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374482

Sigma-Aldrich

N-Benzylquininium chloride

95%

Synonym(s):

QUIBEC

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About This Item

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

Pricing and availability is not currently available.

Quality Level

Assay

95%

optical activity

[α]20/D −235°, c = 1.5 in H2O

mp

200-205 °C (dec.) (lit.)

functional group

hydroxyl
phenyl

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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1 of 4

This Item
SRP3187GF170SRP3296
assay

>98% (SDS-PAGE and HPLC)

assay

≥98% (HPLC), ≥98% (SDS-PAGE)

assay

>97% (SDS-PAGE and HPLC)

assay

≥80% (HPLC), ≥80% (SDS-PAGE)

impurities

<0.1 μg/mg protein endotoxin (<1EU/μg)

impurities

<0.1 EU/μg endotoxin, tested

impurities

<0.1 μg/mg protein endotoxin (<1EU/μg)

impurities

<0.1 EU/μg endotoxin, tested

shipped in

dry ice

shipped in

wet ice

shipped in

dry ice

shipped in

wet ice

UniProt accession no.

P04628

UniProt accession no.

O95388

UniProt accession no.

O94907

UniProt accession no.

O00755

Quality Level

100

Quality Level

-

Quality Level

100

Quality Level

-

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.[1]

Application

N-Benzylquininium chloride can be used as a phase transfer catalyst:
  • In the sulfenylation of various β-keto sulfoxides.[2]
  • To synthesize N-carbamoyl-protected β-nitroamines from α-amido sulfones by asymmetric aza-Henry reaction.[3]

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

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    Sulfenylation of β-keto sulfoxides. III. Diastereoselectivity induced by a chiral phase transfer catalyst
    Wladislaw B, et al.
    Tetrahedron, 55(41), 12023-12030 (1999)
    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)

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