6976-93-8

Basic information

• Product Name: 2-Methoxyethyl methacrylate
• Synonyms: ETHYLENE GLYCOL METHYL ETHER METHACRYLATE;2-METHOXYETHYL METHACRYLATE;2-methyl-2-propenoicaci2-methoxyethylester;2-Propenoicacid,2-methyl-,2-methoxyethylester;Ethylene glycol methyl ether methacrylate~Methacrylic acid 2-methoxyethyl ether;Methoxyethyl Methacrylate;Methacrylic acid (3-oxabutan-1-yl) ester;Methacrylic acid 2-methoxyethyl ester
• CAS NO: 6976-93-8
• Molecular Formula: C₇H₁₂O₃
• Molecular Weight: 144.17
• EINECS: 230-241-9
• Mol File: 6976-93-8.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 65 °C12 mm Hg(lit.)
• Flash Point: 150 °F
• Appearance: /
• Density: 0.993 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.22mmHg at 25°C
• Refractive Index: n20/D 1.431(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility: 31.33g/L at 20℃
• CAS DataBase Reference: 2-Methoxyethyl methacrylate(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methoxyethyl methacrylate(6976-93-8)
• EPA Substance Registry System: 2-Methoxyethyl methacrylate(6976-93-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-43
• Safety Statements: 26-36
• RIDADR: 2810
• WGK Germany: 3
• HazardClass: 6.1(a)
• PackingGroup: I
• Hazardous Substances Data: 6976-93-8(Hazardous Substances Data)

Usage

Uses

Used in the synthesis of copolymers of styrene and 2-methoxyethyl methacrylate.

General Description

Polymers prepared from this monomer may have uses in polyelectrolytes and may be biocompatible.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C7H12O3/c1-6(2)7(8)10-5-4-9-3/h1,4-5H2,2-3H3

Synthetic route

α-acetoxy-isobutyric acid-(2-methoxy-ethyl ester) → 2-methoxyethyl (meth)acrylate (6976-93-8)

Conditions	Yield
at 450℃;
at 450℃;

2-methoxy-ethanol (109-86-4) + methyl methacrylate (97-63-2) → 2-methoxyethyl (meth)acrylate (6976-93-8)

Conditions	Yield
at 60℃;

2-methoxy-ethanol (109-86-4) + methacrylic acid methyl ester (80-62-6) → 2-methoxyethyl (meth)acrylate (6976-93-8)

Conditions	Yield
With sulfuric acid; benzene
With sulfuric acid; benzene

2-methoxy-ethanol (109-86-4) + Methacryloyl chloride (920-46-7) → 2-methoxyethyl (meth)acrylate (6976-93-8)

Conditions	Yield
With triethylamine In benzene at 20℃;

α-hydroxy-isobutyric acid-(2-methoxy-ethyl ester) → 2-methoxyethyl (meth)acrylate (6976-93-8)

Conditions	Yield
Multi-step reaction with 2 steps 2: 450 °C View Scheme
Multi-step reaction with 2 steps 2: 450 °C View Scheme

styrene (292638-84-7) + 2-methoxyethyl (meth)acrylate (6976-93-8) → polymer, block copolymer, Mn 24000 by 1H NMR, Mw/Mn 1.05 by SEC; monomer(s): styrene; 2-methoxyethyl methacrylate

Conditions	Yield
Stage #1: styrene With sec.-butyllithium In tetrahydrofuran; n-heptane at -78℃; for 0.333333h; Stage #2: 2-methoxyethyl (meth)acrylate With 1,1-Diphenylethylene; diethylzinc In tetrahydrofuran; n-heptane at -78℃; for 3h;	100%

2-methoxyethyl (meth)acrylate (6976-93-8) → polymer, Mn 37000 by end-group analysis using 1H NMR, Mw/Mn 1.16 by SEC, triad tacticity mm 3 percent, mr 32 percent, rr 65 percent by 1H NMR; monomer(s): 2-methoxyethyl methacrylate

Conditions	Yield
With 1,1-Diphenylethylene; sec.-butyllithium In tetrahydrofuran; n-heptane at -78℃; for 2h;	100%

2-methoxyethyl (meth)acrylate (6976-93-8) → polymer, Mn 16000 by end-group analysis using 1H NMR, Mw/Mn 1.03 by SEC, triad tacticity mm 4 percent, mr 30 percent, rr 66 percent by 1H NMR; monomer(s): 2-methoxyethyl methacrylate

Conditions	Yield
With 1,1-Diphenylethylene; sec.-butyllithium; lithium chloride In tetrahydrofuran; n-heptane at -78℃; for 2h;	100%

2-methoxyethyl (meth)acrylate (6976-93-8) → polymer, Mn 12000 by end-group analysis using 1H NMR, Mw/Mn 1.28 by SEC, triad tacticity mm 17 percent, mr 52 percent, rr 31 percent by 1H NMR; monomer(s): 2-methoxyethyl methacrylate

Conditions	Yield
With (diphenylmethyl)potassium In tetrahydrofuran at -78℃; for 2h;	100%

2-methoxyethyl (meth)acrylate (6976-93-8) → polymer, Mn 14000 by end-group analysis using 1H NMR, Mw/Mn 1.04 by SEC, triad tacticity mm 13 percent, mr 52 percent, rr 35 percent by 1H NMR; monomer(s): 2-methoxyethyl methacrylate

Conditions	Yield
With diethylzinc; (diphenylmethyl)potassium In tetrahydrofuran at -78℃; for 2h;	100%

2-methoxyethyl (meth)acrylate (6976-93-8) + 2-(naphthalen-1-yl)benzenamine (92855-12-4) → 2-methoxyethyl 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;	75%

2-methoxyethyl (meth)acrylate (6976-93-8) + acrylic acid (79-10-7) → poly((acrylic acid)-co-(2-methoxyethyl methacrylate)) random copolymer, methacrylate content (NMR): 5 mol %, Mw (GPC): 3.6E5, Mw/Mn (GPC): 3.6; monomer(s): acrylic acid; 2-methoxyethyl methacrylate

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In benzene at 65℃; for 12h;

2-methoxyethyl (meth)acrylate (6976-93-8) + acrylic acid (79-10-7) → poly((acrylic acid)-co-(2-methoxyethyl methacrylate)) random copolymer, methacrylate content (NMR): 10 mol %, Mw (GPC): 3.7E5, Mw/Mn (GPC): 1.9; monomer(s): acrylic acid; 2-methoxyethyl methacrylate

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In benzene at 65℃; for 12h;

2-methoxyethyl (meth)acrylate (6976-93-8) + acrylic acid (79-10-7) → poly((acrylic acid)-co-(2-methoxyethyl methacrylate)) random copolymer, methacrylate content (NMR): 20 mol %, Mw (GPC): 2.2E5, Mw/Mn (GPC): 1.9; monomer(s): acrylic acid; 2-methoxyethyl methacrylate

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In benzene at 65℃; for 12h;

2-methoxyethyl (meth)acrylate (6976-93-8) + acrylic acid (79-10-7) → poly((acrylic acid)-co-(2-methoxyethyl methacrylate)) random copolymer, methacrylate content (NMR): 27 mol %, Mw (GPC): 2.6E5, Mw/Mn (GPC): 1.9; monomer(s): acrylic acid; 2-methoxyethyl methacrylate

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In benzene at 65℃; for 12h;

2-methoxyethyl (meth)acrylate (6976-93-8) + acrylic acid (79-10-7) → poly((acrylic acid)-co-(2-methoxyethyl methacrylate)) random copolymer, methacrylate content (NMR): 45 mol %, Mw (GPC): 3.1E5, Mw/Mn (GPC): 3.4; monomer(s): acrylic acid; 2-methoxyethyl methacrylate

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In benzene at 65℃; for 12h;

2-methoxyethyl (meth)acrylate (6976-93-8) + copper(II) bis(trifluoromethanesulfonate) (34946-82-2) → C75H114O24P(1+)*CF3O3S(1-)

Conditions	Yield
With triphenylphosphine In water at 20℃; for 4h; Temperature; Reagent/catalyst; Inert atmosphere; Glovebox;

2-methoxyethyl (meth)acrylate (6976-93-8) + 2-(naphthalen-1-yl)benzenamine (92855-12-4) → 2-methoxyethyl 2-((1-(2-aminophenyl)naphthalen-2-yl)methyl)acrylate

Conditions	Yield
With palladium diacetate; silver carbonate; N-acetylglycine In toluene at 60℃; for 24h; Schlenk technique;

Upstream product

• 109-86-4 2-methoxy-ethanol 
• 920-46-7 Methacryloyl chloride 
• 80-62-6 methacrylic acid methyl ester 
• 97-63-2 methyl methacrylate 

Relevant articles and documents

Unique associative properties of copolymers of sodium acrylate and oligo(ethylene oxide) alkyl ether methacrylates in water

A series of random copolymers of sodium acrylate and oligo(ethylene oxide) alkyl ether methacrylates (CnEmMA) with different lengths of ethylene oxide (EO) and alkyl groups were prepared by free-radical copolymerization at varying copolymer compositions. The lengths of the EO units (the number of EO units) (m) and the numbers of carbon atoms in the alkyl groups (n) ranged fro'm 0 to 8.7 and 1 to 6, respectively. The copolymers with n = 1 and m = 1-8.7 exhibited a marked increase in solution viscosity at polymer concentrations (Cp) higher than their overlap concentrations (C*) when the CnEmMA contents (x) in the copolymers were in a certain limited range. Namely, there was an optimum x value that yielded the highest viscosity as a consequence of the competition between inter- and intrapolymer associations; the maximum viscosities occurred around x ≈ 25, 15, 10, 7, and 3 mol % for m = 1, 2, 3, 4.2, and 8.7, respectively. The maximum viscosity decreased significantly as n was increased on going from 1 to 6, and for the copolymers with n = 6, no increase in the viscosity occurred, a trend opposite to what is expected to interpolymer hydrophobic associations. When Cp > C*, steady-shear viscosity depended on the nature of countercations; the viscosities were found to be higher in the order Li + > Na+ ? NH4+, whereas reduced viscosity in dilute regime (Cp C*) was independent of the species of the cations. Rheological properties were found to be typical of transient networks formed through very weak interpolymer associations. Thus, the large increase in solution viscosity was explained by simultaneous interactions of countercations with EO units via coordination and with the polyanion via counterion condensation.