1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride

Base Information

• Chemical Name: 1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride
• CAS No.: 141556-45-8
• Molecular Formula: C21H25ClN2
• Molecular Weight: 340.896
• Hs Code.: 29332900
• European Community (EC) Number: 627-966-1
• DSSTox Substance ID: DTXSID70370166
• Mol file: 141556-45-8.mol

Synonyms:1,3-bis(2,4,6-trimethylphenyl)imidazolium;1,3-bis(2,4,6-trimethylphenyl)imidazolium chloride;bis-TMPI cpd

Chemical Property of 1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride

Chemical Property:

• Appearance/Colour: off-white to beige powder
• Melting Point: >300 °C(lit.)
• Refractive Index: 1.5940 (estimate)
• Boiling Point: 499.2°C (rough estimate)
• PSA: 8.81000
• Density: 1.0279 (rough estimate)
• LogP: 1.60840
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Water Solubility.: Slightly soluble in water.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 340.1706265
• Heavy Atom Count: 24
• Complexity: 335

Purity/Quality:

98% ^*data from raw suppliers

1,3-Dimesitylimidazolium 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: CC1=CC(=C(C(=C1)C)N2C=C[N+](=C2)C3=C(C=C(C=C3C)C)C)C.[Cl-]
• Uses: 1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride is used as a phosphine-free ligand in various metal-catalyzed coupling reactions, often with advantageous results in difficult cases. For use in the Pd-catalyzed cross-coupling of aryl Grignards with aryl chlorides (Kumada reaction). Many examples have been recorded of the use of NHC ligands in the Suzuki coupling reaction, for examples utilizing 1,3-dimesitylimidazol-2-ylidene, in the coupling of arylboronic acids with relatively unreactive aryl chlorides.

Technology Process of 1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride

There total 10 articles about 1,3-Bis(2,4,6-trimethylphenyl)imidazolium 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: 90.0%

N,N'-bis(2,4,6-trimethylphenyl)ethanediimine (56222-36-7) + ethyl chloromethyl ether (3188-13-4) → 1,3-bis(mesityl)imidazolium chloride (141556-45-8)

Guidance literature:

In tetrahydrofuran; at 40 ℃;

DOI:10.1021/jo702720a

Reference yield: 89.3%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + N,N'-bis(2,4,6-trimethylphenyl)ethanediimine (56222-36-7) → 1,3-bis(mesityl)imidazolium chloride (141556-45-8)

Guidance literature:

With chloro-trimethyl-silane; In ethyl acetate; at 70 ℃; for 2h;

DOI:10.1039/c8dt05155k

Reference yield: 86.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + (E,E)-N1,N2-bis(2,4,6-trimethylphenyl)ethane-1,2-diimine (56222-36-7) → 1,3-bis(mesityl)imidazolium chloride (141556-45-8)

Guidance literature:

With chloro-trimethyl-silane; In ethyl acetate; at 70 ℃; for 2h;

DOI:10.1021/acs.orglett.7b01105

upstream raw materials:

N,N'-bis(2,4,6-trimethylphenyl)ethanediimine

ethyl chloromethyl ether

formaldehyd

(E,E)-N¹,N²-bis(2,4,6-trimethylphenyl)ethane-1,2-diimine

Downstream raw materials:

N,N'-di(2,4,6-trimethylphenyl)imidazoluium aquatrichloroplatinate

chloro(η⁵-cyclopentadienyl)(1,3-dimesitylimidazol-2-ylidene)nickel(II)

1-[1,3-bis(2,4,6-trimethylphenyl)imidazolium]-2,2-diphenylethenolate

Refernces

• 1、 Mandal, Tanmoy,Yadav, Sudha,Choudhury, Joyanta. "Steric effect of NHC ligands in Pd(II)–NHC-catalyzed non-directed C–H acetoxylation of simple arenes". . . Retrieved 2021/09/06.
• 2、 Kickelbick, Guido,Klein, Thomas. "Aluminum nanoparticle preparation: Via catalytic decomposition of alane adducts-influence of reaction parameters on nanoparticle size, morphology and reactivity". supporting information. p. 9820 - 9834. Retrieved 2020/07/30.