181422-81-1

Basic information

• Product Name: 2H-Imidazol-2-ylidene, 1,3-dicyclohexyl-1,3-dihydro-
• CAS NO: 181422-81-1
• Molecular Formula: C15H24N2
• Molecular Weight: 232.369
• Mol File: 181422-81-1.mol

Chemical Properties

• CAS DataBase Reference: 2H-Imidazol-2-ylidene, 1,3-dicyclohexyl-1,3-dihydro-(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-Imidazol-2-ylidene, 1,3-dicyclohexyl-1,3-dihydro-(181422-81-1)
• EPA Substance Registry System: 2H-Imidazol-2-ylidene, 1,3-dicyclohexyl-1,3-dihydro-(181422-81-1)

Safety Data

• Hazardous Substances Data: 181422-81-1(Hazardous Substances Data)

Upstream product

• 181422-72-0 1,3-dicyclohexyl-1H-imidazol-3-ium chloride 

Relevant articles and documents

Highly efficient trialkylsilylcyanation of aldehydes, ketones and imines catalyzed by a nucleophilic N-heterocyclic carbene

The synthetic utility of N-heterocyclic carbenes was demonstrated by the trialkylsilylcyanation of aldehydes, ketones and imines. In the presence of a catalytic amount of 3a, the reactions with Me3SiCN proceeded smoothly to give the corresponding cyanohydrin trimethylsilyl ethers or amino nitrile derivatives in good to excellent yields.

Catalytic activity of N-heterocyclic carbenes in ring opening polymerization of cyclic siloxanes

Taking advantage of the strong nucleophilic properties of N-heterocyclic carbene (NHC), the efficient catalytic ring opening polymerization (ROP) of cyclotetrasiloxane D4 was achieved under mild conditions.

A closer look at the reactivity between N-heterocyclic carbenes and fluoroalkenes

The fundamental reactivity leading to N-heterocyclic fluoroalkene adducts is explored in detail, featuring a total of 15 N-heterocyclic carbenes (NHCs) with various electronic and steric environments. The activity of these carbenes towards tetrafluoroethylene (TFE), hexafluoropropene (HFP), trifluoroethylene (HTFE) and vinylidene fluoride (VDF) is assessed in THF and toluene. Attempts were made to correlate the observed reactivity with electronic (Tolman Electronic Parameters) and steric (% buried volume) parameters unique to each NHC, but a trend has yet to be fully determined. However, the unique steric constraints of a cyclic (alkyl)(amino)carbene (CAAC) were shown to modify the initial point of nucleophilic attack on HTFE, providing selective transformation to a different adduct than has been observed to date with all reactions involving this fluoroalkene.

Modular Bidentate Hybrid NHC-Thioether Ligands for the Stabilization of Palladium Nanoparticles in Various Solvents

The synthesis of four different bidentate hybrid NHC-thioether ligands is presented. The corresponding palladium nanoparticles are stable in various solvents, depending on the ligand used, and show high chemoselectivity in the hydrogenation of olefins. The solubility of the nanoparticles can be switched multiple times depending on the pH value of the solvent. XPS analysis (which shows a subtle shift in the binding energy) was identified as a convenient tool to establish the binding mode of NHC ligands.

Method for preparing carbene in solution, novel stable form of carbene obtained in particular by means of said method, and uses thereof in catalysis

The invention relates to a method for preparing carbene by means of deprotonation of a precursor salt using a strong base. A purpose of the invention is to enhance the synthesis of carbenes, i.e. to simplify same, to make said synthesis more economical an

Molybdenum Imido Alkylidene N-Heterocyclic Carbene Complexes: Structure–Productivity Correlations and Mechanistic Insights

The syntheses and single-crystal X-ray structures of a series of Mo–imido alkylidene N-heterocyclic carbene (NHC) complexes (1–15) and of the first complexes containing bidentate NHC-phenolate ligands (16–18) are reported. Mo(N-2,6-Me2-C6H3)((1-R-phenethyl)-3-mesitylimidazolidin-2-ylidene)(CHR)(OTf)2 (R=CMe2Ph, 1) is the first enantiomerically pure Mo–imido alkylidene NHC catalyst. With [Mo(N-2,6-Me2-C6H3)(IMes)(CHR)(CH3CN)(OTf)(CH3CN)+ B(ArF)4?] (7), turnover numbers up to 545 000 were achieved in the homometathesis (HM) of 1-octene and 1-nonene (≤95 percent E). With 7 and 1-nonene, a turnover frequency (TOF4 min) of 8860 min?1 was determined. Productivity and E/Z-selectivity were correlated with catalyst structure. For 1, Mo(N-3,5-Me2-C6H3)(IMesH2)(CHR)(OTf)2 (9) and Mo(N-3,5-Me2-C6H3)(IMes)(CHR)(OTf)2 (10), productivity was correlated with the coalescence temperature of the two triflates, determined by variable-temperature 19F NMR spectroscopy. The square-planar conformer is postulated to be the most relevant for the catalyst activation.

METHOD FOR PREPARING CARBENE IN SOLUTION, NOVEL STABLE FORM OF CARBENE OBTAINED IN PARTICULAR BY MEANS OF SAID METHOD, AND USES THEREOF IN CATALYSIS

The invention relates to a method for preparing carbene by means of deprotonation of a precursor salt using a strong base. A purpose of the invention is to enhance the synthesis of carbenes, i.e. to simplify same, to make said synthesis more economical an

N-Formylation of amines by methanol activation

The homogeneous catalyzed dehydrogenation of methanol in a synthetically valuable cross-coupling reaction was achieved. By the use of a simple ruthenium-N-heterocyclic carbene complex, MeOH and primary or secondary amines can be converted into formamides.

N-Heterocyclic Carbenes: Generation under Mild Conditions and Formation of Group 8-10 Transition Metal Complexes Relevant to Catalysis

Stable mono- and dicarbene adducts of late transition metals are readily accessible either by reaction of imidazolium salts with metal complexes bearing basic ligands, or by the cleavage of chloro- and acetato-bridged dinuclear metal complexes with the fr