1,3-Dimesitylimidazolium-2-carboxylate TCI D5401

Chemical Identity

Other names: IMes·CO2 · 1,3-Bis(2,4,6-trimethylphenyl)imidazolium-2-carboxylate · IMes.CO2
CAS No.: 675877-56-2
PubChem: CID 15605852·SID 354335707
Formula: C22H24N2O2
Molecular weight: 348.45 g/mol
Purity: >95.0%(HPLC)(T)

Full identifiers (IUPAC, SMILES, InChIKey)

IUPAC: 1,3-bis(2,4,6-trimethylphenyl)imidazol-1-ium-2-carboxylate
SMILES: CC1=CC(=C(C(=C1)C)N2C=C[N+](=C2C(=O)[O-])C3=C(C=C(C=C3C)C)C)C
InChIKey: NEHHJWFJQYAIPS-UHFFFAOYSA-N

Rp 2.544.150,00

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1,3-Dimesitylimidazolium-2-carboxylate is a chemical compound widely used in catalytic reactions and organic synthesis. It plays a crucial role in laboratory settings where efficient and selective catalysts are required. This compound is particularly valuable in heterogeneous catalysis and metal activation processes due to its ability to interact strongly with transition metals. Its unique molecular structure enables it to act as a versatile ligand, making it an essential component in various chemical research applications.

The compound is known for its chemical stability under controlled conditions, which makes it reliable for use in laboratory experiments. However, it is highly sensitive to moisture and air exposure, necessitating careful handling and storage. These properties make it a preferred choice for researchers seeking a stable yet reactive material. Its ability to form complexes with metals further enhances its utility in coordination chemistry and catalytic systems.

In Indonesian laboratories, 1,3-Dimesitylimidazolium-2-carboxylate is commonly used in both fundamental and applied chemical research. It is a favored material for experiments requiring efficient and specific catalysts. Its availability in the local market supports ongoing research efforts, enabling scientists to conduct experiments with reliable and high-quality reagents. This compound is integral to advancing chemical processes in academic and industrial research environments.

Advantages (TCI brochure)

NHC ligands and catalysts are preparable by heating.
No salt generated during preparation.
Applicable under neutral conditions.
NHC-CO2 adducts release CO2.

TCI brochures (PDF)

Easily-preparable N-Heterocyclic Carbene (NHC) Precursors 2021-09-14 · p. 1
N-Heterocyclic Carbene (NHC) Ligands and Metal Complexes 2026-02-10 · p. 1
Ligands 2025-12-01 · p. 8
Suzuki-Miyaura Cross Coupling Reaction 2025-12-01 · p. 26

Related TCI products

Organic synthesis reactions benefit from this compound due to its ability to activate transition metals and enhance reaction efficiency.
Heterogeneous catalysis applications rely on its strong interaction with metal surfaces, improving reaction rates and selectivity.
Coordination chemistry studies use it as a ligand to form stable metal complexes, aiding in the investigation of bonding and reactivity.
Metal activation processes utilize its structural properties to facilitate electron transfer and catalytic activity.
Research in green chemistry leverages its efficiency in reducing energy consumption and waste production during chemical transformations.

From the TCI brochure

Transition metal/NHC complex catalyst preparation
NHC-catalyzed conjugate cyanations

Brand	TCI
CAS number	675877-56-2
Molecular formula	—
Purity	—
Category	Chemistry > Catalysis and Inorganic Chemistry > Carbon-Donor Ligands [Catalysis]
Pack sizes	—
Physical form	—
Storage	Keep in a dry, cool place away from moisture and air exposure.

Data from the TCI brochure

Yield conjugate cyanation	>78% (10 mol % D5401, Me3Si-CN, 1,4-dioxane, rt, 25 examples)

Source: TCI brochure RR119 (2021-09-14)

This compound should be stored in a dry, cool environment to prevent moisture and air exposure, which can degrade its properties. It is recommended to use airtight containers made of inert materials such as glass or polyethylene to maintain its stability. Due to its sensitivity, it should be handled in a controlled laboratory setting with appropriate ventilation. Researchers should avoid prolonged exposure to air and moisture during storage and use. Proper labeling and storage conditions are essential to ensure the compound remains effective for its intended applications. Always follow standard laboratory safety protocols when working with this material.

References cited in the TCI brochure

Adelina M. Voutchkova. Disubstituted Imidazolium-2-Carboxylates as Efficient Precursors to N-Heterocyclic Carbene Complexes of Rh, Ru, Ir, and Pd Journal of the American Chemical Society, 2005. doi:10.1021/ja056625k
Prithwish Goswami. N-Heterocyclic Carbene Catalyzed 1,6-Conjugate Addition of Me3Si-CN to para-Quinone Methides and Fuchsones: Access to α-Arylated Nitriles Organic Letters, 2017. doi:10.1021/acs.orglett.7b00508