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Description
TCI D3882 1,3-Dicyclohexylimidazolium Chloride is an imidazolium salt that functions as a precursor to N-heterocyclic carbene ligands, commonly abbreviated as ICy·HCl in the catalysis literature. Its molecular structure consists of an imidazolium ring bearing two cyclohexyl groups on both nitrogen atoms, paired with a chloride counter-anion. In the laboratory, this compound serves as a practical source of carbon-donor ligands: once deprotonated with a strong base, it releases the free carbene, which immediately coordinates to a transition metal centre to form the catalytically active complex.
The principal reason for choosing this material is its ease of handling. Unlike free carbenes, which are highly sensitive to air and moisture, the imidazolium salt is far more stable, so it can be weighed and stored using ordinary laboratory procedures and then activated in situ at the moment the reaction is carried out. The cyclohexyl groups deliver strong donor character combined with steric bulk that remains flexible, because the aliphatic rings can adjust their conformation — in contrast to the more rigid behaviour of aryl-substituted ligands. This steric and electronic profile is frequently advantageous for substrates that require a particular coordination environment.
In Indonesian laboratories, this reagent is typically used in synthetic and catalysis research settings, including university chemistry departments, government research institutes, and industrial R&D laboratories that develop metal-catalysed transformations. It is normally purchased in small research quantities, since the ligand precursor is used in catalytic or stoichiometric-ligand amounts rather than as a bulk raw material. Work is generally performed on a laboratory bench with standard glassware, and the salt is introduced into the reaction system before base-mediated activation.
Laboratory Applications
- N-Heterocyclic carbene ligand preparation — deprotonation with a strong base converts the salt directly into the free ICy carbene, giving researchers a stable, weighable starting point instead of an air-sensitive carbene.
- Transition metal complex synthesis — the liberated carbene coordinates readily to transition metal centres, allowing systematic assembly of defined NHC–metal complexes for structural and reactivity studies.
- Homogeneous catalysis research — the strongly donating cyclohexyl-substituted carbene stabilises the metal centre in solution, making the salt a convenient entry point for developing and screening catalytic systems.
- In situ catalyst generation — because the imidazolium salt is bench-stable, it can be combined with base and metal precursor within the reaction vessel, avoiding isolation of sensitive intermediates.
- Ligand steric and electronic screening — the flexible aliphatic cyclohexyl substituents provide an adjustable steric profile, useful when comparing donor ligands against more rigid aryl-substituted NHC precursors in method development.
Specifications
- Brand: TCI (Tokyo Chemical Industry)
- CAS Number: 181422-72-0
- Catalogue Number: D3882
- Category: Chemistry > Catalysis and Inorganic Chemistry > Carbon-Donor Ligands [Catalysis]
- Pack Sizes: available in research-scale laboratory pack sizes; please confirm the currently offered packaging when ordering
- Storage: keep the container tightly closed and protected from moisture
Handling and Storage
Store the container tightly closed in a cool, dry, well-ventilated area, away from moisture and from incompatible reagents such as strong bases and strong oxidising agents. Imidazolium salts are generally hygroscopic in character, so keep the original supplier container sealed, or transfer material into a tightly capped glass or chemically compatible bottle; a desiccator or sealed secondary container helps limit moisture uptake during storage. Weigh and transfer the solid in a fume hood or well-ventilated workspace, and where the compound will be used for carbene generation, handle it under inert-atmosphere technique. Wear safety glasses, gloves, and a laboratory coat, avoid generating dust, and wash hands thoroughly after handling. Always consult the manufacturer's Safety Data Sheet before use, and follow institutional procedures for chemical waste disposal.
