2-hydroxyethyl 2-methylprop-2-enoate

• ChemBase ID: 131584
• Molecular Formular: C6H10O3
• Molecular Mass: 130.1418
• Monoisotopic Mass: 130.06299418
• SMILES: CC(=C)C(=O)OCCO
• Canonical SMILES: CC(=C)C(=O)OCCO
• InChI: InChI=1S/C6H10O3/c1-5(2)6(8)9-4-3-7/h7H,1,3-4H2,2H3
• InChIKey: WOBHKFSMXKNTIM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-hydroxyethyl 2-methylprop-2-enoate
• IUPAC Traditional name: HEMA
• Synonyms: HEMA; 2-Hydroxyethyl methacrylate; 1,2-Ethanediol mono(2-methylpropenoate); Glycol methacrylate; 2-hydroxyethyl 2-methylprop-2-enoate; 2-Methyl-2-propenoic Acid 2-Hydroxyethyl Ester; 2-(Methacryloyloxy)ethanol; Acryester HISS; Acryester HO; Bisomer HEMA; Bisomer SR; Blemmer E; EB 109; Ethylene Glycol Methacrylate; Ethylene Glycol Monomethacrylate; GE 610; Glycol Monomethacrylate; HEMA 90; Light Ester HO; Light Ester HO 250; Mhoromer BM 903; Mhoromer BM 905; Monomer MG 1; NSC 24180; Rocryl 400; β-Hydroxyethyl Methacrylate; 2-Hydroxyethyl Methacrylate; Methacrylic acid 2-hydroxyethyl ester; 乙二醇单甲基丙烯酸酯; 甲基丙烯酸2-羟乙酯; 2-羟基乙基甲基丙烯酸酯; 2-羟基乙基 甲基丙烯酸盐

Database IDs

• CAS Number: 868-77-9
• EC Number: 212-782-2
• MDL Number: MFCD00002863
• Beilstein Number: 1071583
• PubChem SID: 24850449; 24871325; 162225862; 24874485; 24847870
• PubChem CID: 13360

CALCULATED PROPERTIES

• Acid pKa: 15.095923
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 0.61762315
• LogD (pH = 7.4): 0.61762315
• Log P: 0.61762315
• Molar Refractivity: 32.7099 cm^3
• Polarizability: 12.963648 Å^3
• Polar Surface Area: 46.53 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Pale Yellow Oil
• Melting Point: -12°C
• Boiling Point: 250°C; 67 °C/3.5 mmHg(lit.)
• Flash Point: 101 °C; 101°C(213°F); 204.8 °F; 214 °F; 96 °C
• Density: 1.071; 1.071 g/mL at 20 °C; 1.073 g/mL at 25 °C(lit.)
• Refractive Index: 1.4530; n20/D 1.453; n20/D 1.453(lit.)
• Vapor Pressure: 0.01 mmHg ( 25 °C)
• Vapor Density: 5 (vs air)
• Hydrophobicity(logP): 0.303

Safety Information

• Storage Condition: Amber Vial, -20°C Freezer
• Storage Warning: Air Sensitive
• RTECS: OZ4725000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 1; 3
• Risk Statements: 36/37/38-43; 36/38-43
• Safety Statements: 26-28; 26-36/37
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H317-H319; H315-H317-H319-H335; H315-H319-H317
• GHS Precautionary statements: P261-P280-P305 + P351 + P338; P261-P280-P305+P351+P338-P302+P352-P321-P501A; P280-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95% (GC); ≥97.0% (GC); ≥99%; ≥99.0% (GC); 95%; 97%; 97%, stab. with ca 500ppm 4-methoxyphenol; 98%
• Grade: embedding medium (for microscopy); puriss.; purum; technical
• Impurities: <250 mg/kg free acid (as methycrylic acid) (T)
• Contains: ~0.001% hydroquinone monomethyl ether as stabilizer; ~0.001% hydroquinone monomethylether as stabilizer; ≤50 ppm monomethyl ether hydroquinone as inhibitor; 200 ppm monomethyl ether hydroquinone as inhibitor; 200-220 ppm monomethyl ether hydroquinone as inhibitor; 300 ppm hydroquinone monomethyl ether as inhibitor; hydroquinone monomethyl ether as stabilizer
• Linear Formula: CH2=C(CH3)COOCH2CH2OH

DETAILS

Sigma Aldrich - 17348

Application
2-Hydroxyethyl methacrylate has been used in a study to describe a novel methodology for grafting polymers via radical photopolymerization initiated on gold surfaces by aryl layers from diazonium salt precursors. 2-Hydroxyethyl methacrylate has also been used in a study to provide insight into the induction of apoptosis and the differential expression of antioxidant enzymes depending on the availability of glutathione.

Sigma Aldrich - 525464

Packaging
100 mL in glass bottle

Sigma Aldrich - 477028

Application
A polymeric hydrogel for drug delivery.1
Packaging
25, 100 mL in poly bottle

Sigma Aldrich - 128635

Packaging
1 kg in poly bottle
5 g in glass bottle
18 kg in comp drum
500 g in poly bottle

Toronto Research Chemicals - H942230

Used for preparation of hydrophilic polymers for biomedical devices.

REFERENCES

• Delbressine, L., et al.: Xenobiotica, 11, 241 (1981)
• Gerberick, G., et al.: Toxicol. Sci., 97, 417 (1981)