Ethyl adamantane-1-carboxylate
[CAS# 2094-73-7]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: Ethyl adamantane-1-carboxylate
• Synonyms: Ethyl tricyclo[3.3.1.1(3,7)]decane-1-carboxylate
• Molecular Formula: C₁₃H₂₀O₂
• Molecular Weight: 208.30
• CAS Registry Number: 2094-73-7
• EC Number: 218-253-2
• SMILES: CCOC(=O)C12CC3CC(C1)CC(C3)C2

Properties

• Density: 1.1±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.525, Calc.^*, 1.489 (Expl.)
• Boiling Point: 261.8±8.0 ºC (760 mmHg), Calc.^*, 90-91 ºC (expl.)
• Flash Point: 109.9±6.0 ºC, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H317-H319
• Precautionary Statements: P280-P305+P351+P338

Discovory and Applicatios

Ethyl adamantane-1-carboxylate is an organic compound that belongs to the family of adamantane derivatives. Adamantane itself is a hydrocarbon with a unique cage-like structure, which has garnered interest for its applications in a variety of chemical and pharmaceutical contexts. The introduction of an ester group at the 1-position of the adamantane ring system, as in ethyl adamantane-1-carboxylate, opens up additional avenues for its reactivity and potential use in different fields.

The discovery of ethyl adamantane-1-carboxylate is part of ongoing research into the functionalization of adamantane and its derivatives. Adamantane itself has been known since the early 20th century, with its rigid structure and high stability making it an interesting candidate for various applications. The functionalization of adamantane, especially through esterification, allows for the modulation of its properties, including solubility, reactivity, and compatibility with different chemical environments.

Ethyl adamantane-1-carboxylate is synthesized through the esterification of adamantane-1-carboxylic acid with ethanol, a simple reaction that results in the formation of the ester functional group. This compound is typically characterized by standard analytical methods such as nuclear magnetic resonance (NMR) spectroscopy and mass spectrometry (MS), which confirm the structure of the adamantane ring system and the ester functionality.

One of the key applications of ethyl adamantane-1-carboxylate is in the field of medicinal chemistry. Adamantane derivatives, including ethyl adamantane-1-carboxylate, have been explored for their potential pharmacological properties, such as antiviral, anti-inflammatory, and neuroprotective activities. The rigid structure of the adamantane core provides a stable scaffold for the development of drugs that can interact with biological targets, including enzymes and receptors, in a selective and potent manner. Ethyl adamantane-1-carboxylate, with its ester group, may serve as a prodrug or an intermediate in the synthesis of more complex molecules with therapeutic potential.

In addition to its medicinal uses, ethyl adamantane-1-carboxylate also has applications in materials science. The unique structure of adamantane derivatives imparts distinct physical and chemical properties, including rigidity, symmetry, and the ability to form crystalline solids with high melting points. These characteristics make ethyl adamantane-1-carboxylate a potential candidate for use in the development of advanced materials such as molecular sensors, polymers, and nanomaterials. The ester group may also allow for further modification of the compound to tailor its properties for specific applications in organic electronics or catalysis.

Furthermore, ethyl adamantane-1-carboxylate can serve as a versatile building block in organic synthesis. Its reactivity allows it to participate in a variety of chemical reactions, including substitution, reduction, and hydrolysis, making it a valuable intermediate for the synthesis of more complex molecules. Researchers have explored the use of adamantane-based compounds in the development of specialty chemicals, including surfactants, lubricants, and coatings, where the stability and unique structure of adamantane can confer desirable properties.

In conclusion, ethyl adamantane-1-carboxylate is a versatile compound with a range of potential applications in medicinal chemistry, materials science, and organic synthesis. Its unique structure, combined with the ester group, makes it a valuable building block for further chemical development. As research progresses, ethyl adamantane-1-carboxylate may find broader applications in drug design, material innovation, and industrial processes.