Cas no 866926-59-2 (1H-Imidazolium,1-[2,6-bis(1-methylethyl)phenyl]-4,5-dihydro-3-(2,4,6-trimethylphenyl)-,chloride)

1H-Imidazolium,1-[2,6-bis(1-methylethyl)phenyl]-4,5-dihydro-3-(2,4,6-trimethylphenyl)-,chloride is a sterically hindered N-heterocyclic carbene (NHC) precursor with a chloride counterion. Its bulky substituents, including isopropyl and mesityl groups, enhance stability and prevent unwanted side reactions, making it suitable for catalytic applications. The compound is particularly useful in transition-metal catalysis, where it serves as a robust ligand precursor to improve reaction selectivity and efficiency. Its structural rigidity and electron-donating properties contribute to high thermal stability and reactivity control in demanding synthetic conditions. This imidazolium salt is commonly employed in organometallic chemistry, polymerization, and cross-coupling reactions, offering consistent performance in both academic and industrial settings.
1H-Imidazolium,1-[2,6-bis(1-methylethyl)phenyl]-4,5-dihydro-3-(2,4,6-trimethylphenyl)-,chloride structure
866926-59-2 structure
Product Name:1H-Imidazolium,1-[2,6-bis(1-methylethyl)phenyl]-4,5-dihydro-3-(2,4,6-trimethylphenyl)-,chloride
CAS No:866926-59-2
MF:C24H33ClN2
MW:384.985225439072
MDL:MFCD17018754
CID:660884
PubChem ID:24884708
Update Time:2025-05-28

1H-Imidazolium,1-[2,6-bis(1-methylethyl)phenyl]-4,5-dihydro-3-(2,4,6-trimethylphenyl)-,chloride Chemical and Physical Properties

Names and Identifiers

    • 1H-Imidazolium,1-[2,6-bis(1-methylethyl)phenyl]-4,5-dihydro-3-(2,4,6-trimethylphenyl)-,chloride
    • 1-(2,6-Diisopropylphenyl)-3-(2,4,6-triMethylphenyl)-4,5-dihydroiMidazoliuM chloride
    • 1-[2,6-di(propan-2-yl)phenyl]-3-(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-3-ium,chloride
    • 3-[2,6-Bis(1-methylethyl)phenyl]-4,5-dihydro-1-(2,4,6-trimethylphenyl)-1H-imidazolium chloride
    • 1H-Imidazolium, 1-[2,6-bis(1-methylethyl)phenyl]-4,5-dihydro-3-(2,4,6-trimethylphenyl)-, chloride (9CI)
    • 1-[2,6-di(propan-2-yl)phenyl]-3-(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-3-ium;chloride
    • 1-(2,6-Diisopropylphenyl)-3-mesityl-4,5-dihydro-1H-imidazol-3-ium chloride
    • 1-(2,6-Diisopropylphenyl)-3-(2,4,6-trimethylphenyl)-imidazolinium chloride, 97%
    • CS-0085083
    • 3-(2,6-diisopropylphenyl)-1-(2,4,6-trimethylphenyl)-4,5-dihydro-1??-imidazol-1-ylium chloride
    • E76589
    • 866926-59-2
    • SCHEMBL820071
    • 1-(2,6-Diisopropropylphenyl)-3-(2,4,6-trimethylphenyl)-4,5-dihydroimidazolium chloride
    • 1-(2,6-Diisopropylphenyl)-3-mesityl-4,5-dihydro-1H-imidazol-3-iumchloride
    • DTXSID30469545
    • 1-(2,6-Di-i-propylphenyl)-3-(2,4,6-trimethylphenyl)-4,5-dihydroimidazolium chloride
    • MFCD17018754
    • 1-(2,6-Diisopropylphenyl)-3-(2,4,6-trimethylphenyl)-imidazolinium chloride
    • BS-51168
    • MDL： MFCD17018754
    • Inchi： 1S/C24H33N2.ClH/c1-16(2)21-9-8-10-22(17(3)4)24(21)26-12-11-25(15-26)23-19(6)13-18(5)14-20(23)7;/h8-10,13-17H,11-12H2,1-7H3;1H/q+1;/p-1
    • InChI Key： RHFFYNDQCMNENO-UHFFFAOYSA-M
    • SMILES： [Cl-].C1C=C(C(C)C)C([N+]2CCN(C3C(C)=CC(C)=CC=3C)C=2)=C(C(C)C)C=1

Computed Properties

  • Exact Mass: 384.23300
  • Monoisotopic Mass: 384.2332268g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 27
  • Rotatable Bond Count: 4
  • Complexity: 466
  • Covalently-Bonded Unit Count: 2
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 6.2?2

Experimental Properties

  • Melting Point: >300?°C
  • PSA: 6.25000
  • LogP: 3.07890
  • Sensitiveness: air sensitive

1H-Imidazolium,1-[2,6-bis(1-methylethyl)phenyl]-4,5-dihydro-3-(2,4,6-trimethylphenyl)-,chloride Security Information

  • Hazardous Material transportation number：NONH for all modes of transport
  • WGK Germany：3

1H-Imidazolium,1-[2,6-bis(1-methylethyl)phenyl]-4,5-dihydro-3-(2,4,6-trimethylphenyl)-,chloride Pricemore >>

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1H-Imidazolium,1-[2,6-bis(1-methylethyl)phenyl]-4,5-dihydro-3-(2,4,6-trimethylphenyl)-,chloride Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: Oxalyl chloride Solvents: Dimethylformamide ,  Dichloromethane ;  4 h, rt
1.2 Reagents: Triethylamine Solvents: Dichloromethane ;  0 °C; 0 °C → rt; 18 h, rt
2.1 Reagents: (T-4)-Trihydro(tetrahydrofuran)boron Solvents: Tetrahydrofuran ;  18 h, reflux
2.2 Reagents: Methanol ;  rt
2.3 Reagents: Hydrochloric acid Solvents: Triethyl orthoformate ,  Water ;  2 h, 120 °C
Reference
Room-Temperature Negishi Cross-Coupling of Unactivated Alkyl Bromides with Alkyl Organozinc Reagents Utilizing a Pd/N-Heterocyclic Carbene Catalyst
Hadei, Niloufar; et al, Journal of Organic Chemistry, 2005, 70(21), 8503-8507

Production Method 2

Reaction Conditions
1.1 Reagents: (T-4)-Trihydro(tetrahydrofuran)boron ;  18 h, 75 °C
1.2 Reagents: Hydrochloric acid Solvents: Cyclopentyl methyl ether
2.1 0.5 h, 100 °C
Reference
The Effect of Symmetric and Asymmetric NHCs on the Structure and Catalytic Properties of Dialkylgallium Alkoxides in the Ring-Opening Polymerization of rac-Lactide-Linking the Structure, Activity, and Stereoselectivity
Dabrowska, Anna Maria; et al, Organometallics, 2021, 40(9), 1221-1234

Production Method 3

Reaction Conditions
1.1 24 h, 185 °C
2.1 Reagents: (T-4)-Trihydro(tetrahydrofuran)boron Solvents: Tetrahydrofuran ;  rt → 65 °C; 15 h, 65 °C
3.1 Solvents: Triethyl orthoformate ;  rt → 125 °C; 12 h, 125 °C
Reference
Ruthenium Metallacycles Derived from 14-Electron Complexes. New Insights into Olefin Metathesis Intermediates
Wenzel, Anna G.; et al, Journal of the American Chemical Society, 2006, 128(50), 16048-16049

Production Method 4

Reaction Conditions
1.1 Solvents: Triethyl orthoformate ;  rt → 125 °C; 12 h, 125 °C
Reference
Ruthenium Metallacycles Derived from 14-Electron Complexes. New Insights into Olefin Metathesis Intermediates
Wenzel, Anna G.; et al, Journal of the American Chemical Society, 2006, 128(50), 16048-16049

Production Method 5

Reaction Conditions
1.1 0.5 h, 100 °C
Reference
The Effect of Symmetric and Asymmetric NHCs on the Structure and Catalytic Properties of Dialkylgallium Alkoxides in the Ring-Opening Polymerization of rac-Lactide-Linking the Structure, Activity, and Stereoselectivity
Dabrowska, Anna Maria; et al, Organometallics, 2021, 40(9), 1221-1234

Production Method 6

Reaction Conditions
1.1 Reagents: (T-4)-Trihydro(tetrahydrofuran)boron Solvents: Tetrahydrofuran ;  18 h, reflux
1.2 Reagents: Methanol ;  rt
1.3 Reagents: Hydrochloric acid Solvents: Triethyl orthoformate ,  Water ;  2 h, 120 °C
Reference
Room-Temperature Negishi Cross-Coupling of Unactivated Alkyl Bromides with Alkyl Organozinc Reagents Utilizing a Pd/N-Heterocyclic Carbene Catalyst
Hadei, Niloufar; et al, Journal of Organic Chemistry, 2005, 70(21), 8503-8507

Production Method 7

Reaction Conditions
1.1 Reagents: (T-4)-Trihydro(tetrahydrofuran)boron Solvents: Tetrahydrofuran ;  rt → 65 °C; 15 h, 65 °C
2.1 Solvents: Triethyl orthoformate ;  rt → 125 °C; 12 h, 125 °C
Reference
Ruthenium Metallacycles Derived from 14-Electron Complexes. New Insights into Olefin Metathesis Intermediates
Wenzel, Anna G.; et al, Journal of the American Chemical Society, 2006, 128(50), 16048-16049

Production Method 8

Reaction Conditions
1.1 Reagents: Triethylamine Solvents: Tetrahydrofuran ;  5 min, 0 °C; 5 min, 0 °C; 1.5 h, rt
2.1 24 h, 185 °C
3.1 Reagents: (T-4)-Trihydro(tetrahydrofuran)boron Solvents: Tetrahydrofuran ;  rt → 65 °C; 15 h, 65 °C
4.1 Solvents: Triethyl orthoformate ;  rt → 125 °C; 12 h, 125 °C
Reference
Ruthenium Metallacycles Derived from 14-Electron Complexes. New Insights into Olefin Metathesis Intermediates
Wenzel, Anna G.; et al, Journal of the American Chemical Society, 2006, 128(50), 16048-16049

1H-Imidazolium,1-[2,6-bis(1-methylethyl)phenyl]-4,5-dihydro-3-(2,4,6-trimethylphenyl)-,chloride Raw materials

1H-Imidazolium,1-[2,6-bis(1-methylethyl)phenyl]-4,5-dihydro-3-(2,4,6-trimethylphenyl)-,chloride Preparation Products

1H-Imidazolium,1-[2,6-bis(1-methylethyl)phenyl]-4,5-dihydro-3-(2,4,6-trimethylphenyl)-,chloride Related Literature

866926-59-2 (1H-Imidazolium,1-[2,6-bis(1-methylethyl)phenyl]-4,5-dihydro-3-(2,4,6-trimethylphenyl)-,chloride) Related Products

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