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696188

1,3-Bis(2,4,6-trimethylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene

Name: 1,3-Bis(2,4,6-trimethylphenyl)-1,3-dihydro-2<I>H</I>-imidazol-2-ylidene
Brand: ALDRICH

97%

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Synonym(s):

1,3-Bis(2,4,6-trimethylphenyl)imidazol-2-ylidene

Empirical Formula (Hill Notation):

C₂₁H₂₄N₂

CAS Number:

141556-42-5

Molecular Weight:

304.43

MDL number:

MFCD09265338

PubChem Substance ID:

329761806

NACRES:

NA.22

Quality Level

100

Assay

97%

form

powder

reaction suitability

reagent type: catalyst

mp

140 °C

storage temp.

−20°C

SMILES string

Cc1cc(C)c(N2[C]N(C=C2)c3c(C)cc(C)cc3C)c(C)c1

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

InChI key

JCYWCSGERIELPG-UHFFFAOYSA-N

Related Categories

NHC Ligands & Complexes

Application

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.

Pictograms

GHS02,GHS07

Signal Word

Warning

Hazard Statements

H228 - H315 - H319 - H335

Precautionary Statements

P210 - P302 + P352 - P305 + P351 + P338

Hazard Classifications

Eye Irrit. 2 - Flam. Sol. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

4.1B - Flammable solid hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Olefin metathesis-active ruthenium complexes bearing a nucleophilic carbene ligand

Huang J, et al.

Journal of the American Chemical Society, 121(12), 2674-2678 (1999)

Hydrogenation of (Hetero) aryl Boronate Esters with a Cyclic (Alkyl)(amino) carbene-Rhodium Complex: Direct Access to cis-Substituted Borylated Cycloalkanes and Saturated Heterocycles

Ling L, et al.

Angewandte Chemie (International Edition in English), 58(20), 6554-6558 (2019)

Suzuki- Miyaura cross-coupling reactions mediated by palladium/imidazolium salt systems

Grasa GA, et al.

Organometallics, 21(14), 2866-2873 (2002)

Normal-to-Abnormal NHC Rearrangement of Al(III) , Ga(III) , and In(III) Trialkyl Complexes: Scope, Mechanism, Reactivity Studies, and H2 Activation.

Gilles Schnee et al.

Chemistry (Weinheim an der Bergstrasse, Germany), 21(49), 17959-17972 (2015-10-21)

The present contribution reports experimental and theoretical mechanistic investigations on a normal-to-abnormal (C2-to-C4-bonded) NHC rearrangement processes occurring with bulky group 13 metal NHC adducts, including the scope of such a reactivity for Al compounds. The sterically congested adducts (nItBu)MMe3 (nItBu=1,3-di-tert-butylimidazol-2-ylidene;

Mixture of Azolium Tetraphenylborate with Isopropylthioxanthone: A New Class of N-Heterocyclic Carbene (NHC) Photogenerator for Polyurethane, Polyester, and ROMP Polymers Synthesis.

Thi Kim Hoang Trinh et al.

Chemistry (Weinheim an der Bergstrasse, Germany), 25(39), 9242-9252 (2019-04-26)

In the search of smarter routes to control the conditions of N-heterocyclic carbene (NHCs) formation, a two-component air-stable NHC photogenerating system is reported. It relies on the irradiation at 365 nm of a mixture of 2-isopropylthioxanthone (ITX) with 1,3-bis(mesityl)imidazoli(ni)um tetraphenylborate. The

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