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

InChI

InChI=1S/C21H24N2/c1-14-9-16(3)20(17(4)10-14)22-7-8-23(13-22)21-18(5)11-15(2)12-19(21)6/h7-12H,1-6H3

InChIKey

JCYWCSGERIELPG-UHFFFAOYSA-N

SMILES

N1(C=CN(C2C(C)=CC(C)=CC=2C)[C]1)C1=C(C)C=C(C)C=C1C |^3:13|

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

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

Reaction

Nucleophilic 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.

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.

1,3-BIS(2,4,6-TRIMETHYLPHENYL)IMIDAZOL-2-YLIDENE(141556-42-5)Related Product Information

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