N-BENZYLCINCHONINIUM CHLORIDE

N-BENZYLCINCHONINIUM CHLORIDE Basic information
Product Name:N-BENZYLCINCHONINIUM CHLORIDE
Synonyms:N-BENZYLCINCHONINIUM CHLORIDE;BCNC;(9S)-1-benzyl-9-hydroxycinchonanium chloride;chiralphase-transfercatalyst;N-BENZYLCINCHONINUM CHLORIDE);(9S)-9-Hydroxy-1-(phenylmethyl)cinchonanium chloride;(+)-1-Benzylcinchoninium chloride;(+)-N-Benzylcinchone chloride
CAS:69221-14-3
MF:C26H29ClN2O
MW:420.97
EINECS:273-915-8
Product Categories:Alkaloids;Ammonium Chlorides (Quaternary);Asymmetric Synthesis;Biochemistry;Chiral Phase-Transfer Catalysts;Quaternary Ammonium Compounds;chiral;Quinoline Alkaloids;Quinolinecarboxylic Acids, etc.;Quinolines;Synthetic Organic Chemistry
Mol File:69221-14-3.mol
N-BENZYLCINCHONINIUM CHLORIDE Structure
N-BENZYLCINCHONINIUM CHLORIDE Chemical Properties
Melting point 256 °C (dec.)(lit.)
refractive index 168.5 ° (C=0.4, MeOH:H2O=1:5)
storage temp. Inert atmosphere,Room Temperature
solubility slightly sol. in Methanol
form powder to crystaline
color White to Almost white
optical activity[α]20/D +169°, c = 0.4 in H2O
BRN 5232950
CAS DataBase Reference69221-14-3(CAS DataBase Reference)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36
WGK Germany 3
HS Code 29339900
MSDS Information
ProviderLanguage
SigmaAldrich English
N-BENZYLCINCHONINIUM CHLORIDE Usage And Synthesis
Chemical PropertiesSolid
UsesPhase-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
Purification MethodsRecrystallise the chloride from isoPrOH, toluene or small volumes of H2O. It is a good chiral phase transfer catalyst [Julia et al. J Chem Soc, Perkin Trans 1 574 1981, Hughes et al. J Am Chem Soc 106 446 1984, Hughes et al. J Org Chem 52 4745 1987].
N-BENZYLCINCHONINIUM CHLORIDE Preparation Products And Raw materials
2-(3-METHYLPIPERIDIN-1-YL)PROPAN-1-OL Cinchonine Benzyltriethylammonium chloride N-BUTYLTRIETHYLAMMONIUM CHLORIDE (1-BENZYL-2-PIPERIDINYL)METHANOL BENZYL(2-HYDROXYETHYL)DIMETHYLAMMONIUM CHLORIDE Benzyltripropylammonium chloride N-BENZYLCINCHONINIUM CHLORIDE 6-BENZYLAMINO-1-HEXANOL Methyltripropyl ammonium chloride Tetraethylammonium Chloride (R)(-)-2-BENZYLAMINO-1-BUTANOL N-Benzyl-N-methylpiperidinium chloride N-BENZYLQUINIDINIUM CHLORIDE QUINUCLIDINE HYDROCHLORIDE Mepiquat chloride QUINCORIDINE 2-HYDROXY-4-PYRIDYLETHYLAMINE

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