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N-BENZYLCINCHONINIUM CHLORIDE

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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
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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 Reference
69221-14-3(CAS DataBase Reference)
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Safety Information

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-36
WGK Germany 
3
HS Code 
29339900

MSDS

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N-BENZYLCINCHONINIUM CHLORIDE Usage And Synthesis

Chemical Properties

Solid

Uses

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

Purification Methods

Recrystallise 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 CHLORIDESupplier

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