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Description
TCI D3870 1,3-Dimesitylimidazol-2-ylidene, widely known by the abbreviation IMes, is an isolated free N-heterocyclic carbene supplied ready to use as a carbon-donor ligand. Unlike imidazolium salts, which still require a deprotonation step before they can be used, this compound is already in its active carbene form and can therefore be coordinated directly to a transition metal centre. Its role in the laboratory is to provide a strongly donating ligand for the preparation of catalytic complexes based on palladium, nickel, copper, ruthenium, gold, and other metals employed in modern organic synthesis.
The characteristics that make IMes so highly valued are its sigma-donor strength, which far exceeds that of conventional phosphines, combined with the steric bulk of the two mesityl groups flanking the carbene centre. This combination produces a strong, thermally robust metal–ligand bond, accelerates the oxidative addition step, and promotes reductive elimination, so that many coupling reactions can proceed at low catalyst loadings. NHC-ligated complexes also tend to be more resistant to decomposition than their phosphine analogues, which translates into longer-lived catalytic systems and more reproducible results across repeated runs.
In Indonesian laboratories, this reagent is typically used in university and institutional research groups as well as in industrial R&D units working on catalyst development and methodology studies in organic synthesis. It is normally handled on a small scale under inert conditions, using a glovebox or Schlenk line, for the in-house preparation of metal–NHC complexes that are then applied in cross-coupling and related transformations. Because the free carbene is highly sensitive as a direct consequence of its reactivity, it is generally reserved for work where dry, air-free technique is already routine.
Laboratory Applications
- Preparation of palladium–NHC catalysts: the isolated free carbene coordinates directly to palladium precursors without a separate deprotonation step, giving well-defined complexes for cross-coupling chemistry.
- Nickel and copper complex synthesis: the strong sigma-donation of IMes stabilises these first-row metal centres, supporting catalyst systems intended to replace more costly precious-metal alternatives.
- Ruthenium catalyst development: the thermally robust metal–ligand bond formed by this carbene suits ruthenium complexes used in demanding transformations that require prolonged heating.
- Gold complex preparation: the bulky mesityl substituents provide the steric protection around the metal centre that gold–NHC species require for defined coordination and handling.
- Low-loading coupling reaction studies: because IMes accelerates oxidative addition and promotes reductive elimination, it enables catalytic screening work at reduced catalyst loadings.
Specifications
- Brand: TCI
- Product code: D3870
- CAS number: 141556-42-5
- Chemical name: 1,3-Dimesitylimidazol-2-ylidene (IMes)
- Category: Chemistry > Catalysis and Inorganic Chemistry > Carbon-Donor Ligands [Catalysis]
- Storage note: air- and moisture-sensitive free carbene; store under inert gas — please refer to the TCI catalogue and product label for available pack sizes and the manufacturer's stated storage temperature
Handling and Storage
As a free N-heterocyclic carbene, this material is highly sensitive to air and moisture and must be stored under an inert atmosphere such as dry nitrogen or argon. Keep the container tightly closed in its original packaging, or transfer the contents to a Schlenk flask or a sealed vial held inside a glovebox. Weighing and transfer operations should be carried out under inert conditions using dry solvents and oven-dried or flame-dried glassware. Work in a well-ventilated fume hood, wear gloves, safety glasses, and a laboratory coat, and avoid contact with water or ambient air. Always consult the manufacturer's safety data sheet before use, and follow your institution's procedures for the disposal of reactive organometallic waste.
