Description

Glycidyl Acrylate (CAS 106-90-1) is a highly reactive bifunctional monomer featuring both an epoxide group and an acrylate group, making it an invaluable compound for advanced polymer synthesis and modification. With the molecular formula C₆H₈O₃ and IUPAC name oxiran-2-ylmethyl prop-2-enoate, this clear to pale yellow liquid is widely utilized in the production of specialty resins, adhesives, coatings, and photopolymers. Its dual functionality allows for cross-linking via radical polymerization (acrylate group) and ring-opening reactions (epoxide group), enabling tailored material properties such as enhanced adhesion, chemical resistance, and mechanical strength. Glycidyl acrylate is stored under inert conditions to prevent premature polymerization and is typically stabilized with inhibitors like hydroquinone or MEHQ. Suitable for research and industrial applications, it is handled with care due to its irritant properties and sensitivity to light and heat.

Properties

• CAS Number: 106-90-1
• Complexity: 130
• IUPAC Name: oxiran-2-ylmethyl prop-2-enoate
• InChI: InChI=1S/C6H8O3/c1-2-6(7)9-4-5-3-8-5/h2,5H,1,3-4H2
• InChI Key: RPQRDASANLAFCM-UHFFFAOYSA-N
• Exact Mass: 128.047344113
• Molecular Formula: C6H8O3
• Molecular Weight: 128.13
• SMILES: C=CC(=O)OCC1CO1
• Topological: 38.8
• Monoisotopic Mass: 128.047344113
• Physical Description: Glycidyl acrylate is a light amber liquid.
• Color/Form: Liquid
• Boiling Point: 135 °F at 2 mmHg
• Melting Point: Freezing point: -41.5 °C
• Flash Point: 141 °F
• Solubility: 10 to 50 mg/mL at 68.9 °F
• Density: 1.1 – Denser than water; will sink
• Vapor Density: 4.4 – Heavier than air; will sink
• Vapor Pressure: 2.97 [mmHg]
• Autoignition Temperature: 415 °C
• Synonyms: GLYCIDYL ACRYLATE, 106-90-1, 2,3-Epoxypropyl acrylate, Glycidyl propenate, oxiran-2-ylmethyl prop-2-enoate, Acrylic acid glycidyl ester, 2-Propenoic acid, oxiranylmethyl ester, Acrylic acid, 2,3-epoxypropyl ester, 1-Propanol, 2,3-epoxy-, acrylate, glycidyl propenoate, Methacyclic acid, 2,3-epoxypropyl ester, NSC 24151, Glycidylester kyseliny akrylove, M 581, CCRIS 2625, HSDB 5376, EINECS 203-440-3, UNII-L8N627D5ZC, epoxypropyl acrylate, Glycidylester kyseliny akrylove [Czech], BRN 0109092, L8N627D5ZC, 2-Propenoic acid, 2-oxiranylmethyl ester, NSC-24151, NSC-67196, 2,3-Epoxypropanol acrylate, DTXSID5025360, GLYCIDYL ACRYLATE [HSDB], 2,3-EPOXY-PROPYLACRYLATE, 4-17-00-01005 (Beilstein Handbook Reference), Glycidylester kyseliny akrylove (Czech), 2,3Epoxypropyl acrylate, DTXCID905360, (+-)-GLYCIDYL ACRYLATE, 1Propanol, 2,3epoxy, acrylate, 2,3-EPA, (.+-.)-GLYCIDYL ACRYLATE, Acrylic acid, 2,3epoxypropyl ester, GLYCIDYL ACRYLATE, (+-)-, 2Propenoic acid, oxiranylmethyl ester, 2-PROPENOIC ACID, OXIRANYL METHYL ESTER, 2-PROPENOIC ACID, OXIRANYL METHYL ESTER (ACI), rpqrdasanlafcm-uhfffaoysa-n, oxiran-2-ylmethyl acrylate, Glycidyl Acrylate (stabilized with MEHQ), WLN: T3OTJ B1OV1U1, 1-Propanol,3-epoxy-, acrylate, Acrylic acid,3-epoxypropyl ester, Methacyclic acid,3-epoxypropyl ester, 2-Oxiranylmethyl acrylate, MFCD00005138, oxiran-2-ylmethylacrylate, 2-Oxiranylmethyl acrylate #, acrylic acid gly-cidyl ester, SCHEMBL17692, AAA10690, NSC24151, NSC67196, OM0320, GLYCIDYL ACRYLATE, (+/-)-, AKOS006282816, BS-26055, DB-040716, G0497, NS00020725, D78471, Q26841212

Application

Glycidyl acrylate is extensively used in the formulation of UV-curable coatings, inks, and adhesives, where its acrylate group enables rapid curing under UV light. It serves as a key modifier in epoxy resins, improving flexibility and reactivity for composite materials and electronic encapsulants. Additionally, it is employed in the synthesis of functionalized polymers for biomedical applications, such as drug delivery systems and tissue engineering scaffolds.

Safety and Hazards

GHS Hazard Statements

• H226: Flammable liquid and vapor [Warning Flammable liquids]
• H301: Toxic if swallowed [Danger Acute toxicity, oral]
• H311: Toxic in contact with skin [Danger Acute toxicity, dermal]
• H317: May cause an allergic skin reaction [Warning Sensitization, Skin]
• H318: Causes serious eye damage [Danger Serious eye damage/eye irritation]

Precautionary Statements

• P210, P233, P240, P241, P242, P243, P261, P262, P264, P264+P265, P270, P272, P280, P301+P316, P302+P352, P303+P361+P353, P305+P354+P338, P316, P317, P321, P330, P333+P317, P361+P364, P362+P364, P370+P378, P403+P235, P405, and P501

Hazard Classes and Categories

• Acute toxicity – category 3
• Acute toxicity – category 3
• Skin corrosion – category 1B
• Skin sensitisation – category 1
• Eye damage – category 1
• Acute toxicity – category 3
• Specific target organ toxicity – category 3
• Germ cell mutagenicity – category 2
• Carcinogenicity – category 1B
• Reproductive toxicity – category 1B
• Specific target organ toxicity – category 1

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