2370-63-0

Basic information

• Product Name: 2-ETHOXYETHYL METHACRYLATE
• Synonyms: 2-Ethoxyethyl methacrylate contains 100 ppm hydroquinone monomethyl ether as inhibitor, 99%;METHACRYLIC ACID 2-ETHOXYETHYL ESTER;ETHYLENE GLYCOL MONOETHYL ETHER METHACRYLATE;2-ETHOXYETHYL METHACRYLATE;2-Ethoxyethyl 2-methylacrylate;2-methyl-2-propenoicaci2-ethoxyethylester;2-Propenoic acid, 2-methyl-, 2-ethoxyethyl ester;2-Propenoicacid,2-methyl-,2-ethoxyethylester
• CAS NO: 2370-63-0
• Molecular Formula: C8H14O3
• Molecular Weight: 158.19
• EINECS: 219-135-3
• Product Categories: Acrylic Monomers;C8 to C9Monomers;Carbonyl Compounds;Esters;Methacrylate
• Mol File: 2370-63-0.mol
• Article Data: 2

Chemical Properties

• Melting Point: <25 °C
• Boiling Point: 91-93 °C35 mm Hg(lit.)
• Flash Point: 161 °F
• Appearance: /
• Density: 0.964 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.812mmHg at 25°C
• Refractive Index: n20/D 1.429(lit.)
• Storage Temp.: 2-8°C
• Solubility: 13g/l
• Water Solubility: 17.05g/L at 20℃
• Stability: Light Sensitive
• CAS DataBase Reference: 2-ETHOXYETHYL METHACRYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-ETHOXYETHYL METHACRYLATE(2370-63-0)
• EPA Substance Registry System: 2-ETHOXYETHYL METHACRYLATE(2370-63-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-27-36/37/39
• WGK Germany: 2
• Hazardous Substances Data: 2370-63-0(Hazardous Substances Data)

Usage

Flammability and Explosibility

Nonflammable

Purification Methods

Purify the ester as described under methyl methacrylate. [Beilstein 2 III 1291.]

InChI:InChI=1/C8H14O3/c1-4-10-5-6-11-8(9)7(2)3/h2,4-6H2,1,3H3

Synthetic route

2-ethoxy-ethanol (110-80-5) + Methacryloyl chloride (920-46-7) → 2-ethoxyethyl methacrylate (2370-63-0)

Conditions	Yield
With pyridine In diethyl ether at 35℃; for 4h;	77%

2-hydroxy-2-methylpropanenitrile (75-86-5) → 2-ethoxyethyl methacrylate (2370-63-0)

Conditions	Yield
With sulfur trioxide; copper at 80 - 130℃; Zufuegen von Wasser, Kochen und folgendes Erhitzen des Reaktionsgemisches mit Aethylenglykol-monoaethylaether auf 100-110grad;

2-ethoxy-ethanol (110-80-5) + methacrylic acid methyl ester (80-62-6) → 2-ethoxyethyl methacrylate (2370-63-0)

Conditions	Yield
With sulfuric acid
With sodium 2-ethoxyethoxide
With sodium 2-ethoxyethoxide

2-ethoxy-ethanol (110-80-5) + 1,2-propanediene (463-49-0) + carbon monoxide (201230-82-2) → 2-ethoxyethyl methacrylate (2370-63-0)

Conditions	Yield
dodecacarbonyl-triangulo-triruthenium at 100℃; under 11400 Torr; for 3h;	80 % Chromat.

methyl 2-methoxy-2-methylpropanoate (17860-39-8) → 2-ethoxyethyl methacrylate (2370-63-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: anhydrous oxalic acid; hydroquinone 2: H2SO4 View Scheme

2-ethoxyethyl methacrylate (2370-63-0) + 2-(naphthalen-1-yl)benzenamine (92855-12-4) → 2-ethoxyethyl 2-((1-(2-aminophenyl)naphthalen-2-yl)methyl)acrylate

Conditions	Yield
With disodium hydrogenphosphate; (S)-STRIP; palladium diacetate; silver sulfate In toluene at 60℃; for 48h; Schlenk technique; stereoselective reaction;	61%

2-ethoxyethyl methacrylate (2370-63-0) + buta-1,3-diene (106-99-0) → (Z)-2-Non-8-enyl-undeca-2,10-dienoic acid 2-ethoxy-ethyl ester

Conditions	Yield
With bis(acetylacetonate)nickel(II) In toluene

2-ethoxyethyl methacrylate (2370-63-0) + buta-1,3-diene (106-99-0) → (2E,5E)-2-Methyl-undeca-2,5,10-trienoic acid 2-ethoxy-ethyl ester

Conditions	Yield
With bis(acetylacetonate)nickel(II) In toluene

2-ethoxyethyl methacrylate (2370-63-0) + EDMA (97-90-5) + methacrylic acid methyl ester (80-62-6) → polymers (I)-(x)

Conditions	Yield
With potassium peroxomonosulphate; sodium dodecyl-sulfate In cyclohexane; water at 60 - 70℃; for 3.5h; Product distribution; different ratios of monomers and solvent;

2,6-diphenyl-4-[4-(2-methylacryloyloxy)-phenyl]-pyrylium tetrafluoroborate + 2-ethoxyethyl methacrylate (2370-63-0) → polymer, radical copolymerization; monomer(s): 4-[4-(2-methyl-acryloyloxy)-phenyl]-2,6-diphenyl-pyranylium tetrafluoroborate; 2-ethoxyethyl methacrylate, molar ratio 0.5:100

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); EDMA at 65℃; for 5h;

2,6-diphenyl-4-[4-(2-methylacryloyloxy)-phenyl]-pyrylium tetrafluoroborate + 2-ethoxyethyl methacrylate (2370-63-0) → polymer, radical copolymerization; monomer(s): 4-[4-(2-methyl-acryloyloxy)-phenyl]-2,6-diphenyl-pyranylium tetrafluoroborate; 2-ethoxyethyl methacrylate, molar ratio 1.0:100

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); EDMA at 65℃; for 5h;

2,6-diphenyl-4-[4-(2-methylacryloyloxy)-phenyl]-pyrylium tetrafluoroborate + 2-ethoxyethyl methacrylate (2370-63-0) → polymer, radical copolymerization; monomer(s): 4-[4-(2-methyl-acryloyloxy)-phenyl]-2,6-diphenyl-pyranylium tetrafluoroborate; 2-ethoxyethyl methacrylate, molar ratio 2.0:100

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); EDMA at 65℃; for 5h;

2,6-diphenyl-4-[4-(2-methylacryloyloxy)-phenyl]-pyrylium tetrafluoroborate + 2-ethoxyethyl methacrylate (2370-63-0) + 2,3-dihydroxypropyl methacrylate (5919-74-4) → polymer, radical copolymerization; monomer(s): 4-[4-(2-methyl-acryloyloxy)-phenyl]-2,6-diphenyl-pyranylium tetrafluoroborate; 2-ethoxyethyl methacrylate; 2,3-dihydroxypropyl methacrylate, molar ratio 0.5:75:25

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); EDMA at 65℃; for 5h;

2,6-diphenyl-4-[4-(2-methylacryloyloxy)-phenyl]-pyrylium tetrafluoroborate + 2-ethoxyethyl methacrylate (2370-63-0) + 2,3-dihydroxypropyl methacrylate (5919-74-4) → polymer, radical copolymerization; monomer(s): 4-[4-(2-methyl-acryloyloxy)-phenyl]-2,6-diphenyl-pyranylium tetrafluoroborate; 2-ethoxyethyl methacrylate; 2,3-dihydroxypropyl methacrylate, molar ratio 1.0:75:25

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); EDMA at 65℃; for 5h;

2,6-diphenyl-4-[4-(2-methylacryloyloxy)-phenyl]-pyrylium tetrafluoroborate + 2-ethoxyethyl methacrylate (2370-63-0) + 2,3-dihydroxypropyl methacrylate (5919-74-4) → polymer, radical copolymerization; monomer(s): 4-[4-(2-methyl-acryloyloxy)-phenyl]-2,6-diphenyl-pyranylium tetrafluoroborate; 2-ethoxyethyl methacrylate; 2,3-dihydroxypropyl methacrylate, molar ratio 2.0:75:25

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); EDMA at 65℃; for 5h;

2,6-diphenyl-4-[4-(2-methylacryloyloxy)-phenyl]-pyrylium tetrafluoroborate + 2-ethoxyethyl methacrylate (2370-63-0) + 2,3-dihydroxypropyl methacrylate (5919-74-4) → polymer, radical copolymerization; monomer(s): 4-[4-(2-methyl-acryloyloxy)-phenyl]-2,6-diphenyl-pyranylium tetrafluoroborate; 2-ethoxyethyl methacrylate; 2,3-dihydroxypropyl methacrylate, molar ratio 0.5:50:50

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); EDMA at 65℃; for 5h;

2,6-diphenyl-4-[4-(2-methylacryloyloxy)-phenyl]-pyrylium tetrafluoroborate + 2-ethoxyethyl methacrylate (2370-63-0) + 2,3-dihydroxypropyl methacrylate (5919-74-4) → polymer, radical copolymerization; monomer(s): 4-[4-(2-methyl-acryloyloxy)-phenyl]-2,6-diphenyl-pyranylium tetrafluoroborate; 2-ethoxyethyl methacrylate; 2,3-dihydroxypropyl methacrylate, molar ratio 1.0:50;50

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); EDMA at 65℃; for 5h;

2,6-diphenyl-4-[4-(2-methylacryloyloxy)-phenyl]-pyrylium tetrafluoroborate + 2-ethoxyethyl methacrylate (2370-63-0) + 2,3-dihydroxypropyl methacrylate (5919-74-4) → polymer, radical copolymerization; monomer(s): 4-[4-(2-methyl-acryloyloxy)-phenyl]-2,6-diphenyl-pyranylium tetrafluoroborate; 2-ethoxyethyl methacrylate; 2,3-dihydroxypropyl methacrylate, molar ratio 2.0:50:50

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); EDMA at 65℃; for 5h;

N-(2-hydroxyethyl)methacrylamide (5238-56-2) + 2-ethoxyethyl methacrylate (2370-63-0) + EDMA (97-90-5) → polymer; monomer(s): 2-ethoxyethyl methacrylate, 90 mol percent; 1,2-ethanediol dimethacrylate; 2-hydroxyethyl methacrylamide

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) at 70℃; for 5h;

N-(2-hydroxyethyl)methacrylamide (5238-56-2) + 2-ethoxyethyl methacrylate (2370-63-0) + EDMA (97-90-5) → polymer; monomer(s): 2-ethoxyethyl methacrylate, 80 mol percent; 1,2-ethanediol dimethacrylate; 2-hydroxyethyl methacrylamide

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) at 70℃; for 5h;

N-(2-hydroxyethyl)methacrylamide (5238-56-2) + 2-ethoxyethyl methacrylate (2370-63-0) + EDMA (97-90-5) → polymer; monomer(s): 2-ethoxyethyl methacrylate, 70 mol percent; 1,2-ethanediol dimethacrylate; 2-hydroxyethyl methacrylamide

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) at 70℃; for 5h;

N-(2-hydroxyethyl)methacrylamide (5238-56-2) + 2-ethoxyethyl methacrylate (2370-63-0) + EDMA (97-90-5) → polymer; monomer(s): 2-ethoxyethyl methacrylate, 60 mol percent; 1,2-ethanediol dimethacrylate; 2-hydroxyethyl methacrylamide

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) at 70℃; for 5h;

N-(2-hydroxyethyl)methacrylamide (5238-56-2) + 2-ethoxyethyl methacrylate (2370-63-0) + EDMA (97-90-5) → polymer; monomer(s): 2-ethoxyethyl methacrylate, 50 mol percent; 1,2-ethanediol dimethacrylate; 2-hydroxyethyl methacrylamide

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) at 70℃; for 5h;

2-ethoxyethyl methacrylate (2370-63-0) + EDMA (97-90-5) → polymer; monomer(s): 2-ethoxyethyl methacrylate; 1,2-ethanediol dimethacrylate

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) at 70℃; for 5h;

2-ethoxyethyl methacrylate (2370-63-0) → polymer; monomer(s): 2-ethoxyethyl methacrylate

Conditions	Yield
With 2,2-dimethoxy-2-phenylacetophenone at 25℃; UV-irradiation;

2,6-diphenyl-4-[4-(2-methylacryloyloxy)-phenyl]-pyrylium tetrafluoroborate + 2-ethoxyethyl methacrylate (2370-63-0) + EDMA (97-90-5) + 2,3-dihydroxypropyl methacrylate (5919-74-4) → polymer, product of radical copolymerization; monomer(s): 2,6-diphenyl-4-[4-(2-methylacryloyloxy)-phenyl]-pyrylium tetrafluoroborate; 2-ethoxyethyl methacrylate; 2,3-dihydroxypropyl methacrylate; ethyleneglycol dimethacrylate

Conditions	Yield
With 2,2'-azobis(isobutyronitrile)

2,6-bis(4-methylphenyl)-4-[4-(2-methylacryloyloxy)-phenyl]-pyrylium tetrafluoroborate + 2-ethoxyethyl methacrylate (2370-63-0) + EDMA (97-90-5) + 2,3-dihydroxypropyl methacrylate (5919-74-4) → polymer, product of radical copolymerization; monomer(s): 2,6-bis(4-methylphenyl)-4-[4-(2-methylacryloyloxy)-phenyl]-pyrylium tetrafluoroborate; 2-ethoxyethyl methacrylate; 2,3-dihydroxypropyl methacrylate; ethyleneglycol dimethacrylate

Conditions	Yield
With 2,2'-azobis(isobutyronitrile)

2,6-bis(4-methoxyphenyl)-4-[4-(2-methylacryloyloxy)-phenyl]-pyrylium tetrafluoroborate + 2-ethoxyethyl methacrylate (2370-63-0) + EDMA (97-90-5) + 2,3-dihydroxypropyl methacrylate (5919-74-4) → polymer; monomer(s): 2,6-bis(4-metoxyphenyl)-4-[4-(2-methylacryloyloxy)-phenyl]-pyrylium tetrafluoroborate; 2-ethoxyethyl methacrylate; 2,3-dihydroxypropyl methacrylate; ethyleneglycol dimethacrylate

Conditions	Yield
With 2,2'-azobis(isobutyronitrile)

Upstream product

• 110-80-5 2-ethoxy-ethanol 
• 920-46-7 Methacryloyl chloride 
• 17860-39-8 methyl 2-methoxy-2-methylpropanoate 
• 463-49-0 1,2-propanediene 
• 201230-82-2 carbon monoxide 
• 80-62-6 methacrylic acid methyl ester 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 

Relevant articles and documents

Ruthenium-catalyzed carbonylation of allene: Direct synthesis of methacrylates and methacrylamides

Carbonylation reactions of allene in alcohols and amines in the presence of a ruthenium carbonyl catalyst under mild conditions gave methacrylates and methacrylamides, respectively, in good yields with an atom economy of 100%.