366188

N-Benzylcinchoninium chloride

98%

• Synonym(s): 9-Hydroxy-1-(phenylmethyl)cinchonanium chloride, BCNC
• Empirical Formula (Hill Notation): C₂₆H₂₉ClN₂O
• CAS Number: 69221-14-3
• Molecular Weight: 420.97
• Beilstein: 5232950
• EC Number: 273-915-8
• MDL number: MFCD00082423
• UNSPSC Code: 12352005
• PubChem Substance ID: 24862625
• NACRES: NA.22

Properties

• Assay: 98%
• form: solid
• optical activity: [α]20/D +169°, c = 0.4 in H₂O
• mp: 256 °C (dec.) (lit.)
• functional group: hydroxyl; phenyl
• SMILES string: [Cl-].O[C@H]([C@H]1C[C@@H]2CC[N+]1(C[C@@H]2C=C)Cc3ccccc3)c4ccnc5ccccc45
• InChI: 1S/C26H29N2O.ClH/c1-2-20-18-28(17-19-8-4-3-5-9-19)15-13-21(20)16-25(28)26(29)23-12-14-27-24-11-7-6-10-22(23)24;/h2-12,14,20-21,25-26,29H,1,13,15-18H2;1H/q+1;/p-1/t20-,21-,25+,26-,28?;/m0./s1
• InChI key: FCHYSBWCOKEPNQ-YGNISETGSA-M

Description

Application

Phase-transfer catalyst involved in:

• Enantioselective alkylation of malonic diester with alkyl halides
• Hydrolysis of enol esters
• Asymmetric 6π electrocyclization for synthesis of functionalized indolines
• Asymmetric Michael addition
• Alkylation of monosubstituted indolinones with alkylhalides
• Asymmetric destruction and kinetic resolution of 1-benzylated Reissert compounds

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves