ChemicalBook Product Catalog Chemical Reagents Organic reagents Polycyclic compound 1,3-BIS(2,4,6-TRIMETHYLPHENYL)IMIDAZOL-2-YLIDENE

1,3-BIS(2,4,6-TRIMETHYLPHENYL)IMIDAZOL-2-YLIDENE

1,3-BIS(2,4,6-TRIMETHYLPHENYL)IMIDAZOL-2-YLIDENE Basic information
Reaction
Product Name:1,3-BIS(2,4,6-TRIMETHYLPHENYL)IMIDAZOL-2-YLIDENE
Synonyms:1,3-BIS(2,4,6-TRIMETHYLPHENYL)IMIDAZOL-2-YLIDENE;1,3-Bis(2,4,6-trimethylphenyl)imidazol-2-ylidene,min.98%;1,3-BIS(2,4,6-TRIMETHYLPHENYL)IMIDAZOL-2-YLIDENE, MIN. 98%;1,3-Bis(2,4,6-trimethylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene;1,3-Dimesitylimidazol-2-ylidene;IMes;1,3-Bis(2,4,6-triMethylphenyl)-1,3-dihydro-2H-iMidazol-2-yli;2H-IMidazol-2-ylidene, 1,3-dihydro-1,3-bis(2,4,6-triMethylphenyl)-
CAS:141556-42-5
MF:C21H24N2**
MW:304.42866
EINECS:
Product Categories:N-heterocyclic carbene
Mol File:141556-42-5.mol
1,3-BIS(2,4,6-TRIMETHYLPHENYL)IMIDAZOL-2-YLIDENE Structure
1,3-BIS(2,4,6-TRIMETHYLPHENYL)IMIDAZOL-2-YLIDENE Chemical Properties
Melting point 140 °C
storage temp. -20°C
form Powder
color white to off-white
Sensitive air sensitive, moisture sensitive
Safety Information
Hazard Codes Xi
Risk Statements 10-36/37/38
Safety Statements 26
RIDADR UN 1325 4.1/PG 3
WGK Germany 3
HS Code 2933.29.9000
MSDS Information
1,3-BIS(2,4,6-TRIMETHYLPHENYL)IMIDAZOL-2-YLIDENE Usage And Synthesis
ReactionNucleophilic carbene that serves as a bulky, electron-rich "phosphine mimic" for metal-catalyzed reactions.
(a) Palladium-catalyzed Suzuki cross-coupling of aryl chlorides.
(b) Ruthenium-carbene complexes serve as more reactive catalyst for ring-closing metathesis. Reactions of 141556-42-5

Uses1,3-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.
1,3-BIS(2,4,6-TRIMETHYLPHENYL)IMIDAZOL-2-YLIDENE Preparation Products And Raw materials
Raw materials1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride
Diethyl 1,3-acetonedicarboxylate 1,3-Bis(2,6-di-isopropylphenyl)imidazol-2-ylidenegold(I)chloride,95% 1,3-Bis[2,6-bis(1-methylethyl)phenyl]-2-(trichloromethyl)-imidazolidine 1,3-BIS(2,6-DIISOPROPYLPHENYL)-IMIDAZOLIDINIUM-CHLORIDE 1,3-Diphenylacetone 1,3-Propane sultone 1,3-BIS(2,6-DI-I-PROPYLPHENYL)IMIDAZOL-2-YLIDENE 1,3-Bis(2,6-di-i-propylphenyl)-4,5-dihydroimidazol-2-ylidine,min.98% 1,3-Diiodopropane N,N'-Diethylthiourea 1,3-Dichloropropane 1,3-Butadiene 1,3-Indanedione 1,3-Dichloro-5,5-dimethylhydantoin 1,3-Benzenedimethanol 1,3-Bis (2,6-diisopropylphenyl) imidazolium chloride 4-Amino-TEMPO, free radical 1,3-BIS(2,4,6-TRIMETHYLPHENYL)IMIDAZOL-2-YLIDENE
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