3-Cyclohexenyl 3-cyclohexene 1-carboxylate
[CAS# 2611-00-9]

Identification

• Classification: Chemical reagent >> Organic reagent >> Ester
• Name: 3-Cyclohexenyl 3-cyclohexene 1-carboxylate
• Synonyms: 3-Cyclohexene-1-carboxylic acid 3-cyclohexen-1-ylmethyl ester
• Molecular Formula: C₁₄H₂₀O₂
• Molecular Weight: 220.31
• CAS Registry Number: 2611-00-9
• EC Number: 220-031-5
• SMILES: C1CC(CC=C1)COC(=O)C2CCC=CC2

Properties

• Solubility: 1.94 mg/L (25 ºC water)
• Density: 1.0±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.508, Calc.^*
• Melting point: 46.89 ºC
• Boiling Point: 303.8±21.0 ºC (760 mmHg), Calc.^*, 298.76 ºC
• Flash Point: 130.2±9.6 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H413
• Precautionary Statements: P264-P270-P273-P301+P317-P330-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413

Discovory and Applicatios

3-Cyclohexenyl 3-cyclohexene 1-carboxylate is an organic compound that belongs to the family of cyclic esters, characterized by the presence of two cyclohexene rings and a carboxylate ester linkage. This compound is of interest in the fields of organic synthesis and materials science due to its structural characteristics, which impart useful chemical and physical properties. The discovery of cyclic esters like 3-cyclohexenyl 3-cyclohexene 1-carboxylate stems from the early 20th century when chemists explored the chemistry of cyclic hydrocarbons and esters to develop novel compounds for industrial and scientific use.

The molecular structure of 3-cyclohexenyl 3-cyclohexene 1-carboxylate consists of a cyclohexene ring attached to another cyclohexene ring through a carboxylate group (-COO). This unique configuration allows the compound to possess properties typical of esters, such as moderate reactivity and the ability to participate in a variety of chemical reactions, while the presence of the cyclohexene rings adds rigidity and stability to the molecule.

One of the key applications of 3-cyclohexenyl 3-cyclohexene 1-carboxylate is in the field of polymer chemistry. Due to its cyclic structure, this compound is used as a monomer or a building block in the synthesis of advanced polymers. The presence of the carboxylate group allows it to easily undergo polymerization reactions, particularly in combination with other monomers that have complementary functional groups. Polymers formed from such cyclic esters are known for their mechanical strength, chemical resistance, and thermal stability, which makes them suitable for use in high-performance materials.

In materials science, polymers derived from 3-cyclohexenyl 3-cyclohexene 1-carboxylate are explored for their potential in creating durable and lightweight plastics. These plastics can be used in automotive parts, construction materials, and even consumer goods where a combination of strength and flexibility is required. The rigidity of the cyclohexene rings contributes to the strength of the final polymer, while the ester linkage provides flexibility, making these materials both durable and adaptable to a variety of applications.

The pharmaceutical industry has also shown interest in the use of cyclic esters like 3-cyclohexenyl 3-cyclohexene 1-carboxylate. The ester functionality allows the compound to act as an intermediate in the synthesis of more complex molecules, particularly those with biological activity. In medicinal chemistry, esters are often used as prodrugs, where the ester bond is cleaved in the body to release the active drug. While 3-cyclohexenyl 3-cyclohexene 1-carboxylate itself may not be directly used as a drug, its structural elements can serve as scaffolds in the design of biologically active compounds.

Additionally, this compound has potential applications in coatings and adhesives. The reactivity of the carboxylate group allows 3-cyclohexenyl 3-cyclohexene 1-carboxylate to be incorporated into resins that can be cured to form strong, protective films. These coatings are used in industries such as aerospace and marine engineering, where materials must withstand harsh environmental conditions. The cyclohexene structure also provides the resulting polymers with resistance to degradation, further enhancing the durability of the coatings.

The discovery and development of cyclic esters like 3-cyclohexenyl 3-cyclohexene 1-carboxylate have contributed significantly to advancements in polymer science, materials engineering, and organic synthesis. The compound’s unique structure makes it a versatile component in the creation of advanced materials and specialty chemicals. Ongoing research continues to explore its potential in new applications, particularly as industries seek materials with enhanced performance characteristics for use in challenging environments.

References

(1) U.S. Department of Health and Human Services, Public Health Service, Center for Disease Control, National Institute for Occupational Safety Health. Registry of Toxic Effects of Chemical Substances (RTECS). National Library of Medicine's current MEDLARS file., p. 83/7908.

(2) Hawley, G.G. The Condensed Chemical Dictionary. 9th ed. New York: Van Nostrand Reinhold Co., 1977., p. 285.