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Description
TCI D3711 1,3-Di-tert-butylimidazolium Tetrafluoroborate is an imidazolium salt bearing two tert-butyl groups on both nitrogen atoms, with a tetrafluoroborate ion serving as the counterbalancing anion. In the laboratory, this compound functions as a precursor to N-heterocyclic carbene ligands, also known as carbon-donor ligands. When treated with a sufficiently strong base, the proton at the C2 position of the imidazolium ring is removed and a free carbene is generated, ready to bind to a transition metal centre. In this way, a stable and easily weighed salt can be converted inside the reaction vessel into an active ligand, so researchers do not need to store the highly sensitive free carbene.
The characteristics that make this material a preferred choice are its binding strength as a ligand and the steric hindrance provided by the tert-butyl groups. N-heterocyclic carbenes are exceptionally strong sigma donors, so the metal complexes they form are generally more stable toward heat and air than phosphine-based complexes. The two tert-butyl groups create a large steric environment around the metal centre, which helps prevent the catalyst from aggregating into inactive particles and encourages the reductive elimination step to proceed more rapidly. These combined electronic and steric features give the ligand precursor its practical value in catalyst preparation.
In Indonesian laboratories, this reagent is typically used in synthetic and catalysis research groups at universities, government research institutes, and industrial R&D units that prepare their own transition metal catalysts rather than purchasing pre-formed complexes. Because the salt is handled as a weighable solid and deprotonated only when needed, it fits well into laboratories where glovebox capacity is limited and where reagents must remain reliable through ambient storage conditions and routine bench handling.
Laboratory Applications
- In situ generation of N-heterocyclic carbene ligands: the C2 proton is removed with a strong base directly in the reaction vessel, producing the active carbene without the need to isolate or store the sensitive free species.
- Preparation of transition metal complexes: the liberated carbene binds readily to transition metal centres, allowing research groups to assemble their own well-defined catalyst complexes from a stable, easily weighed starting salt.
- Cross-coupling catalyst development: the bulky tert-butyl substituents create a crowded metal environment that promotes faster reductive elimination, a property frequently exploited when designing coupling catalysts in the laboratory.
- Studies requiring thermally and air-tolerant catalysts: because N-heterocyclic carbene complexes are generally more robust toward heat and air than phosphine analogues, this precursor suits work where phosphine ligands degrade too readily.
- Investigations of catalyst stability and deactivation: the large steric shielding around the metal centre helps prevent aggregation into inactive particles, making this ligand precursor useful for probing catalyst lifetime and decomposition pathways.
Specifications
- Brand: TCI (Tokyo Chemical Industry)
- CAS number: 263163-17-3
- Category: Chemistry > Catalysis and Inorganic Chemistry > Carbon-Donor Ligands [Catalysis]
- Chemical class: imidazolium salt with tetrafluoroborate counter-anion; N-heterocyclic carbene (carbon-donor) ligand precursor
- Pack sizes: available in the manufacturer's standard catalogue pack sizes; please confirm the current option when ordering
- Storage: keep in the tightly closed original container, protected from moisture; refer to the manufacturer's label and safety data sheet for the specified storage conditions
Handling and Storage
Store the container tightly closed in a cool, dry, well-ventilated area, away from moisture and from incompatible materials such as strong bases, since the reagent is intended to be deprotonated only at the point of use. The original manufacturer's container is the most suitable primary packaging; if transferring, use clean, dry, chemically compatible glass or plastic vessels that seal well, and label them clearly. Weigh and handle the solid in a fume hood or, where the downstream chemistry requires it, under an inert atmosphere, using gloves, safety glasses, and a laboratory coat. Avoid raising dust, keep hygroscopic exposure to a minimum by closing the container promptly, and always consult the manufacturer's safety data sheet before use and for waste disposal guidance.
