1-[(3R,5S,7s)-adamantan-1-yl]-3-(2,4,6-trimethylphenyl)-4,5-dihydro-3H-1λ5,3-imidazol-1-ylium chloride

• ChemBase ID: 141205
• Molecular Formular: C22H31ClN2
• Molecular Mass: 358.94794
• Monoisotopic Mass: 358.21757668
• SMILES: Cc1cc(c(c(c1)C)N1C=[N+](CC1)[C@@]12C[C@H]3C[C@@H](C1)C[C@H](C2)C3)C.[Cl-]
• Canonical SMILES: Cc1cc(C)cc(c1N1CC[N+](=C1)[C@]12C[C@@H]3C[C@@H](C2)C[C@@H](C1)C3)C.[Cl-]
• InChI: InChI=1S/C22H31N2.ClH/c1-15-6-16(2)21(17(3)7-15)23-4-5-24(14-23)22-11-18-8-19(12-22)10-20(9-18)13-22;/h6-7,14,18-20H,4-5,8-13H2,1-3H3;1H/q+1;/p-1/t18-,19+,20-,22-
• InChIKey: MJOMRTQWLPXDJQ-ZFCGJYDVSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(3R,5S,7s)-adamantan-1-yl]-3-(2,4,6-trimethylphenyl)-4,5-dihydro-3H-1λ^5,3-imidazol-1-ylium chloride
• IUPAC Traditional name: 1-[(3R,5S,7s)-adamantan-1-yl]-3-(2,4,6-trimethylphenyl)-4,5-dihydro-1λ^5,3-imidazol-1-ylium chloride
• Synonyms: 1-(1-Adamantyl)-3-(2,4,6-trimethylphenyl)-4,5-dihydroimidazolium chloride; 1-(1-Adamantyl)-3-(2,4,6-trimethylphenyl)imidazolinium chloride; 1-(1-金刚烷基)-3-(2,4,6-三甲基苯基)-4,5-二氢咪唑鎓氯化物; 1-(1-金刚烷基)-3-(2,4,6-三甲基苯基)氯化咪唑啉

Database IDs

• CAS Number: 639820-61-4
• MDL Number: MFCD08276859
• PubChem SID: 162235440; 24884707
• PubChem CID: 16218157

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 1.5132072
• LogD (pH = 7.4): 1.5132072
• Log P: 1.5132072
• Molar Refractivity: 112.5021 cm^3
• Polarizability: 38.827065 Å^3
• Polar Surface Area: 6.25 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 263-280 °C

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Empirical Formula (Hill Notation): C22H31ClN2

DETAILS

Sigma Aldrich - 665029

Packaging
100, 500 mg in glass bottle
Legal Information
Sold under license from Kanata Chemical Technologies Inc. for research purposes only.
Application
Reactant for:
• Preparation of chelated ruthenium alkoxybenzylidene imidazolidene carbene pivalate catalysts for Z-selective olefin metathesis1
• Use in ring-opening metathesis polymerization and ring-closing metathesis reactions via Grubbs catalyst mediated reactions2
• Preparation of adamantyl-substituted N-heterocyclic carbene ligands in second-generation Grubbs-type iridium metathesis catalysis3