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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:
258278-25-0
Molecular Weight:
427.06
UNSPSC Code:
12352005
PubChem Substance ID:
24884212
NACRES:
NA.22
MDL number:
MFCD07369796
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Product Name

1,3-Bis-(2,6-diisopropylphenyl)imidazolinium chloride, 97%

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

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.
N-Heterocyclic Carbene Ligands
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.

pictograms

Exclamation mark
GHS07

signalword

Warning

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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Certificates of Analysis (COA)

Lot/Batch Number
MKCN0174
MKCH7463
MKCB3838
MKBV9204V
MKBP0376V

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Articles

N-杂环卡宾（NHC）配体

随着金属络合物催化的未活化底物的交叉偶联反应领域的快速进展，通过引入大量的非手性和手性膦配体化合物库，已变革了化学市场。

N-Heterocyclic Carbene Ligands

A wide range of NHC ligands are commonly available which exhibit high activities.

1-tBu-Indenyl Supported Palladium Precatalysts for Cross-Coupling

The Hazari group has developed an improved palladium precatalyst scaffold for a wide range of cross-coupling reactions

View All Articles
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
Synlett, 366-366 (2006)
Palladium-(N-heterocyclic carbene) hydrogenation catalysts.
Jeroen W Sprengers et al.
Angewandte Chemie (International ed. in English), 44(13), 2026-2029 (2005-02-24)
View All Related Papers

Global Trade Item Number

SKUGTIN
656623-1G04061832733296
656623-5G04061832733302