258278-25-0

Basic information

• Product Name: 1,3-BIS(2,6-DIISOPROPYLPHENYL)-IMIDAZOLIDINIUM-CHLORIDE
• Synonyms: 1,3-BIS(2,6-DIISOPROPYLPHENYL)-IMIDAZOLIDINIUM-CHLORIDE;1,3-BIS[2,6-BIS(1-METHYLETHYL)PHENYL]-4,5-DIHYDRO-1H-IMIDAZOLIUM CHLORIDE;1,3-Bis-(2,6-diisopropyl-phenyl)-imidazolidin-1-ium chloride;SIPr.HCl;1,3-Bis-(2,6-diisopropylphenyl)imidazolidinium;1,3-Bis(2,6-diisopropylphenyl)imidazolidiniumchloride,90%;1,3-Bis-(2,6-diisopropyl-phenyl)-4,5-dihydro-3H-imidazol-1-ium;1,3-Bis-(2,6-diisopropylphenyl)imidazolinium chloride,N,N′-(2,6-Diisopropylphenyl)dihydroimidazolium chloride
• CAS NO: 258278-25-0
• Molecular Formula: C27H41ClN2
• Molecular Weight: 429.08
• Product Categories: N-Heterocyclic Carbene Ligands;Ligands;Synthetic Organic Chemistry;Achiral Nitrogen;NHC
• Mol File: 258278-25-0.mol
• Article Data: 14

Chemical Properties

• Melting Point: 289-293 °C(lit.)
• Appearance: White to yellow/Crystalline Powder
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: soluble in Methanol
• Sensitive: air sensitive
• CAS DataBase Reference: 1,3-BIS(2,6-DIISOPROPYLPHENYL)-IMIDAZOLIDINIUM-CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-BIS(2,6-DIISOPROPYLPHENYL)-IMIDAZOLIDINIUM-CHLORIDE(258278-25-0)
• EPA Substance Registry System: 1,3-BIS(2,6-DIISOPROPYLPHENYL)-IMIDAZOLIDINIUM-CHLORIDE(258278-25-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• TSCA: No
• Hazardous Substances Data: 258278-25-0(Hazardous Substances Data)

Usage

Chemical Properties

White to yellow crystalline powder

Uses

Employed in an efficient, one-pot synthesis of N-heterocyclic carbene-allylpalladium complexes.

InChI:InChI=1/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

Upstream product

• 24544-04-5 2,6-diisopropylbenzenamine 
• 107-06-2 1,2-dichloro-ethane 
• 122-51-0 orthoformic acid triethyl ester 
• 74663-75-5 1,2-bis(2,6-diisopropylphenylimino)ethane 
• 134030-22-1 N,N'-bis(2,6-diisopropylphenyl)ethane-1,2-diamine 
• 64-18-6 formic acid 
• 1176938-29-6 N,N'-di(2,6-diisopropylphenyl)formamidine 

Downstream Products

• 1350747-57-7 [1,3-bis(2,6-diisopropylphenyl)imidazolinium chloride][FeCl(N(SiMe₃)2)2] 
• 1060651-05-9 1,3-bis[2,6-di(propan-2-yl)phenyl]-1,3-dihydro-2H-imidazol-2-one 
• 1311297-12-7 1,3-bis(2,6-diisopropylphenyl)-1H-imidazole-2(3H)-thione 
• 578743-87-0 chloro[1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene]copper(I) 
• 1447721-12-1 1,3-bis-(2,6-diisopropylphenyl)imidazolinium iodide 
• 1392811-06-1 1,3-bis[(2,6-diisopropyl)-4-nitrophenyl]imidazolinium chloride 

Relevant articles and documents

Application of Quantitative 1H and 19F NMR to Organometallics

Purity assessment of organometallics is particularly important for catalytic applications. While quantitative NMR is a well-known method in pharmaceutic chemistry, the present work illustrates its usefulness for the determination of the ligands and organometallics purities using proton and fluorine NMR. This method is fast, straightforward and provides accuracy results.

Synthesis of Imidazolidinone, Imidazolone, and Benzimidazolone Derivatives through Oxidation Using Copper and Air

A new synthetic method of urea derivatives using copper and air was developed. These mild conditions provided moderate to very good yields for 15 examples (53-93%), while low yields were obtained with sterically hindered substrates (3 examples). The reaction was found to go through an in situ generated copper-N-heterocyclic carbene, which was then oxidized into cyclic urea derivatives possessing alkyl, benzyl, aryl, hydroxy, Boc-protected, and tertiary amine groups.

Oxygen-atom insertion of NHCecopper complex: The source of oxygen from N, N-dimethylformamide

An unprecedented protocol for oxygen-atom insertion reaction of NHCecopper complexes has been developed by employing N,N-dimethylformamide as the oxygen source, which allows the preparation of imidazolinones from carbene complexes and decodes one of the m