1,3-bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium

Base Information

• Chemical Name: 1,3-bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium
• CAS No.: 258278-25-0
• Molecular Formula: C₂₇H₃₉N₂*Cl
• Molecular Weight: 427.073
• Hs Code.: 29332900
• DSSTox Substance ID: DTXSID30948724
• Nikkaji Number: J1.215.215I,J1.554.190C
• Wikidata: Q72445060
• Mol file: 258278-25-0.mol

Synonyms:1,3-bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium;282109-82-4;SCHEMBL819459;DTXSID30948724;SB66712;FT-0747133;1,3-Bis(2,6-diisopropylphenyl)-1-imidazoline-1-ium;1,3-Bis(2,6-diisopropylphenyl)imidazolidine-2-ylium;1,3-Bis[2,6-di(propan-2-yl)phenyl]-4,5-dihydro-1H-imidazol-3-ium

Chemical Property of 1,3-bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium

Chemical Property:

• Appearance/Colour: White to yellow crystalline powder
• Melting Point: 289-293 °C(lit.)
• PSA: 6.25000
• LogP: 4.40050
• Storage Temp.: Inert atmosphere,Room Temperature
• Sensitive.: air sensitive
• Solubility.: soluble in Methanol
• XLogP3: 7.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 6
• Exact Mass: 391.311324253
• Heavy Atom Count: 29
• Complexity: 467

Purity/Quality:

98% ^*data from raw suppliers

1,3-Bis-(2,6-diisopropylphenyl)imidazolinium chloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)C1=C(C(=CC=C1)C(C)C)N2CC[N+](=C2)C3=C(C=CC=C3C(C)C)C(C)C
• Uses: Employed in an efficient, one-pot synthesis of N-heterocyclic carbene-allylpalladium complexes.

Technology Process of 1,3-bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium

There total 16 articles about 1,3-bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium 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: 99.0%

1,3-bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazolium tetrafluoroborate → 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride (258278-25-0)

Guidance literature:

With Dowex 1x4-50 anion exchange resin, chloride form; In methanol; water;

DOI:10.1039/c0cc03367g

Reference yield: 91.0%

1,2-dichloro-ethane (107-06-2,52399-93-6) + N,N'-di(2,6-diisopropylphenyl)formamidine (1176938-29-6,581776-24-1) → 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride (258278-25-0)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; at 120 ℃; for 36h;

DOI:10.1021/ol800628a

Reference yield: 72.0%

orthoformic acid triethyl ester (122-51-0) + N,N'-bis-(2,6-diisopropylphenylamino)ethane dihydrochloride → 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride (258278-25-0)

Guidance literature:

at 145 ℃; for 0.0833333h; microwave irradiation;

DOI:10.1055/s-2006-932455

upstream raw materials:

orthoformic acid triethyl ester

N,N'-bis(2,6-diisopropylphenyl)ethane-1,2-diamine

2,6-diisopropylbenzenamine

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

Downstream raw materials:

1,3-bis[2,6-di(propan-2-yl)phenyl]-1,3-dihydro-2H-imidazol-2-one

1,3-bis(2,6-diisopropylphenyl)-1H-imidazole-2(3H)-thione

chloro[1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene]copper(I)

Refernces

• 1、 Li, Dazhi,Ollevier, Thierry. "Mechanism studies of oxidation and hydrolysis of Cu(I)–NHC and Ag–NHC in solution under air". supporting information. . Retrieved 2019/11/29.
• 2、 Beillard, Audrey,Bantreil, Xavier,Métro, Thomas-Xavier,Martinez, Jean,Lamaty, Frédéric. "Mechanochemistry for facilitated access to N,N-diaryl NHC metal complexes". supporting information. p. 1057 - 1063. Retrieved 2017/02/10.