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Sigma-Aldrich

N-Benzylquininium chloride

95%

Synonym(s):

QUIBEC

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About This Item

Empirical Formula (Hill Notation):
C27H31ClN2O2
CAS Number:
67174-25-8
Molecular Weight:
451.00
Beilstein:
5702637
MDL number:
MFCD00198105
UNSPSC Code:
12352005
PubChem Substance ID:
24863311
NACRES:
NA.22

Quality Level

100

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.

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Phase-Transfer-Catalyzed Asymmetric Aza-Henry Reaction Using N-Carbamoyl Imines Generated In Situ from ?-Amido Sulfones
Fini F, et al.
Angewandte Chemie (International ed. in English), 44(48), 7975-7978 (2005)
N-Benzylquininium Chloride
Bos Mary E, et al.
Encyclopedia of Reagents for Organic Synthesis, Second Edition, 1-7 (2001)
Sulfenylation of β-keto sulfoxides. III. Diastereoselectivity induced by a chiral phase transfer catalyst
Wladislaw B, et al.
Tetrahedron, 55(41), 12023-12030 (1999)

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