656623

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

97%

• Synonym(s): N,N′-(2,6-Diisopropylphenyl)dihydroimidazolium chloride
• 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

Properties

• 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

Description

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.

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H315,H319,H335
• Precautionary Statements: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• 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