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374482

Sigma-Aldrich

N-Benzylquininium chloride

95%

Synonym(s):
QUIBEC
Empirical Formula (Hill Notation):
C27H31ClN2O2
CAS Number:
Molecular Weight:
451.00
Beilstein:
5702637
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

95%

optical activity

[α]20/D −235°, c = 1.5 in H2O

mp

200-205 °C (dec.) (lit.)

SMILES string

[Cl-].COc1ccc2nccc([C@@H](O)[C@@H]3C[C@@H]4CC[N@+]3(C[C@@H]4C=C)Cc5ccccc5)c2c1

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-GOGFHWEMSA-M

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General description

N-Benzylquininium chloride (or Quibec) belongs to the class of cinchona family of alkaloids. It is used as a catalyst in the presence of hydroxide bases in various phase transfer reactions, epoxidations, alkylations, and Michael reactions.

Application

N-Benzylquininium chloride can be used as a phase transfer catalyst:
  • In the sulfenylation of various β-keto sulfoxides.
  • To synthesize N-carbamoyl-protected β-nitroamines from α-amido sulfones by asymmetric aza-Henry reaction.

Packaging

5 g in glass bottle

Storage Class Code

13 - Non 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

Certificate of Analysis

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Certificate of Origin

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