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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

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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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
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
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

Articles

N-Heterocyclic Carbene-Copper Complexes

N-Heterocyclic Carbene-Copper Complexes

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    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
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      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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