(2R,4S,5R)-5-ethenyl-2-[(S)-hydroxy(quinolin-4-yl)methyl]-1-{[4-(trifluoromethyl)phenyl]methyl}-1-azabicyclo[2.2.2]octan-1-ium bromide

• ChemBase ID: 151177
• Molecular Formular: C27H28BrF3N2O
• Molecular Mass: 533.4232296
• Monoisotopic Mass: 532.13371019
• SMILES: C=C[C@H]1C[N+]2(CC[C@H]1C[C@@H]2[C@H](c1ccnc2c1cccc2)O)Cc1ccc(cc1)C(F)(F)F.[Br-]
• Canonical SMILES: C=C[C@H]1C[N+]2(CC[C@H]1C[C@@H]2[C@H](c1ccnc2c1cccc2)O)Cc1ccc(cc1)C(F)(F)F.[Br-]
• InChI: InChI=1S/C27H28F3N2O.BrH/c1-2-19-17-32(16-18-7-9-21(10-8-18)27(28,29)30)14-12-20(19)15-25(32)26(33)23-11-13-31-24-6-4-3-5-22(23)24;/h2-11,13,19-20,25-26,33H,1,12,14-17H2;1H/q+1;/p-1/t19-,20-,25+,26-,32?;/m0./s1
• InChIKey: LOCWWLLFHKDFLF-KFGLDPKJSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,4S,5R)-5-ethenyl-2-[(S)-hydroxy(quinolin-4-yl)methyl]-1-{[4-(trifluoromethyl)phenyl]methyl}-1-azabicyclo[2.2.2]octan-1-ium bromide
• IUPAC Traditional name: (2R,4S,5R)-5-ethenyl-2-[(S)-hydroxy(quinolin-4-yl)methyl]-1-{[4-(trifluoromethyl)phenyl]methyl}-1-azabicyclo[2.2.2]octan-1-ium bromide
• Synonyms: N-[4-(Trifluoromethyl)benzyl]cinchoninium bromide; N-(4-三氟甲基苄基)辛可宁溴化物

Database IDs

• CAS Number: 95088-20-3
• MDL Number: MFCD00082433
• Beilstein Number: 9108995
• PubChem SID: 24889566; 24862623; 162245334
• PubChem CID: 11421253

CALCULATED PROPERTIES

• Acid pKa: 12.609214
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 1.0831772
• LogD (pH = 7.4): 1.1108068
• Log P: 1.1111202
• Molar Refractivity: 134.7303 cm^3
• Polarizability: 48.05101 Å^3
• Polar Surface Area: 33.12 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 245 °C (dec.)(lit.)
• Optical Rotation: [α]20/D +140±20° in ethanol

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 22-24/25-26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥98.0% (AT); 80%
• Grade: purum
• Compostion: N-(4-trifluoromethylbenzyl)cinchoninium bromide, ~85%; N-(4-trifluoromethylbenzyl)dihydrocinchoninium bromid, ~15%
• Empirical Formula (Hill Notation): C27H28BrF3N2O

DETAILS

Sigma Aldrich - 366161

Other Notes
Remainder N-[4-(trifluoromethyl)benzyl]dihydrochoninium bromide
Packaging
1, 5 g in glass bottle

Sigma Aldrich - 91851

Other Notes
PT-catalyst for the first efficient catalytic asymmetric alkylation1,2,3; Catalyst for asymetric hydroxylation4