578743-87-0

Basic information

• Product Name: CHLORO[1,3-BIS(2,6-DI-I-PROPYLPHENYL)IMIDAZOL-2-YLIDENE]COPPER(I)
• Synonyms: CHLORO[1,3-BIS(2,6-DI-I-PROPYLPHENYL)IMIDAZOL-2-YLIDENE]COPPER(I);Chloro[1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene]copper(I),98%;[1,3-Bis(2,6-diisopropylphenyl)imidazol-2-ylidene]copper(I) chloride;Chloro[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]copper(I);[1,3-Bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene](chloro)copper;[1,3-Bis(2,6-diisopropylphenyl)imidazol-2-ylidene]copper chloride;Chloro[1,3-bis(2,6-diisopropylphenyl)iMidazol-2-ylidene]copp;[(iPr)CuCl]
• CAS NO: 578743-87-0
• Molecular Formula: C₂₇H₃₆ClCuN₂
• Molecular Weight: 487.58714
• Product Categories: Catalysis and Inorganic Chemistry;Chemical Synthesis;Copper;organometallic complex;Cu
• Mol File: 578743-87-0.mol
• Article Data: 46

Chemical Properties

• Melting Point: >300 °C
• Appearance: white/Powder
• Storage Temp.: Inert atmosphere,Room Temperature
• Sensitive: air sensitive
• CAS DataBase Reference: CHLORO[1,3-BIS(2,6-DI-I-PROPYLPHENYL)IMIDAZOL-2-YLIDENE]COPPER(I)(CAS DataBase Reference)
• NIST Chemistry Reference: CHLORO[1,3-BIS(2,6-DI-I-PROPYLPHENYL)IMIDAZOL-2-YLIDENE]COPPER(I)(578743-87-0)
• EPA Substance Registry System: CHLORO[1,3-BIS(2,6-DI-I-PROPYLPHENYL)IMIDAZOL-2-YLIDENE]COPPER(I)(578743-87-0)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 578743-87-0(Hazardous Substances Data)

Usage

Description

CHLORO[1,3-BIS(2,6-DI-I-PROPYLPHENYL)IMIDAZOL-2-YLIDENE]COPPER(I) is an organometallic compound that features a copper(I) center coordinated to an imidazol-2-ylidene ligand. This complex is characterized by its unique structure and reactivity, making it a versatile catalyst in various chemical reactions.

Uses

Used in Pharmaceutical Industry:
CHLORO[1,3-BIS(2,6-DI-I-PROPYLPHENYL)IMIDAZOL-2-YLIDENE]COPPER(I) is used as a catalyst for the reduction of olefins and carbonyl compounds, which are key steps in the synthesis of various pharmaceutical compounds. Its ability to facilitate these reactions with high selectivity and efficiency makes it a valuable tool in the development of new drugs.
Used in Chemical Synthesis:
In the field of chemical synthesis, CHLORO[1,3-BIS(2,6-DI-I-PROPYLPHENYL)IMIDAZOL-2-YLIDENE]COPPER(I) is employed as a catalyst for carbene transfer reactions, aziridination of olefins, and methyleneation of aldehydes. These reactions are essential for the construction of complex molecular structures, and the use of this copper complex allows for greater control over the reaction outcomes, leading to the synthesis of a wide range of organic compounds with potential applications in various industries.
Used in Material Science:
CHLORO[1,3-BIS(2,6-DI-I-PROPYLPHENYL)IMIDAZOL-2-YLIDENE]COPPER(I) can also be utilized in the development of new materials, such as polymers and coordination compounds, due to its unique catalytic properties. Its ability to participate in various chemical reactions can lead to the creation of novel materials with enhanced properties, such as improved stability, reactivity, or selectivity, which can be applied in various technological applications.

Reaction

Catalyst for the aziridination of olefins. Mild catalyst, superior to CuCl, in the methylenetriphenylphosphorane methyleneation of aldehydes and ketones. Copper(I) catalyzed alkylation of aryl and alkenylsilanes. Copper-catalyzed formal methylative and hydrogenative carboxylation of alkynes with carbon dioxide. Regioselective copper-catalyzed carboxylation of allylboronates with carbon dioxide. Carboxylation of organoboronic esters with potassium methyl carbonate under copper catalysis. Catalytic anti-Markovnikov hydrobromination of alkynes. Copper-catalyzed borylative cross-coupling of allenes and imines.

InChI:InChI=1/C27H36N2.ClH.Cu/c1-18(2)22-11-9-12-23(19(3)4)26(22)28-15-16-29(17-28)27-24(20(5)6)13-10-14-25(27)21(7)8;;/h9-16,18-21H,1-8H3;1H;/q;;+1/p-1/rC27H36ClCuN2/c1-17(2)21-11-9-12-22(18(3)4)25(21)30-15-16-31(27(30)29-28)26-23(19(5)6)13-10-14-24(26)20(7)8/h9-20H,1-8H3

Upstream product

• 250285-32-6 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride 
• 7647-01-0 hydrogenchloride 
• 12775-96-1 copper 
• 917604-39-8 1,3-bis(2,6-diisopropylphenyl)imidazolylium-2-carboxylate 
• 244187-81-3 1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene 
• 258278-25-0 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride 
• 74663-75-5 1,2-bis(2,6-diisopropylphenylimino)ethane 
• 1317-39-1 copper(I) oxide 
• 106-43-4 para-chlorotoluene 
• 55718-76-8 2-chloro-1,3,2-benzodioxaborole 
• 73183-34-3 bis(pinacol)diborane 
• 81656-21-5 2-chloro-1,3,2-dioxa(BCH₂CMe₂CH₂) 

Downstream Products

• 94647-81-1 2-tert-butoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1228216-70-3 C₂₇H₃₆ClN₂⁽¹⁺⁾ 

Relevant articles and documents

Cleavage of X-H bonds (X = N, O, or C) by copper(I) alkyl complexes to form monomeric two-coordinate copper(I) systems

The monomeric copper(I) alkyl complexes (IPr)Cu(R) [R = Me or Et; IPr= 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene] react with substrates that possess N-H, O-H, and acidic C-H bonds to form monomeric systems of the type (IPr)Cu(X) (X = anilido, phenoxide, ethoxide, phenylacetylide, or N-pyrrolyl) and methane or ethane. Solid-state X-ray crystal structures of the anilido, ethoxide, and phenoxide complexes confirm that they are monomeric systems. Experimental studies on the reaction of (IPr)Cu(Me) and aniline to produce (IPr)Cu(NHPh) suggest that a likely reaction pathway is coordination of aniline to Cu(I) followed by proton transfer to produce methane and the copper(I) anilido complex.

(NHC) CuI (NHC = N-Heterocyclic carbene) complexes as efficient catalysts for the reduction of carbonyl compounds

The hydrosilylation of various ketones is mediated by an imidazolium salt/Cu(I) salt system or by a well-defined (NHC)CuCl (NEC = N-heterocydic carbene) catalyst precursor system. Reactions are conducted at room temperature. The synthesis and characterization of well-defined (NHC)CuCl complexes are described.

Simple and versatile selective synthesis of neutral and cationic copper(i) N-heterocyclic carbene complexes using an electrochemical procedure

An electrochemical approach for the preparation of copper(i) N-heterocyclic carbene complexes has been developed to include a diverse range of ligand precursors. Importantly, the method is effective for a ligand precursor that contains several acidic prot

Microwave-assisted synthesis of (N-heterocyclic carbene)MCl complexes of group 11 metals

The use of microwave heating for the synthesis of (N-heterocyclic carbene)-bearing complexes of Cu, Ag and Au allows for a drastic reduction of the reaction times required by conventional heating, while affording comparable or better yields of the desired complexes. Copyright

Addition of N-H and O-H bonds of amines and alcohols to electron-deficient olefins catalyzed by monomeric copper(I) systems: Reaction scope, mechanistic details, and comparison of catalyst efficiency

Monomeric copper(I) amido, alkoxide, and aryloxide complexes catalyze the addition of N-H and O-H bonds of amines and alcohols, respectively, to electron-deficient olefins. The ancillary ligands of the active catalysts include the N-heterocyclic carbene (

Simplified preparation of copper(I) NHCs using aqueous ammonia

The use of aqueous ammonia as a coordinating and basic reagent for the metalation of imidazol(in)ium salts derived from (S)IPr and (S)IMes with simple inorganic copper precursors is reported. The synthesis of copper carbene complexes was performed using aqueous/alcoholic media in mild conditions (room temperature to 60 C) with short reaction times. Heteroleptic bromide and iodide complexes could be prepared efficiently for (S)IPr, while chloride complexes were easily accessible for SIMes and (S)IPr. Ammonia also allowed the efficient synthesis of homoleptic [Cu(NHC)2](Y) (NHC = (S)IMes; Y = PF 6, BF4) species by a variant procedure in ethanol.

Continuous Flow Synthesis of Metal–NHC Complexes**

The use of weak bases and mild conditions is currently the most sustainable and attractive synthetic approach for the preparation of late-transition metal complexes, some of which are widely used in catalysis, medicinal chemistry and materials science. Herein, the use of cuprate, aurate or palladate species for a continuous flow preparation of CuI, AuI and PdII-NHC complexes is reported. All reactions examined proceed under extremely mild conditions and make use of technical grade acetone as solvent. The scalability of the process was exemplified in a multigram-scale synthesis of [Cu(IPr)Cl].

Excited-State Copper Catalysis for the Synthesis of Heterocycles

Heterocycles are one of the largest groups of organic moieties with significant medicinal, chemical, and industrial applications. Herein, we report the discovery and development of visible-light-induced, synergistic excited-state copper catalysis using a combination of Cu(IPr)I as a catalyst and rac-BINAP as a ligand, which produces more than 10 distinct classes of heterocycles. The reaction tolerates a broad array of functional groups and complex molecular scaffolds, including derivatives of peptides, natural products, and marketed drugs. Preliminary mechanistic investigation suggests in situ generations of [Cu(BINAP)2]+ and [Cu(IPr)2]+ catalysts that work cooperatively under visible-light irradiation to facilitate catalytic carbo-aroylation of unactivated alkenes, affording a wide range of useful heterocycles.

Copper-catalysed synthesis of α-alkylidene cyclic carbonates from propargylic alcohols and CO2

We report a N-heterocyclic carbene copper(i) complex-catalysed formal cycloaddition between readily available propargylic alcohols and carbon dioxide at room temperature. By using the combination of a sterically demandingBPDPrCuCl complex (BPDPr = 1,3-bis(2,6-diisopropylphenyl)-1,3-diazonine-2-ylidene) and CsF, as catalytic system, primary propargylic alcohols are efficiently converted to the corresponding α-alkylidene cyclic carbonates. Gram scale (up to 89% yield) and reusability experiments (74% global yield, turnover number value = 103) showcase the robustness of the catalytic system. This practically simple protocol also tolerates secondary and tertiary propargylic alcohols under CO2at atmospheric pressure, enabling the direct synthesis of substituted and unsubstituted α-alkylidene cyclic carbonates at room temperature.