141556-45-8

Basic information

• Product Name: 1,3-BIS(2,4,6-TRIMETHYLPHENYL)IMIDAZOLIUM CHLORIDE
• Synonyms: 1,3-DIMESITYLIMIDAZOLIUM CHLORIDE;1,3-BIS(2,4,6-TRIMETHYLPHENYL)-4,5-DIHYDROIMIDAZOLIUM CHLORIDE;1,3-BIS(2,4,6-TRIMETHYLPHENYL)IMIDAZOLIUM CHLORIDE;1,3-(2,4,6-TRIMETHYLPHENYL)IMIDAZOLIUM CHLORIDE;N,N'-(2,4,6-TRIMETHYLPHENYL)DIHYDROIMADAZOLIUM CHLORIDE;1,3-BIS(2,4,6-TRIMETHYLPHENYL)IMIDAZOLI&;1,3-Bis(2,4,6-trimethylphenyl)imidazoliumchloride,min.95%;1,3-BIS-(2,4,6-TRIMETHYLPHENYL)-1H-IMIDAZOLIUM CHLORIDE
• CAS NO: 141556-45-8
• Molecular Formula: C₂₁H₂₅N₂*Cl
• Molecular Weight: 340.89
• Product Categories: API intermediates;Imidazolium Compounds;Ligands;N-Heterocyclic Carbene Ligands;Synthetic Organic Chemistry;Catalysis and Inorganic Chemistry;Chemical Synthesis;NHC Compounds;organic amine;Achiral Nitrogen;NHC
• Mol File: 141556-45-8.mol
• Article Data: 24

Chemical Properties

• Melting Point: >300 °C(lit.)
• Boiling Point: 499.2°C (rough estimate)
• Appearance: Off-white to beige/Powder
• Density: 1.0279 (rough estimate)
• Refractive Index: 1.5940 (estimate)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Water Solubility: Slightly soluble in water.
• CAS DataBase Reference: 1,3-BIS(2,4,6-TRIMETHYLPHENYL)IMIDAZOLIUM CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-BIS(2,4,6-TRIMETHYLPHENYL)IMIDAZOLIUM CHLORIDE(141556-45-8)
• EPA Substance Registry System: 1,3-BIS(2,4,6-TRIMETHYLPHENYL)IMIDAZOLIUM CHLORIDE(141556-45-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• TSCA: No
• Hazardous Substances Data: 141556-45-8(Hazardous Substances Data)

Usage

Chemical Properties

off-white to beige powder

Uses

1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride is used as a phosphine-free ligand in various metal-catalyzed coupling reactions, often with advantageous results in difficult cases. For use in the Pd-catalyzed cross-coupling of aryl Grignards with aryl chlorides (Kumada reaction). Many examples have been recorded of the use of NHC ligands in the Suzuki coupling reaction, for examples utilizing 1,3-dimesitylimidazol-2-ylidene, in the coupling of arylboronic acids with relatively unreactive aryl chlorides.

Reactions

Precursor to the 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) Palladium-catalyzed Kumada cross-coupling of aryl chlorides.(c) Ruthenium-carbene catalysts for ring-closing metathesis.(d) Suzuki coupling of aryltrimethylammonium salts.(e) Sonogashira coupling of aryl bromides.Precursor to a nucleophilic carbene that serves as catalyst.Ligand for arylation of aldehydes.Ligand for carbene catalyzed intermolecular arylation of C-H bonds.Catalyst for boron conjugate additions to cyclic and acyclic α,β-unsaturated carbonyls.Ligand for dehydrogenative cyclocondensation of aldehydes, alkynes, and dialkylsilanes.Precursor for carbene for conjugate silylation of alpha, beta-unsaturated carbonyls.

InChI:InChI=1/C21H27N2.ClH/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;/h9-13H,7-8H2,1-6H3;1H/q+1;/p-1

Upstream product

• 122-51-0 orthoformic acid triethyl ester 
• 50-00-0 formaldehyd 
• 74663-75-5 1,2-bis(2,6-diisopropylphenylimino)ethane 
• 149-73-5 trimethyl orthoformate 
• 88-05-1 2,4,6-trimethylaniline 
• 56222-36-7 N,N'-bis(2,4,6-trimethylphenyl)ethanediimine 
• 56222-36-7 (E,E)-N¹,N²-bis(2,4,6-trimethylphenyl)ethane-1,2-diimine 
• 3188-13-4 ethyl chloromethyl ether 
• 1667-04-5 2-bromomesitylene 
• 25364-44-7 N-(2,4,6-trimethylphenyl)imidazole 

Downstream Products

• 675877-56-2 1,3-bis(2,4,6-trimethylphenyl)imidazolium-2-carboxylate 
• 25050-22-0 N-(3,5-dimethylphenyl)-benzamide 
• 254972-49-1 [RuCl₂(PCy₃)(1,3-bis-(2,4,6-trimethylphenyl)-2-imidazolylidene)(3-phenyl-indenylidene)] 
• 1301549-93-8 C(CH₃)2C(CH₃)2O₂BSi(CH₃)2C₆H₅(C₃H₂N₂(C₆H₂(CH₃)3)2) 
• 1312029-25-6 IMes*CSNPh 
• 1372124-93-0 1,3-bis(mesityl)imidazolium hydrogen carbonate 
• 1382354-86-0 1,3-bis(2,4,6-trimethylphenyl)imidazolium tetraphenylborate 

Relevant articles and documents

Synthesis, characterization, electrochemical properties and catalytic reactivity of N-heterocyclic carbene-containing diiron complexes

(μ-dmedt)[Fe(CO)3]2 (I, dmedt = 2,3-butanedithiol) was chosen as the parent complex. A series of new model complexes, N-heterocyclic carbene (NHC) substituted (μ-dmedt)[Fe-Fe]-NHC (II, (μ-dmedt)[Fe(CO)2]2[IMe(CH2)2IMe], IMe = 1-methylimidazol-2-ylidene; III, {(μ-dmedt)[Fe2(CO)5]}2[IMe(CH2)2IMe]; IV, (μ-dmedt)[Fe2(CO)5]IMes, IMes = 1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene; V, (μ-dmedt)[Fe2(CO)5]IMe, IMe = 1,3-dimethylimidazol-2-ylidene) as mimics of the [Fe-Fe]-H2ase active site were synthesized from I and characterized using solution IR spectroscopy, NMR spectroscopy, elemental analysis and single-crystal X-ray diffraction. The electrochemical properties of complexes I-V, with and without the addition of HOAc, were investigated by cyclic voltammetry in the coordinating solvent CH3CN to evaluate the effects of different NHC ligands on the redox properties of the iron atoms of the series of complexes. It was concluded that all the new complexes are electrochemical catalysts for proton reduction to hydrogen. The symmetrically substituted cisoid basal/basal coordination complex II displays the most negative reduction potential owing to the stronger δ-donating ability of the NHC and the orientation of the NHC donor carbon as a result of the constraints of the bridging bidentate ligands. A new application for the [Fe-Fe]-NHC model complexes in the direct catalytic hydroxylation of benzene to phenol was also studied. Under the optimized experimental conditions (II, 0.01 mmol; benzene, 0.1 mL; CH3CN, 2.0 mL; H2O2, 6.0 mmol; 60 °C, 3 h), the maximal phenol yield was 26.7%.

Application of Quantitative 1H and 19F NMR to Organometallics

Purity assessment of organometallics is particularly important for catalytic applications. While quantitative NMR is a well-known method in pharmaceutic chemistry, the present work illustrates its usefulness for the determination of the ligands and organometallics purities using proton and fluorine NMR. This method is fast, straightforward and provides accuracy results.

Aluminum nanoparticle preparation: Via catalytic decomposition of alane adducts-influence of reaction parameters on nanoparticle size, morphology and reactivity

Al nanoparticles represent one of the most challenging classes of metal nanoparticles in synthesis and handling due to their high chemical reactivity and their affinity to oxidation. A promising wet chemical preparation route is the catalytic decomposition of alane adducts. In the current systematic study, we investigated the influence of various reaction parameters, such as precursors, catalysts, solvents, reaction temperatures, capping agents, and concentrations of the reactants on the size and morphology of the resulting Al nanoparticles. One major goal was the optimization of the reaction parameters towards short reaction times. Our studies revealed that Ti alkoxides, such as Ti(OiPr)4, are much more efficient decomposition catalysts compared to other related metal catalysts. Optimized conditions for full conversion times smaller than 15 min are temperatures between 90-100 °C and non-polar solvents such as toluene. Amine alanes containing short alkyl chains, for example H3AlNMe2Et or H3AlNEt3, were the most suitable precursors, leading to the formation of the smallest nanoparticles. The use of weakly coordinating capping agents like amines and phosphines should be preferred over the commonly employed carboxylic acids because they do not accelerate the formation of an amorphous oxide shell upon binding to the particle surface. In conclusion, the best reaction parameters for a fast synthesis of Al nanoparticles via a catalytic decomposition approach are the combination of sterically less hindered amine alanes applying a Ti catalyst in toluene solutions in the presence of amine or phosphine stabilizers at elevated temperatures.