Overview
trans-Cyclooctene is an eight-membered cyclic hydrocarbon with a strained trans-configuration double bond, making it a valuable intermediate in synthetic chemistry. Unlike its cis counterpart, the trans isomer is thermodynamically unstable due to ring strain, yet this very property drives its utility in rapid conjugation reactions. First synthesized in the 1960s, it gained prominence in bioorthogonal chemistry for its fast reactivity with tetrazines, enabling applications in live-cell labeling and drug delivery. Its industrial relevance spans specialty polymers and advanced material design.
Physical and Chemical Properties
As a liquid at room temperature, trans-cyclooctene exhibits low density and volatility, typical of medium-sized alkenes. The trans double bond introduces significant angle strain (∼40 kcal/mol), which lowers its activation energy for cycloadditions. Its NMR spectrum shows characteristic olefinic proton shifts at 5.4–5.6 ppm. The compound is stable under inert atmospheres but polymerizes upon prolonged exposure to light or oxygen. Solubility is limited to nonpolar solvents, restricting aqueous-phase applications without derivatization.
Main Applications
In click chemistry, trans-cyclooctene’s rapid reaction with tetrazines (k ∼104 M−1s−1) enables real-time biomolecule tracking, such as in fluorescence microscopy of cellular processes. It also serves as a crosslinker in elastomers, enhancing polymer toughness. Pharmaceutical researchers exploit its bioorthogonality for targeted drug conjugation, while material scientists incorporate it into self-healing coatings. Emerging uses include PET tracer synthesis and DNA nanostructure assembly.
Safety and Storage
Due to flammability (flash point ∼25°C), store trans-cyclooctene in flame-proof refrigerators with nitrogen blanketing. Decomposition can release hazardous fumes, necessitating vented storage containers. Handling requires nitrile gloves and goggles, as skin contact may cause irritation. Spills should be absorbed with inert material (e.g., vermiculite) and disposed as hazardous waste. Always refer to the supplier’s SDS for specific protocols.
B2B Procurement Guide
Bulk buyers should prioritize suppliers offering batch-specific Certificates of Analysis (CoA) confirming purity (≥95%) and residual solvent levels. Custom synthesis options are available for derivatives like TCO-PEG or fluorinated variants. Pricing tiers vary by scale: lab quantities (1–10g) cost $50–200/g, while kilogram orders may drop to $20–50/g. Consider logistical factors—cold chain shipping is often required to prevent degradation during transit.
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