2-Phenoxyethyl acrylate
[CAS 48145-04-6]

Identification

• Classification: Chemical reagent >> Organic reagent >> Ester >> Other ester compounds
• Name: 2-Phenoxyethyl acrylate
• Synonyms: Acrylic acid 2-phenoxyethyl ester
• Molecular Formula: C₁₁H₁₂O₃
• Molecular Weight: 192.21
• CAS Registry Number: 48145-04-6
• EC Number: 256-360-6
• SMILES: C=CC(=O)OCCOC1=CC=CC=C1

Properties

• Density: 1.104
• Boiling point: 84 °C
• Refractive index: 1.518
• Flash point: 113 °C

Safety Data

• Hazard Symbols: GHS07;GHS08;GHS09 Warning
• Risk Statements: H315-H317-H319-H335-H361-H361d-H411
• Safety Statements: P203-P261-P264-P264+P265-P271-P272-P273-P280-P302+P352-P304+P340-P305+P351+P338-P318-P319-P321-P332+P317-P333+P317-P337+P317-P362+P364-P391-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Eye irritation	Eye Irrit.	2	H319
Skin sensitization	Skin Sens.	1	H317
Skin irritation	Skin Irrit.	2	H315
Skin sensitization	Skin Sens.	1A	H317
Reproductive toxicity	Repr.	2	H361
Specific target organ toxicity - single exposure	STOT SE	3	H335
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413
Respiratory sensitization	Resp. Sens.	1	H334
Reproductive toxicity	Repr.	2	H361d
Acute toxicity	Acute Tox.	4	H312

Discovery and Applications

2-Phenoxyethyl acrylate is a chemical compound with notable applications in polymer chemistry and materials science. Characterized by its functional acrylate group and phenoxyethyl moiety, this compound plays a crucial role in the development of advanced polymers and coatings with enhanced properties.

The discovery of 2-Phenoxyethyl acrylate stemmed from research focused on designing new acrylate esters with improved performance characteristics. The introduction of the phenoxyethyl group was aimed at modifying the physical and chemical properties of the acrylate ester to create polymers with specific functionalities. The compound's synthesis involves the esterification of phenoxyethanol with acrylic acid, resulting in a product with a dual functional group that provides a balance of reactivity and stability.

In polymer chemistry, 2-Phenoxyethyl acrylate is used as a monomer in the production of various types of polymers and copolymers. Its acrylate functionality allows for polymerization through free radical mechanisms, making it suitable for use in a range of polymerization processes. The resulting polymers often exhibit desirable properties such as high adhesion, flexibility, and chemical resistance.

One of the primary applications of 2-Phenoxyethyl acrylate is in the formulation of advanced coatings. These coatings are used in a variety of industries, including automotive, aerospace, and industrial sectors. The inclusion of 2-Phenoxyethyl acrylate in coating formulations enhances the durability and performance of the coatings, providing resistance to wear, abrasion, and environmental factors. This makes the coatings suitable for use in demanding applications where long-lasting protection is required.

Additionally, 2-Phenoxyethyl acrylate is utilized in the production of adhesives and sealants. Its adhesion properties make it effective in creating strong bonds between various substrates, including metals, plastics, and glass. This application is particularly valuable in industries where high-performance adhesives are needed for structural and industrial applications.

In the field of medical devices and materials, 2-Phenoxyethyl acrylate is used in the development of biocompatible polymers. Its ability to form flexible and durable films makes it suitable for applications in medical coatings and drug delivery systems. The compound's compatibility with biological systems and its non-toxic nature contribute to its suitability for use in medical and pharmaceutical applications.

Overall, 2-Phenoxyethyl acrylate is a versatile chemical compound with significant applications in coatings, adhesives, and medical materials. Its functional groups and polymerization characteristics make it a valuable component in the creation of advanced materials with improved performance and durability.

References

1984 Polymer and Formulation Design Characteristics for Developing Bonding Capabilities of Radiation-Curable Coatings and Adhesive Systems. Adhesive Chemistry.
DOI: 10.1007/978-1-4613-2435-5_19

2008 Properties and influence of hydrophobically associating polyacrylamide modified with 2-phenoxylethylacrylate. Frontiers of Materials Science in China, 2(1).
DOI: 10.1007/s11706-008-0020-x

2021 Allergic contact dermatitis from a disposable blood pressure cuff containing isobornyl acrylate and 2‐phenoxyethyl acrylate. Contact Dermatitis, 84(4).
DOI: 10.1111/cod.13761