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Sigma-Aldrich

N-Benzylcinchonidinium bromide

97%

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About This Item

Empirical Formula (Hill Notation):
C26H29BrN2O
CAS Number:
118089-84-2
Molecular Weight:
465.43
MDL number:
MFCD02093777
UNSPSC Code:
12352101
NACRES:
NA.22

Assay

97%

optical activity

[α]20/D −138°, c = 1 in chloroform

mp

190 °C (dec.) (lit.)

Related Categories

General description

N-Benzylcinchonidinium bromide is a chiral phase-transfer catalyst (PTC).

Application

N-Benzylcinchonidinium bromide (BCDBr) can be used:
  • To prepare various 4-(bromomethyl)benzenesulfonamides, which are employed as catalysts for asymmetric benzylation reactions.
  • As a phase transfer catalyst in the synthesis of organogelators via Michael addition reaction.
  • To catalyze the enantioselective alkylation of tert-butyl glycinate-benzophenone Schiff base furnishing the corresponding chiral α-amino acid.
  • To resolve symmetric biaryldiols via formation of inclusion complex with diols.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

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)

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Enantioselective reactions of tert-butyl glycinate-benzophenone Schiff base catalyzed by chiral phase-transfer catalyst in aqueous media without any organic solvent.
Mase N, et al.
Tetrahedron Letters, 46(18), 3213-3216 (2005)
Synthesis of cinchonidinium salts containing sulfonamide functionalities and their catalytic activity in asymmetric alkylation reactions
Itsuno S, et al.
Tetrahedron Letters, 55(44), 6117-6120 (2014)

Articles

Maruoka Catalysts

Asymmetric phase transfer catalysis using the Maruoka catalysts has proven to be an ideal method for the enantioselective preparation of natural and unnatural α-alkyl and α,α-dialkyl-α-amino acids from glycine derivati

Cinchona Alkaloids

Asymmetric phase-transfer catalysis (PTC) has been recognized as a “green” alternative to many homogeneous synthetic organic transformations, and has found widespread application. Synthetically modified cinchona alkaloids are typical chiral organocatalysts used in asymmetric PTC.

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