N-Benzylquininium chloride - CAS 67174-25-8

N-Benzylquininium chloride is a cinchona alkaloids organocatalyst that has been intensively applied as either standalone catalysts or chiral ligands in catalytic asymmetric reactions.

Catalog Number

67174-25-8

CAS

67174-25-8

IUPAC Name

(R)-[(2S,4S,5R)-1-benzyl-5-ethenyl-1-azoniabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol;chloride

Synonyms

QUIBEC

Molecular Weight

451.00

Molecular Formula

C27H31ClN2O2

Product Information

Canonical SMILES

C=C[C@@H]1[C@](CC2)([H])C[C@@H]([C@H](O)C3=CC=NC4=CC=C(OC)C=C34)[N+]2(CC5=CC=CC=C5)C1.[Cl-]

InChI

InChI=1S/C27H31N2O2.ClH/c1-3-20-18-29(17-19-7-5-4-6-8-19)14-12-21(20)15-26(29)27(30)23-11-13-28-25-10-9-22(31-2)16-24(23)25;/h3-11,13,16,20-21,26-27,30H,1,12,14-15,17-18H2,2H3;1H/q+1;/p-1/t20-,21-,26-,27+,29?;/m0./s1

InChI Key

JYDIJFKNXHPWBJ-UNGVVQABSA-M

Purity

≥98%

MDL

MFCD00198105

Physical State

Solid

Appearance

Powder or Crystals

Storage

Sealed in dry. Keep cold.

Melting Point

200-205 °C

Optical Activity

-235°(c=1.5 in water)

TSCA

WGK Germany

Safety Information

Signal Word

Warning

Precautionary Statement

P305 - P351 - P338

Hazard Statements

H315 - H319

Reference Reading

1. Preparation of benzyl quinine-modified monolithic column for reversed-phase capillary electrochromatography.

Lu Liu, Fang Xiao, Xintao Cheng, Xiaofeng Cheng, Zhenfu Lv, Wenshan Ni, Xiangju Mao. Anal Sci. 2021 Feb 10; 37(2): 261-266. DOI: 10.2116/analsci.20P075. PMID: 32418933.

N-Benzylquininium chloride is a versatile functional monomer with quinoline and benzyl groups, which is beneficial for reversed-phase chromatography. In this study, a novel monolithic column with reversed-phase mode was synthesized using N-benzylquininium chloride as the monomer and 3-(acryloyloxy)-2-hydroxypropyl methacrylate as the cross-linker in a binary porogenic solvent consisting of PEG 400 and a 0.05 M sodium hydroxide aqueous solution. The alkaline solution were found to be useful for the improvement of the mechanical stability of the porous monoliths. The monolithic column showed excellent reversed-phase selectivity and various compounds, such as alkylbenzenes, phenols and polycyclic aromatic hydrocarbons, were separated successfully. The highest column efficiency was 1.75 × 105N m-1. The relative standard deviations of the migration time for thiourea and four alkylbenzenes were all less than 5.0%, which indicates the monolithic column has good stability. The application of the monolithic column for the analysis of polycyclic aromatic hydrocarbons in spiked lake water samples illustrated its great potential for practical application.

The molarity calculator equation

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Mass