2-[2-(2-Methoxyethoxy)ethoxy]ethyl methacrylate

• CAS: 24493-59-2
• Catalog Number: ACM24493592-2
• Category: Main Products
• Molecular Weight: 232.27g/mol
• Molecular Formula: C11H20O5
• Synonyms: Methoxytriethyleneglycol methacrylate;; Triethylene glycol methyl ether methacrylate
• IUPAC Name: 2-[2-(2-methoxyethoxy)ethoxy]ethyl 2-methylprop-2-enoate
• SMILES: CC(=C)C(=O)OCCOCCOCCOC
• InChI: InChI=1S/C11H20O5/c1-10(2)11(12)16-9-8-15-7-6-14-5-4-13-3/h1,4-9H2,2-3H3
• InChI Key: OBBZSGOPJQSCNY-UHFFFAOYSA-N
• Appearance: Clear colorless to pale yellow liquid
• Complexity: 203
• Covalently-Bonded Unit Count: 1
• EC Number: 246-288-3
• Exact Mass: 232.131074g/mol
• Formal Charge: 0
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Heavy Atom Count: 16
• Monoisotopic Mass: 232.131074g/mol
• Rotatable Bond Count: 11
• XLogP3: 0.7

Case Study

2-[2-(2-Methoxyethoxy)ethoxy]ethyl Methacrylate as Thermo-Responsive Monomer for PMEO2MA Hydrogel Hydration Studies

Olejniczak, Magdalena N., et al. Journal of Raman Spectroscopy 48.3 (2017): 465-473.

2-[2-(2-Methoxyethoxy)ethoxy]ethyl methacrylate (MEO2MA) acts as the main monomer for constructing thermo-responsive poly(MEO2MA) hydrogels whose network architecture governs water-polymer interactions, informing the design of volume phase transition materials for biomedical use.
Experimental Protocol: MEO2MA, 2-hydroxyethyl methacrylate and ethylene glycol dimethacrylate mixtures (molar ratio 100:2:1) are irradiated in ampoules with 6 MeV electron pulses to a total dose of 50 kGy, producing irregular free-radical networks; these are compared with regular networks obtained by atom transfer radical polymerization, both bare and decorated with grafted dangling chains, plus a linear analogue; fully swollen gels are analyzed by Raman spectroscopy during isothermal drying (500-4000 cm^-1, 4 cm^-1 resolution) with density functional theory calculations and thermo-optical analysis at 2 degrees Celsius per minute.
Performance Evaluation: Total bound water is independent of topology at about 11 water molecules per polymer unit, and only about 40% of carbonyl groups are hydrated even at equilibrium swelling. Network architecture strongly affects complex stability: dehydration of carbonyl groups begins below 2, 4 and 5 water molecules per unit for regular bare, irregular and decorated networks respectively, correlating with volume phase transition temperatures of 36.3, 21.7 and 16.2 degrees Celsius. Computed binding energies (-33.6, -31.5 and -27.7 kJ/mol) confirm carbonyl groups form the strongest hydrogen bonds, establishing hydration as the key determinant of thermo-responsiveness.

2-[2-(2-Methoxyethoxy)ethoxy]ethyl Methacrylate as Thermo-Responsive Comonomer for Smart Comfort Control of Textiles

Chen, Yangyi, et al. Textile Research Journal 87.13 (2017): 1620-1630.

2-[2-(2-Methoxyethoxy)ethoxy]ethyl methacrylate (MEO2MA) serves as the thermo-responsive comonomer in a random copolymer whose reversible collapse above its transition temperature switches surface morphology from compact to porous, enabling smart control of cotton fabric comfort.
Experimental Protocol: A random copolymer of MEO2MA and ethylene glycol methacrylate (molar ratio 17:3) is synthesized by atom transfer radical polymerization, and cotton poplin (180 g/m²) is cross-linked with the polymer using citric acid from solutions of 2, 4, 8 or 16 wt%, followed by curing at 130 degrees Celsius; air permeability (100 Pa pressure drop), water vapor transmission, equilibrium swelling ratio, softness, whiteness, washing and abrasion fastness are evaluated at 25 and 45 degrees Celsius.
Performance Evaluation: The water vapor transmission ratio (45 to 25 degrees Celsius) rises from 3.0 for pristine cotton to 3.5 after modification, and the equilibrium swelling ratio drops sharply from 108.4% to 102.6% across the roughly 37 degree Celsius transition; at 16 wt% the swelling difference reaches 34.6%. Softness is preserved (curve area 0.101 versus 0.554 for a poly(N-isopropylacrylamide) coating), whiteness and breaking stress remain near 78.3% and 57 MPa, and over 84% of the coating survives five washes, confirming durable, comfortable smart textiles.

2-[2-(2-Methoxyethoxy)ethoxy]ethyl Methacrylate as Thermo-Responsive Monomer for Radiation-Synthesized Gradient Hydrogels

Kadlubowski, Slawomir, et al. Radiation Physics and Chemistry 100 (2014): 23-31.

2-[2-(2-Methoxyethoxy)ethoxy]ethyl methacrylate (MEO2MA) serves as the thermo-responsive monomer whose radiation-induced free radical polymerization and cross-linking yields hydrogels with a gradient in cross-link density, providing one-step synthesis of transient materials for biomedical applications.
Experimental Protocol: Air-saturated monomer mixtures of MEO2MA, 2-hydroxyethyl methacrylate and ethylene glycol dimethacrylate (molar ratios 100:2:1 or 100:5:1) are irradiated in 2 mL ampoules with 6 MeV electron pulses (5.3 Gy per pulse, dose rate 10⁷ Gy/s) to doses of 27.5-100 kGy; gels are conditioned for 24 hours at 7, 25 or 50 degrees Celsius, then equilibrated in water at 7 degrees Celsius for at least 3 weeks before gravimetric swelling, scanning electron microscopy, Raman and solid-state NMR analysis.
Performance Evaluation: The gelation dose drops from 50.4 kGy for neat MEO2MA to about 27 kGy with 1% cross-linker, with negligible chain scission (p0/q0 = 0). Low doses produce a gradient material whose bottom section swells about four times less than the upper, hydrophilic section (contact angles 99 versus 68 degrees) yet is chemically identical, and equilibrium swelling below the roughly 15 degree Celsius transition is strongly temperature-dependent, confirming tunable gradient hydrogels for tissue scaffolds and drug delivery.

Custom Q&A

What is the molecular formula of 2-[2-(2-Methoxyethoxy)ethoxy]ethyl methacrylate?

The molecular formula is C11H20O5.

What is the molecular weight of 2-[2-(2-Methoxyethoxy)ethoxy]ethyl methacrylate?

The molecular weight is 232.27 g/mol.

What is the IUPAC name of 2-[2-(2-Methoxyethoxy)ethoxy]ethyl methacrylate?

The IUPAC name is 2-[2-(2-methoxyethoxy)ethoxy]ethyl 2-methylprop-2-enoate.

What is the InChI of 2-[2-(2-Methoxyethoxy)ethoxy]ethyl methacrylate?

The InChI is InChI=1S/C11H20O5/c1-10(2)11(12)16-9-8-15-7-6-14-5-4-13-3/h1,4-9H2,2-3H3.

What is the InChIKey of 2-[2-(2-Methoxyethoxy)ethoxy]ethyl methacrylate?

The InChIKey is OBBZSGOPJQSCNY-UHFFFAOYSA-N.

What is the canonical SMILES of 2-[2-(2-Methoxyethoxy)ethoxy]ethyl methacrylate?

The canonical SMILES is CC(=C)C(=O)OCCOCCOCCOC.

What is the CAS number of 2-[2-(2-Methoxyethoxy)ethoxy]ethyl methacrylate?

The CAS number is 24493-59-2.

What is the XLogP3 value of 2-[2-(2-Methoxyethoxy)ethoxy]ethyl methacrylate?

The XLogP3 value is 0.7.

How many hydrogen bond acceptor count does 2-[2-(2-Methoxyethoxy)ethoxy]ethyl methacrylate have?

It has 5 hydrogen bond acceptor count.

How many rotatable bond count does 2-[2-(2-Methoxyethoxy)ethoxy]ethyl methacrylate have?

It has 11 rotatable bond count.