Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

696307

Sigma-Aldrich

Chloro[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]copper(I)

Synonym(s):

[(iPr)CuCl], [1,3-Bis(2,6-diisopropylphenyl)imidazol-2-ylidene]copper(I) chloride

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C27H36ClCuN2
CAS Number:
578743-87-0
Molecular Weight:
487.59
MDL number:
MFCD09264276
UNSPSC Code:
12161600
PubChem Substance ID:
329761816
NACRES:
NA.22

form

powder

reaction suitability

core: copper
reagent type: catalyst

mp

>300 °C

SMILES string

CC(C)c1cccc(C(C)C)c1N2C=CN(\C2=[Cu]\Cl)c3c(cccc3C(C)C)C(C)C

InChI

1S/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

InChI key

JPUFNIIPFXQOCB-UHFFFAOYSA-M

Application

"Use for reduction of olefin and carbonyl, carbene transfer reaction, aziridination of olefins, and methyleneation of aldehydes."

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Hélène Lebel et al.
The Journal of organic chemistry, 72(1), 144-149 (2006-12-30)
(NHC)-Cu (NHC = N-heterocyclic carbene) complexes efficiently catalyzed the methylenation of a variety of aliphatic and aromatic aldehydes and ketones in the presence of trimethylsilyldiazomethane, triphenylphosphine, and 2-propanol. The copper catalysts are not only inexpensive compared to rhodium complexes, but
Barry M Trost et al.
Journal of the American Chemical Society, 128(18), 6054-6055 (2006-05-04)
New classes of nucleophiles, pyrroles, and N-methoxyamides were developed for Pd-catalyzed AAA reactions. By varying the functional groups at the 2-position of pyrroles, either regioisomer of the piperazinone is available. Using one regioisomer, the total synthesis of (+)-agelastatin A in
Kaur H. et al.
Organometallics, 23, 1157-1157 (2004)
Manuel R Fructos et al.
Journal of the American Chemical Society, 126(35), 10846-10847 (2004-09-02)
The complex IPrCuCl (1) catalyzes the transfer of the :CHCO2Et group from ethyl diazoacetate (EDA) to unsaturated and saturated substrates (olefins, amine, alcohols) with very high yields. In the absence of substrate, the complex 1 does not react with EDA
Valdas Jurkauskas et al.
Organic letters, 5(14), 2417-2420 (2003-07-05)
[reaction: see text] An N-heterocyclic carbene copper chloride (NHC-CuCl) complex (2) has been prepared and used to catalyze the conjugate reduction of alpha,beta-unsaturated carbonyl compounds. The combination of catalytic amounts of 2 and NaOt-Bu with poly(methylhydrosiloxane) (PMHS) as the stoichiometric

Articles

N-Heterocyclic Carbene-Copper Complexes

N-Heterocyclic Carbene-Copper Complexes

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service