrylate is produced or used. The general population may be exposed to 2-hydroxyethyl methacrylate via inhalation or dermal contact with acrylic resins or enamels containing this compound.

Metabolism

2-hydroxyethyl methacrylate (HEMA) is a monomer based on methacrylic acid (MAA) used to produce biomaterials such as dental adhesive and composite resins. The process of polymerization, which is run in situ, is always incomplete, resulting in the presence of free monomers in the oral cavity. Moreover, monomers can be released from polymer-based tooth restorations through mechanical shearing and enzymatic degradation of polymers. They may penetrate the pulp through microchannels in the dentin structure. HEMA, like many of MAA-based monomers, is an ester, so it can be targeted by esterases when in organism and can undergo degradation. The main product of HEMA hydrolysis is MAA, which may undergo further degradation producing several intermediates of potential biological activity[1].

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.]

Toxics Screening Level

The ITSL can be determined from the mouse LD50 from Tanii and Hashimoto using the equation from R232(1)(h) as follows.
ITSL = (5887 mg/kg)/( 500x 40 x 100 x 0.167) x 1kg/1.7m3 = 10 μg/m3 annual average.
The default mouse inhalation rate of 1.7 m3/kg was used in the above calculation.

2-Hydroxyethyl methacrylate Preparation Products And Raw materials

Raw materials

ETHYLENE OXIDE Polymerization inhibitor 2-Chloroethanol Hydroquinone Tetramethylammonium chloride Methacrylic acid

Preparation Products

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2-Hydroxyethyl methacrylate Suppliers

Americas 1 Australia 1 Belgium 4 Canada 3 CHINA 476 Europe 2 France 1 Germany 11 India 38 Italy 1 Japan 15 Singapore 2 Slovakia 1 South Korea 1 Spain 1 Switzerland 2 The Netherlands 2 United Arab Emirates 1 United Kingdom 13 United States 57 USA 1 Global 634
Esstech Inc.
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View Lastest Price from 2-Hydroxyethyl methacrylate manufacturers

HEBEI SHENGSUAN CHEMICAL INDUSTRY CO.,LTD
Product
2-Hydroxyethyl methacrylate 868-77-9
Price
US $999.00-666.00/ton
Min. Order
1ton
Purity
99%
Supply Ability
5000
Release date
2024-08-20
HEBEI SHENGSUAN CHEMICAL INDUSTRY CO.,LTD
Product
2-Hydroxyethyl methacrylate 868-77-9
Price
US $99.00-66.00/kg
Min. Order
0.0010000000474974513kg
Purity
99%
Supply Ability
5000
Release date
2024-08-19
Yancheng Green Chemicals Co.,Ltd
Product
2-Hydroxyethyl methacrylate，HEMA 868-77-9
Price
US $0.00/KG
Min. Order
200KG
Purity
98
Supply Ability
10mt
Release date
2020-12-28

868-77-9, 2-Hydroxyethyl methacrylateRelated Search:

Methyl acrylate Ethyl acrylate Ethylene glycol Ethylene glycol diacetate Ethylene carbonate Diethylene glycol ETHYLENE OXIDE ETHYLENE Butyl methacrylate Ethyl 2-hydroxybenzoate 2-(METHYLSULFONYL)ETHANOL Triethylene glycol Ethyl methacrylate 2-Hydroxyethyl acrylate 2-Butoxyethanol ETHYL 2-CYANOACRYLATE ETHYLENE DIACRYLATE 2-Hydroxypropyl methacrylate Ethylene Glycol Methacrylate

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  • BleMMer E
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  • MhoroMer BM 903
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  • 2-Hydroxyethyl Methacrylate, stabilized, 97% 1KG
  • 2-Hydroxyethyl Methacrylate, stabilized, 97% 25GR
  • 2-Hydroxyethyl Methacrylate, stabilized, 97% 500GR
  • 2-Hydroxyethyl methacrylate, stabilized, 96%
  • METHANESULFOMIC ACID
  • 2-Hydroxyethyl Methacrylate, Stabilized with 250 ppM MEHQ
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  • 2-Hydroxyethyl Methacrylate >=99%, contains <=50 ppM MonoMethyl ether hydroquinone as inhibitor
  • 2-Hydroxyethyl methacrylate( 99%,HyDry, stabilized with 100ppm MEHQ,Water≤50 ppm (by K.F.))
  • 2-Hydroxyethyl methacrylate( 99%,HyDry, with molecular sieves, stabilized with 100ppm MEHQ,Water≤50 ppm (by K.F.))
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