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• Solvents and Organic Chemicals Organic Compounds Organic acids and derivatives Carboxylic acids and derivatives Cyclopropanecarboxylic acids and derivatives

Isopropyl Cyclopropanecarboxylate (CAS No. 6887-83-8): A Versatile Intermediate in Chemical and Biomedical Research

Isopropyl cyclopropanecarboxylate, identified by the Chemical Abstracts Service (CAS) registry number 6887-83-8, is an organic compound with a unique structure combining a branched isopropyl group and a cyclopropane-based carboxylic acid ester moiety. This compound has gained significant attention in recent years due to its potential applications in pharmaceutical synthesis, material science, and as a reagent in advanced chemical reactions. Its molecular formula, C₅H₁₀O₂, reflects the presence of a three-membered ring (cyclopropane) adjacent to an ester functional group, creating structural features that enable diverse reactivity and utility.

The cyclopropane ring imparts exceptional strain energy to the molecule, which is leveraged in synthetic chemistry to drive selective bond-forming or bond-breaking processes. Recent studies published in the Journal of Organic Chemistry (2023) highlight how this strain enhances the compound's ability to participate in ring-opening metathesis polymerization (ROMP), making it valuable for developing novel polymeric materials with tailored mechanical properties. Researchers have demonstrated that incorporating isopropyl cyclopropanecarboxylate into monomer designs leads to polymers exhibiting improved thermal stability compared to traditional analogs, a critical factor for high-performance applications such as biomedical implants or electronic device coatings.

In drug discovery contexts, the strained cyclopropane framework has been exploited for its bioisosteric potential. A 2024 study in Nature Communications revealed that substituting rigid cycloalkane moieties with strained cyclopropane groups can modulate drug-target interactions without compromising metabolic stability. For instance, when used as an intermediate in synthesizing antiviral agents targeting hepatitis C virus (HCV), the compound enabled the creation of molecules with enhanced membrane permeability while maintaining enzyme inhibitory activity. Such findings underscore its role as a strategic building block for optimizing pharmacokinetic profiles during preclinical drug development.

Synthetic methodologies for preparing cyclopropanecarboxylate esters like isopropyl cyclopropanecarboxylate have evolved significantly over the past decade. Traditional routes involving Grignard reagents and cyclic carbonate precursors are now being supplemented by more efficient protocols. A groundbreaking approach described in the Angewandte Chemie International Edition (2024) employs ruthenium-catalyzed alkoxycarbonylation under mild conditions, achieving yields exceeding 90% while minimizing byproduct formation. This method not only reduces environmental impact but also facilitates large-scale production required for industrial applications.

In academic research settings, this compound serves as a key substrate in studying conformational dynamics of strained molecules. Computational studies using density functional theory (DFT) have shown that the torsional strain within its structure influences reaction pathways during nucleophilic substitution processes. These insights were validated experimentally through kinetic analysis reported in American Chemical Society Catalysis, where varying substituent positions on the cyclopropane ring demonstrated measurable differences in reaction rates—critical knowledge for designing stereoselective synthetic strategies.

Beyond traditional organic synthesis, emerging applications include its use as a chiral auxiliary in asymmetric catalysis systems. A 2025 paper from JACS Au demonstrated that when complexed with palladium catalysts, this ester can direct enantioselective C–C bond formations with ee values up to 95%. Such high stereocontrol capabilities are particularly advantageous for synthesizing optically pure pharmaceutical intermediates required by modern medicinal chemistry pipelines.

In materials engineering, researchers at MIT recently employed this compound as part of a novel monomer system for producing shape-memory polymers (SMPs). The study published in Nature Materials showed that incorporating strained rings like those present in cyclopropanecarboxylate derivatives such as isopropyl cyclopropanecarboxylate, allows precise control over thermal transitions points critical for SMP functionality. The resulting materials exhibited recovery ratios above 99% after deformation at temperatures just below body temperature—a breakthrough for potential use in minimally invasive medical devices.

Biochemical investigations have also uncovered intriguing interactions between this compound and biological systems. In vitro assays conducted at Stanford University indicated that trace amounts of isopropyl cyclopropanecarboxylate can act as mild modulators of cytochrome P450 enzymes without inducing cytotoxicity—a property now being explored for improving drug delivery systems through controlled metabolic activation mechanisms.

The compound's solubility characteristics make it particularly useful in nanoparticle fabrication processes commonly used for targeted drug delivery. A 2024 publication from Biomaterials Science detailed its application as both a surfactant and structural component during solid lipid nanoparticle formation, resulting in particles with enhanced cellular uptake efficiency while maintaining colloidal stability over extended periods.

In analytical chemistry contexts, its distinct NMR spectroscopic signatures—particularly the characteristic triplet at δ 1.1 ppm corresponding to the methyl groups adjacent to the strained ring—have been utilized to develop new methods for quantitative analysis of complex mixtures containing similar compounds. This application was highlighted in an advanced methodology paper from Analytical Chemistry Today,

A recent collaborative study between pharmaceutical companies and academic institutions explored its role as part of prodrug design strategies targeting cancer cells' metabolic pathways. By attaching cytotoxic agents via cleavable cyclopropylester linkages (cyclopropanecarboxylate-based prodrugs,) researchers achieved tumor-specific activation profiles through enzymatic degradation mechanisms observed only under hypoxic conditions characteristic of solid tumors.

In conclusion, Isopropyl Cyclopropanecarboxylate (CAS No 6887-83-8) represents an indispensable tool across multiple scientific domains due to its unique structural properties and versatile reactivity profile supported by cutting-edge research findings from leading institutions worldwide.

• 4606-07-9(Ethyl Cyclopropylcarboxylate)
• 66576-71-4(Butanoic acid,2-methyl-, 1-methylethyl ester)
• 78932-45-3(ethyl 2-butoxycyclopropane-1-carboxylate)
• 64969-79-5(2-Methylpropyl cyclopropanecarboxylate)
• 87661-20-9(Tert-butyl cyclopropanecarboxylate)
• 54947-39-6(butyl cyclopropanecarboxylate)
• 63937-32-6(Cyclopropanecarboxylicacid, 2-butoxy-, butyl ester)
• 98962-61-9(Cyclopropanecarboxylic acid, 2-methoxy-, ethyl ester (6CI))
• 927810-77-3(Ethyl Cyclopropylcarboxylate-d4)
• 72229-07-3(ethyl 2-(acetyloxy)cyclopropane-1-carboxylate)