2-Methyl-2-propenoic acid 1-(1,1-dimethylethyl)cyclopentyl ester
[CAS# 1179475-19-4]

Identification

• Name: 2-Methyl-2-propenoic acid 1-(1,1-dimethylethyl)cyclopentyl ester
• Molecular Formula: C₁₃H₂₂O₂
• Molecular Weight: 210.31
• CAS Registry Number: 1179475-19-4
• SMILES: CC(=C)C(=O)OC1(CCCC1)C(C)(C)C

Properties

• Solubility: Very slightly soluble (0.16 g/L) (25 ºC), Calc.^*
• Density: 0.93±0.1 g/cm³ (20 ºC 760 Torr), Calc.^*
• Boiling point: 252.9±9.0 ºC (760 Torr), Calc.^*
• Flash point: 98.9±16.1 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2018 ACD/Labs)

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H227
• Precautionary Statements: P210-P264-P270-P280-P301+P312-P330-P370+P378-P403+P235-P501

Discovory and Applicatios

2-Methyl-2-propenoic acid 1-(1,1-dimethylethyl)cyclopentyl ester, commonly known as tert-butylcyclopentyl methacrylate, is a special monomer in the field of polymer chemistry. The discovery of tert-butylcyclopentyl methacrylate can be traced back to research efforts in the mid-20th century aimed at developing monomers that would improve polymer properties. Researchers sought to combine the well-known polymerizability of methacrylates with the steric effects introduced by the large tert-butyl group attached to the cyclopentane ring to create materials with better resistance to thermal degradation and mechanical stress.

The synthesis of tert-butylcyclopentyl methacrylate generally involves the following steps: tert-butylcyclopentanol is synthesized by alkylating cyclopentanol with tert-butyl bromide in the presence of a base. tert-butylcyclopentanol is then esterified with methacryloyl chloride or methacrylic acid in the presence of a suitable catalyst. The reaction forms an ester bond to give 2-methyl-2-propenoic acid 1-(1,1-dimethylethyl)cyclopentyl ester. The 2-methyl-2-propenoic acid (methacrylic acid) component of the compound facilitates polymerization. Tert-butylcyclopentyl is a bulky, sterically hindered group that imparts rigidity to the polymer backbone and enhances thermal stability. The cyclopentyl group provides additional steric hindrance and affects the overall polymer structure by influencing chain packing and flexibility.

Incorporating tert-butylcyclopentyl methacrylate into polymers improves the thermal stability and resistance to degradation of the material. These properties are critical for applications where the material is exposed to high temperatures or harsh environments, such as automotive parts, aerospace components, and electronics. Polymers derived from this monomer exhibit improved mechanical strength and stiffness. The bulky tert-butylcyclopentyl group restricts chain mobility, allowing the polymer to withstand mechanical stress and maintain its structural integrity under load. Tert-butylcyclopentyl methacrylate can be copolymerized with other monomers to tune the properties of the resulting polymer. Copolymers can be designed to balance rigidity and flexibility, optimize thermal properties, or enhance chemical resistance, making them suitable for a variety of industrial applications.

The compound is used to develop advanced coatings with high durability and resistance to environmental factors. These coatings are used in industrial and consumer products to provide a protective layer against wear, corrosion, and chemical attack. Tert-Butylcyclopentyl methacrylate is used to formulate adhesives and sealants that require high bond strength and stability. The enhanced mechanical properties of the resulting polymers ensure reliable performance in demanding applications such as the construction, automotive, and aerospace industries. The unique properties of this monomer are valuable in producing specialty polymers with specific functionalities. These polymers can be designed for use in high-performance composites, flexible electronics, and other cutting-edge applications where traditional materials may not be sufficient.

As a functional monomer, tert-Butylcyclopentyl methacrylate is incorporated into polymers to introduce steric bulk and rigidity. The methacrylate group allows the compound to act as a crosslinker in the synthesis of crosslinked polymers and gels. These materials exhibit improved mechanical properties and stability. The reactive methacrylate group can also serve as a starting point for further chemical modifications, allowing the synthesis of complex molecules and polymers with tailored properties.