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| | 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)-2h-imidazol-1-ium-2-ide;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 | | 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 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| |
| 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 | | Storage Class | 4.1B - Flammable solid hazardous materials | | Hazard Classifications | Eye Irrit. 2
Flam. Sol. 2
Skin Irrit. 2
STOT SE 3 |
| | 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. | | reaction suitability | reagent type: catalyst |
| | 1,3-BIS(2,4,6-TRIMETHYLPHENYL)IMIDAZOL-2-YLIDENE Preparation Products And Raw materials |
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