2-Chloro-1,3-bis(2,6-diisopropylphenyl)-1H-imidazol-3-ium chloride

Base Information

• Chemical Name: 2-Chloro-1,3-bis(2,6-diisopropylphenyl)-1H-imidazol-3-ium chloride
• CAS No.: 1228185-09-8
• Molecular Formula: C27H36Cl2N2
• Molecular Weight: 459.502
• Mol file: 1228185-09-8.mol

Synonyms:IPrCl HCl;1,3-Bis(2,6-di-i-propylphenyl)-2-chloroimidazolium chloride;2-Chloro-1,3-bis(2,6-diisopropylphenyl)-1H-imidazolium Chloride;N,N′-1,3-bis(2,6-diisopropylphenyl)-2-chloroimidazolium chloride;1,3-Bis(2,6-di-i-propylphenyl)-2-chloroimidazolium chloride, 98+%;2-chloro-1,3-bis(2,6-diisopropylphenyl)-1,2-dihydroimidazol-1-ium;2-Chloro-1,3-bis(2,6-diisopropylphenyl)-1H-imidazol-3-ium chloride;2-chloro-1,3-bis[2,6-di(propan-2-yl)phenyl]imidazol-1-ium,chloride;2-Chloro-1,3-bis(2,6-diisopropylphenyl)-1H-imidazolium Chloride;1H-Imidazolium, 1,3-bis[2,6-bis(1-methylethyl)phenyl]-2-chloro-, chloride (1:1)

Chemical Property of 2-Chloro-1,3-bis(2,6-diisopropylphenyl)-1H-imidazol-3-ium chloride

Chemical Property:

• Melting Point: 283-285 °C
• PSA: 8.81000
• LogP: 4.90500
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-Chloro-1,3-bis(2,6-diisopropylphenyl)-1H-imidazolium Chloride >98.0%(T) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 2-Chloro-1,3-bis(2,6-diisopropylphenyl)imidazolium Chloride is used in the synthetic preparation aryl fluorides via fluorination of phenols by bisdiisopropylphenyldifluoroimidazolidene prepared from diisopropylaniline. This chloroimidazolium chloride is used in the deoxyfluorination of phenols. Recently, the Ritter lab used it in conjunction with 902314 and 906794 to incorporate the [18F]fluoride radiolabel site specifically into polypeptides for use with positron emission tomography (PET) imaging in the study of various biological applications.

Technology Process of 2-Chloro-1,3-bis(2,6-diisopropylphenyl)-1H-imidazol-3-ium chloride

There total 4 articles about 2-Chloro-1,3-bis(2,6-diisopropylphenyl)-1H-imidazol-3-ium chloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.0%

1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene (244187-81-3) → N,N′-1,3-bis(2,6-diisopropylphenyl)-2-chloroimidazolium chloride (1228185-09-8)

Guidance literature:

With hexachloroethane; In tetrahydrofuran; at -40 - 23 ℃; for 24h;

Reference yield: 81.0%

1,3-bis[2,6-diisopropylphenyl]imidazolium chloride (250285-32-6) → N,N′-1,3-bis(2,6-diisopropylphenyl)-2-chloroimidazolium chloride (1228185-09-8)

Guidance literature:

1,3-bis[2,6-diisopropylphenyl]imidazolium chloride; With potassium tert-butylate; In tetrahydrofuran; at 23 ℃; for 4h; Inert atmosphere;

With hexachloroethane; In tetrahydrofuran; at -40 - 23 ℃; Inert atmosphere;

DOI:10.1021/ja2048072

Reference yield:

2,6-diisopropylbenzenamine (24544-04-5) → N,N′-1,3-bis(2,6-diisopropylphenyl)-2-chloroimidazolium chloride (1228185-09-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: acetic acid / methanol; water / 10.25 h / 23 - 50 °C / Inert atmosphere

2.1: chloro-trimethyl-silane / ethyl acetate / 2.75 h / 70 °C / Inert atmosphere

3.1: potassium tert-butylate / tetrahydrofuran / 4 h / 23 °C / Inert atmosphere

3.2: -40 - 23 °C / Inert atmosphere

With chloro-trimethyl-silane; potassium tert-butylate; acetic acid; In tetrahydrofuran; methanol; water; ethyl acetate;

DOI:10.1021/ja2048072

upstream raw materials:

1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene

2,6-diisopropylbenzenamine

1,2-bis(2,6-diisopropylphenylimino)ethane

1,3-bis[2,6-diisopropylphenyl]imidazolium chloride

Downstream raw materials:

1,3-bis(2,6-diisopropylphenyl)-4-chloroimidazol-2-ylidene

Refernces

• 1、 Chen, Junting,Ritter, Tobias. "Late-stage deoxyfluorination of phenols with phenofluormix". . p. 16 - 35. Retrieved 2019/08/08.
• 2、 Fujimoto, Teppei,Becker, Fabian,Ritter, Tobias. "PhenoFluor: Practical synthesis, new formulation, and deoxyfluorination of heteroaromatics". supporting information. p. 1041 - 1044. Retrieved 2014/11/07.