1,3-Dimesityl-1H-imidazol-3-ium-2-ide

Base Information

• Chemical Name: 1,3-Dimesityl-1H-imidazol-3-ium-2-ide
• CAS No.: 141556-42-5
• Molecular Formula: C21H24 N2
• Molecular Weight: 304.435
• Hs Code.: 2933290090
• European Community (EC) Number: 625-734-4
• DSSTox Substance ID: DTXSID70456010
• Wikipedia: IMes
• Wikidata: Q17125083
• Mol file: 141556-42-5.mol

Synonyms:141556-42-5;1,3-Dimesityl-1H-imidazol-3-ium-2-ide;1,3-Dimesitylimidazol-2-ylidene;1,3-BIS(2,4,6-TRIMETHYLPHENYL)IMIDAZOL-2-YLIDENE;IMes;1,3-Bis(2,4,6-trimethylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene;1,3-bis(2,4,6-trimethylphenyl)-2H-imidazol-1-ium-2-ide;1,3-Bis(2,4,6-trimethylphenyl)imidazol-2-ylidene, min. 98%;YSWG291;DTXSID70456010;MFCD09265338;AKOS016000596;AB89797;SC11699;BS-44007;CS-0095580;D3870;1,3-bis(2,4,6-trimethylphenyl)-imidazolium;Q17125083;1,3-Bis(2,4,6-trimethylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene, 97%;1,3-BIS(2,4,6-TRIMETHYLPHENYL)-1,3-DIHYDRO-2H-IMIDAZOL-2-YLIDENE;1,3-DIMESITYLIMIDAZOL-2-YLIDENE;IMES

Chemical Property of 1,3-Dimesityl-1H-imidazol-3-ium-2-ide

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 140 °C
• Boiling Point: 442.706°C at 760 mmHg
• Flash Point: 199.09°C
• PSA: 6.48000
• LogP: 5.17470
• Storage Temp.: ?20°C
• Sensitive.: air sensitive, moisture sensitiv
• XLogP3: 5.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 304.193948774
• Heavy Atom Count: 23
• Complexity: 414

Purity/Quality:

97% ^*data from raw suppliers

1,3-Bis(2,4,6-trimethylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=C(C(=C1)C)N2C=C[N+](=[C-]2)C3=C(C=C(C=C3C)C)C)C
• Uses: 1,3-Bis(2,4,6-trimethylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene (IMes) is a nucleophilic N-heterocyclic carbene (NHC) ligand.It can be used to synthesize: IMes ligated-rhodium complex as a catalyst for the selective hydrogenation of substituted aryl and heteroaryl boronate esters to cis-substituted borylated cycloalkanes.IMes/ruthenium complex (Cp*Ru(IMes)Cl)(Cp* =η5-C5Me3) as a catalyst for olefin ring closing metathesis reaction. IMes is also used as an ancillary ligand in Pd-catalyzed Suzuki-Miyaura cross-coupling reaction between aryl chlorides or aryl triflates and arylboronic acids.

Technology Process of 1,3-Dimesityl-1H-imidazol-3-ium-2-ide

There total 7 articles about 1,3-Dimesityl-1H-imidazol-3-ium-2-ide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 84.0%

1,3-bis(mesityl)imidazolium chloride (141556-45-8) → [1,3-bis(2,4,6-trimethylphenyl)imidazol]-2-ylidene (141556-42-5)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; for 0.333333h; Ambient temperature;

DOI:10.1021/ja00040a007

Reference yield: 84.0%

1,3-dimesitylimidazolium tetrafluoroborate → [1,3-bis(2,4,6-trimethylphenyl)imidazol]-2-ylidene (141556-42-5)

Guidance literature:

With potassium tert-butylate; sodium hydride; In tetrahydrofuran; for 12h; Schlenk technique; Inert atmosphere;

DOI:10.1021/acs.organomet.7b00838

Reference yield: 0.5%

pentakis(dimethylamido)tantalum (19824-59-0) + 1,3-bis(mesityl)imidazolium chloride (141556-45-8) → (alphaIMes)TaCl2(NMe2)3 + [(IMesH)(IMes)][fac-TaCl3(NMe2)3] + [1,3-bis(2,4,6-trimethylphenyl)imidazol]-2-ylidene (141556-42-5)

Guidance literature:

In tetrahydrofuran; at 60 ℃; for 18h; Schlenk technique; Glovebox;

DOI:10.1039/c7dt00748e

upstream raw materials:

1,3-bis(mesityl)imidazolium chloride

carbon monoxide

1,3-bis(2,4,6-trimethylphenyl)imidazole hydrochloride

pentakis(dimethylamido)tantalum

Downstream raw materials:

1,3-bis(2,4,6-trimethyl-phenyl)-1,3-dihydroimidazole-2-thione

bis(1,3-dimesityl-1H-imidazol-2(3H)-ylidene)nickel(0)

InH₃(C₃H₂N₂(C₉H₁₁)2)

Refernces

Investigation of the Catalytic Activity of a 2-Phenylidenepyridine Palladium(II) Complex Bearing 4,5-Dicyano-1,3-bis(mesityl)imidazol-2-ylidene in the Mizoroki-Heck Reaction

10.1002/zaac.201500625

The study investigates the catalytic activity of two palladium(II) complexes, [PdCl(ppy)(IMes)] (4) and [PdCl(ppy){(CN)2IMes}] (6), in the Mizoroki-Heck reaction, a crucial cross-coupling reaction in the synthesis of pharmaceuticals and natural products. These complexes feature different N-heterocyclic carbene (NHC) ligands, IMes and (CN)2IMes, with the latter having a higher π-acceptor strength. The purpose of the study is to evaluate how the π-acceptor strength of the NHC ligands affects the catalytic performance of the complexes. The chemicals used include palladium(II) chloride, 2-phenylpyridine, 1,3-bis(mesityl)imidazol-2-ylidene (IMes), 4,5-dicyano-1,3-bis(mesityl)imidazol-2-ylidene ((CN)2IMes), and aryl halides, which serve as substrates in the Mizoroki-Heck reaction. The study aims to develop more effective precatalysts for this reaction by understanding the influence of the NHC ligands' electronic properties on the reaction's efficiency.