656623
1,3-Bis-(2,6-diisopropylphenyl)imidazolinium chloride
97%, solid
Synonym(s):
N,N′-(2,6-Diisopropylphenyl)dihydroimidazolium chloride
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About This Item
Empirical Formula (Hill Notation):
C27H39ClN2
CAS Number:
Molecular Weight:
427.06
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22
MDL number:
Product Name
1,3-Bis-(2,6-diisopropylphenyl)imidazolinium chloride, 97%
Quality Level
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
Application
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 in an efficient, one-pot synthesis of N-heterocyclic carbene-allylpalladium complexes.
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.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
ppe
dust mask type N95 (US), Eyeshields, Gloves
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NHC-catalyzed ring expansion of oxacycloalkane-2-carboxaldehydes: a versatile synthesis of lactones.
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
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)
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