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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

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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
Pricing and availability is not currently available.

form

powder

Quality Level

100

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."[1][2][3][4][5]

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCR7440
MKCS5662
MKCN7913
MKCN0519
MKCK9485

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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
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
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
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

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