3-[(2S)-1-hydroxy-4-methylpentan-2-yl]-1-(2,4,6-trimethylphenyl)-4,5-dihydro-1H-imidazol-3-ium; hexafluoro-λ5-phosphanuide

• ChemBase ID: 142699
• Molecular Formular: C18H29F6N2OP
• Molecular Mass: 434.3998402
• Monoisotopic Mass: 434.19216951
• SMILES: Cc1cc(c(c(c1)C)N1CC[N+](=C1)[C@@H](CC(C)C)CO)C.F[P-](F)(F)(F)(F)F
• Canonical SMILES: F[P-](F)(F)(F)(F)F.OC[C@@H]([N+]1=CN(CC1)c1c(C)cc(cc1C)C)CC(C)C
• InChI: InChI=1S/C18H29N2O.F6P/c1-13(2)8-17(11-21)19-6-7-20(12-19)18-15(4)9-14(3)10-16(18)5;1-7(2,3,4,5)6/h9-10,12-13,17,21H,6-8,11H2,1-5H3;/q+1;-1/t17-;/m0./s1
• InChIKey: NTQWYGMQOMHOQG-LMOVPXPDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(2S)-1-hydroxy-4-methylpentan-2-yl]-1-(2,4,6-trimethylphenyl)-4,5-dihydro-1H-imidazol-3-ium; hexafluoro-λ^5-phosphanuide
• IUPAC Traditional name: 1-[(2S)-1-hydroxy-4-methylpentan-2-yl]-3-(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-1-ium hexafluorophosphate
• Synonyms: 1-(S)-Leucinol-3-(2,4,6-trimethylphenyl)-3H-imidazolium hexafluorophosphate; SIMes-leucinol; 1-(S)-亮氨醇-3-(2,4,6-三甲苯基)-3H-六氟磷酸咪唑鎓; SIMes-亮氨醇

Database IDs

• PubChem SID: 162236925
• PubChem CID: 11476023

CALCULATED PROPERTIES

• Acid pKa: 14.234727
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 0.40238395
• LogD (pH = 7.4): 0.40238515
• Log P: 0.40238395
• Molar Refractivity: 101.27 cm^3
• Polarizability: 34.246807 Å^3
• Polar Surface Area: 26.48 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 168-170 °C

Safety Information

• European Hazard Symbols: Corrosive (C)
• UN Number: 3261
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2
• Risk Statements: 34
• Safety Statements: 26-36/37/39-45
• GHS Pictograms: GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H314
• GHS Precautionary statements: P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 3261 8/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: 97%
• Empirical Formula (Hill Notation): C18H27F6N2OP

DETAILS

Sigma Aldrich - 700029

Application
Chiral NHC used with copper for conjugate addition of Grignards to enones1
Packaging
1 g in glass bottle
250 mg in glass bottle