Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

656623

Sigma-Aldrich

1,3-Bis-(2,6-diisopropylphenyl)imidazolinium chloride

97%

Synonym(s):

N,N′-(2,6-Diisopropylphenyl)dihydroimidazolium chloride

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

About This Item

Empirical Formula (Hill Notation):
C27H39ClN2
CAS Number:
258278-25-0
Molecular Weight:
427.06
MDL number:
MFCD07369796
UNSPSC Code:
12352005
PubChem Substance ID:
24884212
NACRES:
NA.22

Quality Level

100

Assay

97%

form

solid

reaction suitability

reagent type: ligand

mp

289-293 °C (lit.)

SMILES string

[Cl-].CC(C)c1cccc(C(C)C)c1N2CC[N+](=C2)c3c(cccc3C(C)C)C(C)C

InChI

1S/C27H39N2.ClH/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;/h9-14,17-21H,15-16H2,1-8H3;1H/q+1;/p-1

InChI key

LWPXTYZKAWSRIP-UHFFFAOYSA-M

Related Categories

Application

N-Heterocyclic Carbene Ligands
The palladium/1,3-bis-(2,6-diisopropylphenyl)imidazolinium chloride (IPr·HCl) system can efficiently catalyze the Suzuki-Miyaura coupling of aryl chlorides with aryl boronic acids.
Used as a precursor to the free carbene 1,3-bis(2,6-diisopropylphenyl)-2-imidazolidinylidene, and also used as an in situ formed catalyst in a variety of reactions, e.g. amination, Heck coupling reaction, the ring-opening metathesis polymerization (ROMP), hydrogenation.
Used in an efficient, one-pot synthesis of N-heterocyclic carbene-allylpalladium complexes.

related product

Product No.
Description
Pricing

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

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

Suzuki?Miyaura cross-coupling of aryl and alkyl halides using palladium/imidazolium salt protocols.
Arentsen K, et al.
Tetrahedron Letters, 45(17), 3511-3515 (2004)
Li Wang et al.
Organic letters, 11(4), 891-893 (2009-02-10)
Imidazolinium-derived carbenes catalyze the ring-expansion lactonization of oxacycloalkane-2-carboxaldehydes. A variety of functionalized five-, six-, and seven-membered lactones can be formed efficiently under mild reaction conditions. The success of this new method for the construction of lactones is highly influenced by
Merritt B Andrus et al.
Organic letters, 4(12), 2079-2082 (2002-06-07)
[reaction: see text] Catalyst formed from N,N-bis(2,6-diisopropylphenyl)dihydroimidazolium chloride and palladium(II) acetate (2 mol %) was used, without added base, to efficiently produce Heck coupled products with olefins and aryl diazonium tetrafluoroborate substrates. The reactions were performed at room temperature, giving
Palladium-(N-heterocyclic carbene) hydrogenation catalysts.
Jeroen W Sprengers et al.
Angewandte Chemie (International ed. in English), 44(13), 2026-2029 (2005-02-24)
Synlett, 366-366 (2006)

Articles

N-Heterocyclic Carbene (NHC) Ligands

Metal complex-catalyzed cross-coupling reactions of unactivated substrates introduce diverse phosphine ligands in chemical marketplace.

N-Heterocyclic Carbene (NHC) Ligands

Metal complex-catalyzed cross-coupling reactions of unactivated substrates introduce diverse phosphine ligands in chemical marketplace.

N-Heterocyclic Carbene (NHC) Ligands

Metal complex-catalyzed cross-coupling reactions of unactivated substrates introduce diverse phosphine ligands in chemical marketplace.

N-Heterocyclic Carbene (NHC) Ligands

Metal complex-catalyzed cross-coupling reactions of unactivated substrates introduce diverse phosphine ligands in chemical marketplace.

See All

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