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Home> Encyclopedia >Ester & Derivatives>Pharmaceutical Intermediates>Organic Intermediate
Glycidyl methacrylate structure
Glycidyl methacrylate structure

Glycidyl methacrylate

Iupac Name:oxiran-2-ylmethyl 2-methylprop-2-enoate
CAS No.: 106-91-2
Molecular Weight:142.1525
Modify Date.: 2022-10-31 05:23
Introduction: Colorless liquid with a fruity odor. Floats on water. View more+
1. Names and Identifiers
1.1 Name
Glycidyl methacrylate
1.2 Synonyms

2-((Methacryloxy)methyl)oxirane 2,3-epoxypropyl methacrylate 2-Methyl-2-oxiranyl-2-propenoic acid Methyl ester blemmergma CP 105 cp105 EINECS 203-441-9 Glycidol methacrylate Glycidyl Methacrylate OR Methacrylic acid 2,3-epoxypropyl ester Glycidyl methacrylate(GMA) Methacrylic Acid Glycidyl Ester MFCD00005137 oxiran-2-ylmethyl methacrylate

1.3 CAS No.
106-91-2
1.4 CID
7837
1.5 EINECS(EC#)
203-441-9
1.6 Molecular Formula
C7H10O3 (isomer)
1.7 Inchi
InChI=1S/C7H10O3/c1-5(2)7(8)10-4-6-3-9-6/h6H,1,3-4H2,2H3
1.8 InChkey
VOZRXNHHFUQHIL-UHFFFAOYSA-N
1.9 Canonical Smiles
CC(=C)C(=O)OCC1CO1
1.10 Isomers Smiles
CC(=C)C(=O)OCC1CO1
2. Properties
2.1 Density
1.042
2.1 Melting point
-52oC
2.1 Boiling point
189℃
2.1 Refractive index
1.449-1.451
2.1 Flash Point
76℃
2.2 Precise Quality
142.06300
2.2 PSA
38.83000
2.2 logP
0.50450
2.2 Solubility
0.5-1.0 g/100 mL at 20 ºC
2.3 Viscosity
5.481 cP at 70 °F
2.4 VaporDensity
Relative vapor density (air = 1): 4.9
2.5 Appearance
Colorless liquid, fruity odor.
2.6 Storage
Ambient temperatures.
2.7 Chemical Properties
Glycidyl methacrylate (GMA) is a colorless liquid with a fruity odor. Floats on water. (USCG, 1999)
2.8 Color/Form
Colorless liquid
2.9 Decomposition
When heated to decomp it emits acrid smoke and fumes.
2.10 Odor
Fruity odor
2.11 Water Solubility
0.5-1.0 g/100 mL at 20 oC
2.12 Spectral Properties
Index of refraction: 1.448 @ 25 deg C/D
Index of refraction: 1.4494 at 20 deg C
2.13 Stability
Unstable. Light sensitive. May be stabilized with around 100ppmMEHQ. Refrigerate.
2.14 StorageTemp
2-8°C
2.15 Surface Tension
25 dynes/cm= 0.025 N/m at 20 °C (est)
3. Use and Manufacturing
3.1 General Description
Colorless liquid with a fruity odor. Floats on water.
3.2 Polymerization
Heat, peroxides, and caustics all cause polymerization.
3.3 Usage
Glycidyl methacrylate (GMA) is a common monomer used in the creation of epoxy resins. It is used to provide epoxy functionalization to polyolefins and other acrylate resins.Glycidyl methacrylate is used in the production of polymer coatings and finishes, adhesives, plastics and elastomers.Glycidyl methacrylate dextran has been reported to be used as a biocompatible hydrogel. In situ polymerization of GMA with trimethylolpropane trimethacrylate to form macroporous sorbents has also been reported. GMA may also be grafted onto polypropylene.
4. Safety and Handling
4.1 Symbol
GHS05, GHS06, GHS08
4.1 Hazard Codes
Xn
4.1 Signal Word
Danger
4.1 Risk Statements
R20/21/22;R36/38;R43
4.1 Safety Statements
S26;S28
4.1 Exposure Standards and Regulations
Homopolymers and copolymers of Glycidyl methacrylate are an indirect food additive for use only as a component of adhesives.
4.2 Packing Group
III
4.2 Fire Hazard
Special Hazards of Combustion Products: Irritating vapors are generated when heated Glycidyl methacrylate Preparation Products And Raw materials Raw materials
4.3 Other Preventative Measures
... Hazard is the generation of considerable exothermic heat in some of the reactions, so that high pressures & temp may develop. This danger ... should be borne in mind when designing plant. Awareness of the dangers and of good engineering design are essential to safety. Employees should be instructed about the necessity of cleansing the skin if it is contaminated by materials which are irritants or skin-absorbed. With careful design, however, and complete enclosure of those processes where toxic chemicals or intermediates occur, dangerous exposures can be avoided. /Acrylic acid & derivatives/
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.
4.4 Hazard Class
8
4.4 Hazard Declaration
H302 + H332-H311-H314-H317-H341-H350-H360F-H370
4.4 DisposalMethods
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
4.5 RIDADR
UN 2810
4.5 Caution Statement
P201-P260-P280-P305 + P351 + P338-P310
4.5 Formulations/Preparations
Grades or purity: Technical: 92%
Inhibitor of polymerization: Hydroquinone monomethyl ether: 50 ppm
4.6 WGK Germany
2
4.6 RTECS
OZ4375000
4.6 Protective Equipment and Clothing
SUITABLE PROTECTIVE CLOTHING & SELF-CONTAINED RESP PROTECTIVE APPARATUS SHOULD BE AVAILABLE FOR USE OF THOSE WHO MAY HAVE TO RESCUE PERSONS OVERCOME BY FUMES. /ACRYLIC ACID & DERIVATIVES/
Polyethylene-coated apron and gloves and close-fitting goggles.
4.7 Skin, Eye, and Respiratory Irritations
Irritating to eyes and skin.
4.8 Safety
Hazard Codes:Xn,T
Risk Statements:20/21/22-36/38-43-60-45
20/21/22:Harmful by inhalation, in contact with skin and if swallowed
36/38:Irritating to eyes and skin
43:May cause sensitization by skin contact
60:May impair fertility
45:May cause cancer
Safety Statements:26-28-28A-45-36/37-53
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
28:After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer)
45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
36/37:Wear suitable protective clothing and gloves
53:Avoid exposure - obtain special instruction before use
RIDADR:UN 2810 6.1/PG 3
WGK Germany:2
HazardClass:8
PackingGroup:III
HS Code:29161490
Hazardous Substances Data:106-91-2(Hazardous Substances Data)
4.9 Specification

The Glycidyl methacrylate, with the cas registry number 106-91-2, has the IUPAC name of oxiran-2-ylmethyl 2-methylprop-2-enoate. For being a kind of clear liquid with a fruity odor, it is slightly water soluble while insoluble in organics. This chemical is unstable chemically and it is sensitive to light. Besides, it belongs to the category of epoxides which is highly reactive, and they could polymerize in the presence of catalysts or when heated with the very violent reactions. What's more, its product categories are including Oxiranes; Simple 3-Membered Ring Compounds.

The physical properties of this chemical are below: (1)ACD/LogP: 0.34; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.342; (4)ACD/LogD (pH 7.4): 0.342; (5)ACD/BCF (pH 5.5): 1.072; (6)ACD/BCF (pH 7.4): 1.072; (7)ACD/KOC (pH 5.5): 36.572; (8)ACD/KOC (pH 7.4): 36.572; (9)#H bond acceptors: 3; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 38.83; (13)Index of Refraction: 1.458; (14)Molar Refractivity: 35.397 cm3; (15)Molar Volume: 129.752 cm3; (16)Polarizability: 14.032 ×10-24 cm3; (17)Surface Tension: 36.121 dyne/cm; (18)Density: 1.096 g/cm3; (19)Flash Point: 76.111 °C; (20)Enthalpy of Vaporization: 42.521 kJ/mol; (21)Boiling Point: 188.999 °C at 760 mmHg; (22)Vapour Pressure: 0.582 mmHg at 25°C; (23)Exact Mass: 142.062994; (24)MonoIsotopic Mass: 142.062994; (25)Topological Polar Surface Area: 38.8; (26)Heavy Atom Count: 10; (27)Formal Charge: 0; (28)Complexity: 162.

The production method of this chemical is below: It could be prepared by reaction of sodium methacrylate and epichlorohydrin, with the norm quota of consumption of the material: methacrylic acid 780kg/t, epoxy chloropropane 690kg/t and sodium hydroxide 330kg/t.

As to its usage, it is widely applied in many ways. It could be used as the powder coating like crylic acid painting and also as the thermoset coating; It could also be used as the fibre finishing agent, adhesive agent, antistatic agent, chloroethylene stabilizing agent, and also could be applied in pharmaceutics.  

When you are using this chemical, you should be very cautious. For one thing, it is a kind of harmful chemical which may cause damage to health. It is irritating to eyes and skin and may cause sensitisation by skin contact. If by inhalation, in contact with skin and if swallowed, it is dangerous to our body. For another thing, it is toxic which may at low levels cause damage to health. This chemical may cause impair fertility and even cause cancer.

Therefore, you could take the different measures to deal with different cases. The first important thing is to wear suitable protective clothing and gloves. If in case of contact with eyes, rinse immediately with plenty of water and seek medical advice; If in case of accident or if you feel unwell, seek medical advice immediately (show the label where possible); If contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer); And after using it, wash thoroughly after handling, and then rmove contaminated clothing and wash before reuse. Then remember to avoid exposure - obtain special instructions before use. When keeping this chemical, you should store it in a tightly closed container and in a cool dry area away from incompatible substances, and away from HEAT, sparks,flame and sources of ignition.

Additionally, you could convert the following datas into the molecular structure:
(1)Canonical SMILES: CC(=C)C(=O)OCC1CO1
(2)InChI: InChI=1S/C7H10O3/c1-5(2)7(8)10-4-6-3-9-6/h6H,1,3-4H2,2H3
(3)InChIKey: VOZRXNHHFUQHIL-UHFFFAOYSA-N 

Below are the toxicity information of this chemical:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LCLo inhalation 1400mg/m3/6H (1400mg/m3) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES National Technical Information Service. Vol. OTS0530684,
guinea pig LCLo inhalation 1400mg/m3/6H (1400mg/m3) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES National Technical Information Service. Vol. OTS0530684,
guinea pig LD50 oral 697mg/kg (697mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 50(2), Pg. 67, 1985.
mouse LD50 oral 390mg/kg (390mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 50(2), Pg. 67, 1985.
rabbit LCLo inhalation 1400mg/m3/6H (1400mg/m3) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES National Technical Information Service. Vol. OTS0530684,
rabbit LD50 skin 450uL/kg (0.45mL/kg)   American Industrial Hygiene Association Journal. Vol. 30, Pg. 470, 1969.
 
rat LC50 inhalation 45ppm/4H (45ppm) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

BLOOD: OTHER CHANGES
National Technical Information Service. Vol. OTS0546546,
rat LD50 oral 500mg/kg (500mg/kg)   Weisheng Dulixue Zazhi. Journal of Health Toxicology. Vol. 6, Pg. 91, 1992.

 

4.10 Toxicity
The liquid irritates eyes about as much as soap. Prolonged contact with skin produces irritation and dermatitis.
5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

Acute toxicity - Dermal, Category 4

Skin irritation, Category 2

Eye irritation, Category 2

Skin sensitization, Category 1

Acute toxicity - Inhalation, Category 4

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Warning

Hazard statement(s)

H302 Harmful if swallowed

H312 Harmful in contact with skin

H315 Causes skin irritation

H319 Causes serious eye irritation

H317 May cause an allergic skin reaction

H332 Harmful if inhaled

Precautionary statement(s)
Prevention

P264 Wash ... thoroughly after handling.

P270 Do not eat, drink or smoke when using this product.

P280 Wear protective gloves/protective clothing/eye protection/face protection.

P261 Avoid breathing dust/fume/gas/mist/vapours/spray.

P272 Contaminated work clothing should not be allowed out of the workplace.

P271 Use only outdoors or in a well-ventilated area.

Response

P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell.

P330 Rinse mouth.

P302+P352 IF ON SKIN: Wash with plenty of water/...

P312 Call a POISON CENTER/doctor/\u2026if you feel unwell.

P321 Specific treatment (see ... on this label).

P362+P364 Take off contaminated clothing and wash it before reuse.

P332+P313 If skin irritation occurs: Get medical advice/attention.

P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.

P337+P313 If eye irritation persists: Get medical advice/attention.

P333+P313 If skin irritation or rash occurs: Get medical advice/attention.

P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing.

Storage

none

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

7. Other Information
7.0 BRN
2506
7.1 Chemical Properties
Glycidyl methacrylate (GMA) is a colorless liquid with a fruity odor. Floats on water. (USCG, 1999)
Glycidyl methacrylate
Glycidyl methacrylate is a polyfunctional monomer. It acts as an adhesion promoting crosslinking co-monomer for acrylic and vinyl resins. It is also a reactive colorless diluent. GMA is soluble in ethanol, acetone, diethyl ether, benzene.
7.2 Uses
Glycidyl methacrylate (GMA) is a common monomer used in the creation of epoxy resins. It is used to provide epoxy functionalization to polyolefins and other acrylate resins.
Glycidyl methacrylate is used in the production of polymer coatings and finishes, adhesives, plastics and elastomers.
Glycidyl methacrylate dextran has been reported to be used as a biocompatible hydrogel. In situ polymerization of GMA with trimethylolpropane trimethacrylate to form macroporous sorbents has also been reported. GMA may also be grafted onto polypropylene.
7.3 Uses
Glycidyl methacrylate dextran (GMA) has been reported to be used as a biocompatible hydrogel. In situ polymerization of GMA with trimethylolpropane trimethacrylate to form macroporous sorbents has also been reported. GMA may also be grafted onto polypropylene.
7.4 Usage
Glycidyl methacrylate is commonly used as a monomer for the preparation of epoxy resins. It is also used to provide epoxy functionalization to polyolefins and other acrylate resins. Further, it is also useful as an epoxy resin additive for paint coating formulations and adhesive applications.
8. Computational chemical data
  • Molecular Weight: 142.1525g/mol
  • Molecular Formula: C7H10O3
  • Compound Is Canonicalized: True
  • XLogP3-AA: 0.8
  • Exact Mass: 142.062994177
  • Monoisotopic Mass: 142.062994177
  • Complexity: 162
  • Rotatable Bond Count: 4
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Topological Polar Surface Area: 38.8
  • Heavy Atom Count: 10
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count: 1
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 1
  • CACTVS Substructure Key Fingerprint: AAADccBgMAAAAAAAAAAAAAAAEgAAAAAAAAAAAAAAAAAAAAAAAAAAGgAAAAAADBSggAICCAAABACIAgDSCAAAAAAAAAAAAAEAAEABBAAAIQACAAABAAACIIAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==
9. Question & Answer
  • Glycidyl methacrylate (GMA) is an ester of methacrylic acid and glycidol. It is a common monomer used in the production of epoxy resins. GMA is also a high purity, dual functionality monomer ideally suited for coating and resin applications. The Glycidyl Methacrylate market has been expanding at a ...
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11. Realated Product Infomation