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292818 Aldrich

2-Hydroxyethyl acrylate

96%, contains 200-650 ppm monomethyl ether hydroquinone as inhibitor

Synonym: Ethylene glycol monoacrylate

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Properties

Related Categories Acrylate, Acrylic Monomers, Building Blocks, C2 to C5, Carbonyl Compounds,
vapor density   >1 (vs air)
vapor pressure   <0.1 mmHg ( 20 °C)
assay   96%
contains   200-650 ppm monomethyl ether hydroquinone as inhibitor
refractive index   n20/D 1.45(lit.)
bp   90-92 °C/12 mmHg(lit.)
density   1.011 g/mL at 25 °C(lit.)
storage temp.   2-8°C

Description

Packaging

1 L in glass bottle

18 L in comp drum

250 mL in glass bottle

Application

Porous hydrogels can be prepared by copolymerization of 2-hydroxyethyl acrylate and a cross linking agent.1 2-hydroxyethyl acrylate may be used in the synthesis of amphilic block copolymers by nitroxide mediated living radical polymeration.2 Also, it may be used to prepare tuned poly(hydroxyethyl acrylate) by atom transfer radical polymerization.3

General description

2-Hydroxyethyl acrylate is a hydroxyl group containing vinyl monomer.

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4-Hydroxybutyl acrylate

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Hydroxypropyl acrylate, mixture of isomers

contains 200 ppm hydroquinone monomethyl ether as inhibitor, 95%

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Hazard Codes (Europe) 
T,N
Risk Statements (Europe) 
Safety Statements (Europe) 
26-36/39-45-61
RIDADR 
UN 2922 8/PG 2
WGK Germany 
2
Flash Point(F) 
213.8 °F
Flash Point(C) 
101 °C

Protocols & Articles

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Keywords: Organic synthesis, Polymer science, Polymerization reactions, Purification, Solvents

Peer-Reviewed Papers

References

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1. Porous poly (2-hydroxyethyl acrylate) hydrogels. Monleón Pradas M, et al. Polymer 42(10), 4667-4674, (2001)

2. Nitroxide-Mediated Copolymerization of 2-Hydroxyethyl Acrylate and 2-Hydroxypropyl Acrylate: Copolymerization Kinetics and Thermoresponsive Properties Hoogenboom R, et al. Macromol. Rapid Commun. 30(23), 2042-2048, (2009)

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3. Atom transfer radical polymerization of tert-butyl acrylate and preparation of block copolymers. Davis KA and Matyjaszewski K Macromolecules 33(11), 4039-4047, (2000)

Dose resolution optimization of polymer gel dosimeters using different monomers. Lepag M, Jayasakera PM, Bäck SA, et al. Phys. Med. Biol. 46(10), 2665-80, (2001)

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Altering peptide fibrillization by polymer conjugation. Dehn S, Castelletto V, Hamley IW, et al. Biomacromolecules 13(9), 2739-47, (2012)

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Contact dermatitis from acrylics in a histology laboratory assistant. Molina L, Amado A, Mattei PL, et al. Dermatitis 20(5), E11-2, (2009)

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Three-dimensional nanocomposite scaffolds with ordered cylindrical orthogonal pores. Rodríguez Hernández JC, Serrano Aroca A, Gómez Ribelles JL, et al. J. Biomed. Mater. Res. B. Appl. Biomater. 84(2), 541-9, (2008)

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Amphiphilic conetworks as regenerative controlled releasing antimicrobial coatings. Tiller JC, Sprich C, and Hartmann L J. Control. Release 103(2), 355-67, (2005)

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Electrochemical biosensing using amplification-by-polymerization. Wu Y, Liu S, and He L Anal. Chem. 81(16), 7015-21, (2009)

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Designing temperature-responsive biocompatible copolymers and hydrogels based on 2-hydroxyethyl(meth)acrylates. Khutoryanskaya OV, Mayeva ZA, Mun GA, et al. Biomacromolecules 9(12), 3353-61, (2008)

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Polymeric nanogels produced via inverse microemulsion polymerization as potential gene and antisense delivery agents. McAllister K, Sazani P, Adam M, et al. J. Am. Chem. Soc. 124(51), 15198-207, (2002)

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Systematic comparison of HEA and HEMA as initiators in enzymatic ring-opening polymerizations. Xiao Y, Takwa M, Hult K, et al. Macromol. Biosci. 9(7), 713-20, (2009)

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Synthesis, properties and controlled release behaviors of hydrogel networks using cyclodextrin as pendant groups. Liu YY and Fan XD Biomaterials 26(32), 6367-74, (2005)

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The effect of hydrogen bonding on intramolecular chain transfer in polymerization of acrylates. Liang K and Hutchinson RA Macromol. Rapid Commun. 32(14), 1090-5, (2011)

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Comparison of subchronic neurotoxicity of 2-hydroxyethyl acrylate and acrylamide in rats. Moser VC, Anthony DC, Sette WF, et al. Fundam. Appl. Toxicol. 18(3), 343-52, (1992)

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Synthesis and characterization of water-soluble silsesquioxane-based nanoparticles by hydrolytic condensation of triethoxysilane derived from 2-hydroxyethyl acrylate. Mori H, Miyamura Y, and Endo T Langmuir 23(17), 9014-23, (2007)

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Continuous (1)H AND (13)C signal enhancement in NMR spectroscopy and MRI using parahydrogen and hollow-fiber membranes. Roth M, Kindervater P, Raich HP, et al. Angew. Chem. Int. Ed. Engl. 49(45), 8358-62, (2010)

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Self-supporting hydrogel stamps for the microcontact printing of proteins. Coq N, van Bommel T, Hikmet RA, et al. Langmuir 23(9), 5154-60, (2007)

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Hydroxamic acid-containing hydrogels for nonabsorbed iron chelation therapy: synthesis, characterization, and biological evaluation. Polomoscanik SC, Cannon CP, Neenan TX, et al. Biomacromolecules 6(6), 2946-53, (2005)

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Quantitative evaluation of adhesive properties and drug-adhesive interactions for transdermal drug delivery formulations using linear solvation energy relationships. Li J, Masso JJ, and Rendon S J. Control. Release 82(1), 1-16, (2002)

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Structure and properties of methacrylate-endcapped caprolactone networks with modulated water uptake for biomedical applications. Ivirico JL, Martínez EC, Sánchez MS, et al. J. Biomed. Mater. Res. B. Appl. Biomater. 83(1), 266-75, (2007)

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Surface photo-grafting of polyurethane with 2-hydroxyethyl acrylate for promotion of human endothelial cell adhesion and growth. Guan J, Gao C, Feng L, et al. J. Biomater. Sci. Polym. Ed. 11(5), 523-36, (2000)

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Dielectric relaxation spectrum of poly (epsilon-caprolactone) networks hydrophilized by copolymerization with 2-hydroxyethyl acrylate. Sabater i Serra R, Escobar Ivirico JL, Meseguer Dueñas JM, et al. Eur. Phys. J. E 22(4), 293-302, (2007)

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Immobilization of yeast cells with polymeric carrier cross-linked using radiation technique. Zhaoxin L, Fengxia L, Bie Xiaomei B, et al. J. Agric. Food Chem. 50(10), 2798-801, (2002)

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Contact activation of plasmatic coagulation on polymeric membranes measured by the activity of kallikrein in heparinized plasma. Groth T, Synowitz J, Malsch G, et al. J. Biomater. Sci. Polym. Ed. 8(10), 797-807, (1997)

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In vitro drug release studies of 2-hydroxyethyl acrylate or 2-hydroxypropyl methacrylate-4-{(1E,4E)-5-[4-(acryloyloxy)phenyl]-3-oxopenta-1,4-dienyl}phenyl acrylate copolymer beads. Arun A and Reddy BS J. Biomed. Mater. Res. B. Appl. Biomater. 73(2), 291-300, (2005)

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Polymeric drug based on sulfanilamide: synthesis, antimicrobial and drug releasing studies. Umamaheswara Reddy C, Arun A, Amalraj A, et al. J. Pharm. Pharmacol. 59(9), 1207-13, (2007)

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The potential dermal irritating effect of residual (meth)acrylic monomers in pressure sensitive adhesive tapes. Tokumura F, Matsui T, Suzuki Y, et al. Drug Chem. Toxicol. 33(1), 1-7, (2010)

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Beil. 2,IV,1469

Corp MSDS 1 (1), 1921:B / FT-IR 2 (1), 1090:A / FT-NMR 1 (1), 1044:A / RegBook 1 (1), 753:J / Structure Index 1, 116:B:8 / Vapor Phase 3, 720:B

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