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106-91-2

Basic Information
CAS No.: 106-91-2
Name: Glycidyl methacrylate
Article Data: 35
Cas Database
Molecular Structure:
Molecular Structure of 106-91-2 (Glycidyl methacrylate)
Formula: C7H10O3
Molecular Weight: 142.155
Synonyms: 2-Propenoicacid, 2-methyl-, oxiranylmethyl ester (9CI);Methacrylic acid, 2,3-epoxypropylester (6CI,7CI,8CI);2,3-Epoxypropyl methacrylate;2-Methylacrylicacid oxiranylmethyl ester;2-[(Methacryloyloxy)methyl]oxirane;3-Methacryloyloxy-1,2-epoxypropane;Acryester G;Blemmer G;Blemmer GH-LC;Blemmer GMA;Blemmer GP;Blemmer GS;Epoxypropyl methacrylate;Glycidolmethacrylate;Glycidyl a-methylacrylate;Light Ester G;Methacryloyloxymethyloxirane;NSC 24156;NSC 67195;SR 379;SY-Monomer G;Sartomer 379;Sartomer SR 379;
EINECS: 203-441-9
Density: 1.042 g/cm3
Melting Point: -52 °C
Boiling Point: 188.999 °C at 760 mmHg
Flash Point: 76.111 °C
Solubility: water: 0.5-1.0 g/100 mL at 20 °C
Appearance: clear liquid
Hazard Symbols: HarmfulXn,ToxicT
Risk Codes: 20/21/22-36/38-43-60-45
Safety: 26-28-28A-45-36/37-53
Transport Information: UN 2810 6.1/PG 3
PSA: 38.83000
LogP: 0.50450
Synthetic route
556-52-5

oxiranyl-methanol

106-89-8

epichlorohydrin

106-91-2

2,3-Epoxypropyl methacrylate

Conditions
ConditionsYield
With chlorine93%
With chlorine91.3%
66794-22-7

epoxychloropropane

79-41-4

poly(methacrylic acid)

106-91-2

2,3-Epoxypropyl methacrylate

Conditions
ConditionsYield
Stage #1: epoxychloropropane With 10H-phenothiazine; sodium carbonate In dichloromethane at 70℃; for 1h; Large scale;
Stage #2: poly(methacrylic acid) With tetrabutyl ammonium fluoride In dichloromethane; water at 102℃; for 3.5h; Large scale;
90%
sodium carbonate anhydride

sodium carbonate anhydride

79-41-4

poly(methacrylic acid)

150-76-5

4-methoxy-phenol

106-89-8

epichlorohydrin

106-91-2

2,3-Epoxypropyl methacrylate

Conditions
ConditionsYield
tetramethlyammonium chloride In water87.8%
79-41-4

poly(methacrylic acid)

106-89-8

epichlorohydrin

106-91-2

2,3-Epoxypropyl methacrylate

Conditions
ConditionsYield
Stage #1: poly(methacrylic acid) With sodium hydroxide In methanol at 20℃; for 0.5h;
Stage #2: epichlorohydrin In methanol at 35℃;
60%
With N-phenyl-1-naphthylamine; benzyltrimethylammonium chloride
With 2,2'-dihydroxy-5,5'-dimethyl-3,3'-di-tert-burtyl-1,1'-diphenylmethane; sodium carbonate; tetrabutyl-ammonium chloride for 1.83333h; Product distribution / selectivity; Heating / reflux;
96-05-9

allyl methacrylate

A

106-91-2

2,3-Epoxypropyl methacrylate

B

140914-83-6

2-Methyl-oxirane-2-carboxylic acid allyl ester

Conditions
ConditionsYield
With sodium hydroxide; sodium tungstate; dihydrogen peroxide; Aliquat 336 In dichloromethane; phosphoric acid at 25℃; for 208h; Yields of byproduct given;A 50%
B n/a
With sodium hydroxide; sodium tungstate; dihydrogen peroxide; Aliquat 336 In dichloromethane; phosphoric acid at 40℃; for 30h; Product distribution; variation in reaction conditions;A 50%
B 4%
With sodium hydroxide; sodium tungstate; dihydrogen peroxide; Aliquat 336 In dichloromethane; phosphoric acid at 25℃; for 160h;A 46.5%
B 4%
556-52-5

oxiranyl-methanol

920-46-7

Methacryloyl chloride

106-91-2

2,3-Epoxypropyl methacrylate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 4h; Inert atmosphere; Schlenk technique; Glovebox;35%
With pyridine; benzene
556-52-5

oxiranyl-methanol

80-62-6

methacrylic acid methyl ester

106-91-2

2,3-Epoxypropyl methacrylate

Conditions
ConditionsYield
With potassium cyanide; 2,4-dimethyl-6-tert-butylphenol at 70 - 80℃; for 2h; Green chemistry;25.3%
13818-44-5

(2-oxo-1,3-dioxolane-4-yl)methyl methacrylate

106-91-2

2,3-Epoxypropyl methacrylate

Conditions
ConditionsYield
1-methyl-3-(n-butyl)imidazolium iodide Product distribution / selectivity;8.6%
79-41-4

poly(methacrylic acid)

106-89-8

epichlorohydrin

A

106-91-2

2,3-Epoxypropyl methacrylate

B

109573-57-1

2-Methyl-acrylic acid 2-chloro-1-hydroxymethyl-ethyl ester

Conditions
ConditionsYield
With potassium carbonate; 1.) Sn-P 1.) benzene, reflux, 20 h; 2.) acetone, reflux, 6 h; Yield given. Multistep reaction;
865-48-5

sodium t-butanolate

(+-)-methacrylic acid-<3-chloro-2-hydroxy-propyl ester>

(+-)-methacrylic acid-<3-chloro-2-hydroxy-propyl ester>

106-91-2

2,3-Epoxypropyl methacrylate

Conditions
ConditionsYield
With diethyl ether; tert-butyl alcohol
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  • Casno:

    106-91-2

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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.