2-Methyl-2-propenoic acid 2-oxo-2-[2,2,2-trifluoro-1-(trifluoromethyl)ethoxy]ethyl ester
[CAS# 1176273-30-5]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: 2-Methyl-2-propenoic acid 2-oxo-2-[2,2,2-trifluoro-1-(trifluoromethyl)ethoxy]ethyl ester
• Molecular Formula: C₉H₈F₆O₄
• Molecular Weight: 294.15
• CAS Registry Number: 1176273-30-5
• SMILES: CC(=C)C(=O)OCC(=O)OC(C(F)(F)F)C(F)(F)F

Properties

• Solubility: Very slightly soluble (0.5 g/L) (25 ºC), Calc.^*
• Density: 1.386±0.06 g/cm³ (20 ºC 760 Torr), Calc.^*
• Boiling point: 200.5±40.0 ºC (760 Torr), Calc.^*
• Flash point: 73.3±22.2 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2017 ACD/Labs)

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P305+P351+P338-P302+P352

Discovory and Applicatios

2-Oxo-2-[2,2,2-trifluoro-1-(trifluoromethyl)ethoxy]ethyl 2-methyl-2-acrylate, also known as 2-Oxo-2-(2,2,2-trifluoro-1-(trifluoromethyl)ethoxy)ethyl methacrylate, is a special monomer known for its unique functional group combination and fluorination characteristics. The development of this compound stems from the exploration of monomers that impart advanced properties to polymers, such as higher chemical stability and resistance to harsh environments. The synthesis usually starts with the synthesis of 2,2,2-trifluoro-1-(trifluoromethyl)ethanol, a fluorinated alcohol known for its high electronegativity and resistance to degradation. This fluorinated alcohol is reacted with 2-Oxo-2-chloroethyl methacrylate, where the chlorine atom is replaced by the fluorinated alcohol to form an ester bond, yielding 2-Oxo-2-[2,2,2-trifluoro-1-(trifluoromethyl)ethoxy]ethyl 2-methyl-2-acrylate.

The 2-methyl-2-acrylic acid (methacrylic acid) moiety in the chemical structure of this compound allows the compound to polymerize and form long chains or networks. The 2-oxo-2-[2,2,2-trifluoro-1-(trifluoromethyl)ethoxy]ethyl group provides the fluorine atom, which enhances chemical resistance, thermal stability, and reduces surface energy. The 2-oxo group provides a site for further chemical modification and reactivity.

This compound is used as a monomer in the synthesis of high-performance polymers. After polymerization, it imparts chemical resistance, thermal stability, and low surface energy to the resulting material. These polymers are used in applications that require durability, longevity, and the ability to withstand extreme conditions, such as in the aerospace, automotive, and electronics industries.

Due to its fluorinated nature, this compound is used in the formulation of optical coatings. The polymers derived from it have a low refractive index and high transparency, making them ideal for anti-reflective coatings and protective layers on optical lenses, displays, and other transparent surfaces.

The low surface energy of the fluorinated component makes polymers derived from this monomer effective as surface modifiers. They can be applied to surfaces to form non-stick, hydrophobic or oleophobic coatings that can be used in applications such as cookware, textiles and packaging materials that require stain or fouling resistance.

In materials engineering, this compound is used to make advanced composites with excellent mechanical properties. Incorporation of fluorinated methacrylate monomers into the composite matrix enhances its resistance to chemical attack, UV degradation and thermal stress. Chemical stability and resistance make this compound suitable for the development of membranes for filtration and separation technologies for processes such as water purification, gas separation and chemical processing. This compound is also used to develop adhesives and sealants that require high bond strength and resistance to solvents and environmental factors.

In chemical synthesis, the methacrylate group in 2-methyl-2-acrylic acid 2-oxo-2-[2,2,2-trifluoro-1-(trifluoromethyl)ethoxy]ethyl ester can act as a cross-linking agent to form a network of polymer chains. This compound can be used as a functional monomer to make specialized polymers with tailored properties such as enhanced hydrophobicity, enhanced thermal resistance or improved optical properties. The reactive groups of this compound allow for further chemical modifications, making it a valuable intermediate for the synthesis of more complex chemical entities.