1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydro-3H-1λ5,3-imidazol-1-ylium chloride

• ChemBase ID: 142800
• Molecular Formular: C21H27ClN2
• Molecular Mass: 342.90548
• Monoisotopic Mass: 342.18627655
• SMILES: Cc1cc(c(c(c1)C)N1CC[N+](=C1)c1c(cc(cc1C)C)C)C.[Cl-]
• Canonical SMILES: Cc1cc(C)c(c(c1)C)N1CC[N+](=C1)c1c(C)cc(cc1C)C.[Cl-]
• InChI: InChI=1S/C21H27N2.ClH/c1-14-9-16(3)20(17(4)10-14)22-7-8-23(13-22)21-18(5)11-15(2)12-19(21)6;/h9-13H,7-8H2,1-6H3;1H/q+1;/p-1
• InChIKey: COGMCBFILULEOS-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydro-3H-1λ^5,3-imidazol-1-ylium chloride
• IUPAC Traditional name: 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydro-1λ^5,3-imidazol-1-ylium chloride
• Synonyms: 4,5-Dihydro-1,3-dimesityl-1H-imidazolium chloride; N,N′-(2,4,6-Trimethylphenyl)dihydroimidazolium chloride; 1,3-Bis(2,4,6-trimethylphenyl)imidazolinium chloride; 1,3-Dimesitylimidazolidinium chloride; 4,5-Dihydro-1,3-bis(2,4,6-trimethylphenyl)-1H-imidazolium chloride; 1,3-二(2,4,6-三甲苯)咪唑氯盐; 1,3-双(2,4,6-三甲基苯基)氯化咪唑

Database IDs

• CAS Number: 173035-10-4
• MDL Number: MFCD09039279
• PubChem SID: 24884213; 162237026
• PubChem CID: 2734917

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 2.944707
• LogD (pH = 7.4): 2.944707
• Log P: 2.944707
• Molar Refractivity: 111.7865 cm^3
• Polarizability: 37.47347 Å^3
• Polar Surface Area: 6.25 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 280-286 °C

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter

Product Information

• Purity: 95%
• Empirical Formula (Hill Notation): C21H27ClN2

DETAILS

Sigma Aldrich - 656631

Packaging
1, 5 g in glass bottle
Application
N-Heterocyclic Carbene Ligands Precursor to an N-heterocyclic carbene catalysts used for:
• A regioselective cycloadditon of terminal acetylenes with azides leading to 1,4-disubstitutedtriazoles. Internal acetylenes can also be used with this catalyst.1
• Markovnikov-type hydration of terminal alkynes2
• Hydrosilylation of ketones and cycloaddition of azides and alkynes3
• Suzuki-Miyaura reactions4
• Luminescence experiments5