Skip to Content
Merck
CN

524433

Sigma-Aldrich

N-Benzylcinchonidinium bromide

97%

Sign Into View Organizational & Contract Pricing

Select a Size


About This Item

Empirical Formula (Hill Notation):
C26H29BrN2O
CAS Number:
Molecular Weight:
465.43
MDL number:
UNSPSC Code:
12352101
NACRES:
NA.22
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

Quality Level

Assay

97%

optical activity

[α]20/D −138°, c = 1 in chloroform

mp

190 °C (dec.) (lit.)

InChI key

UUVFTQCFSNVLGV-SPTWEYDNSA-M

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

Signal Word

Warning

Hazard Statements

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

Regulatory Information

新产品
This item has

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
Separation of the Enantiomers of 2, 2?-Dihydroxy-1, 1?-binaphthyl and 10, 10?-Dihydroxy-9, 9?-biphenanthryl by Complexation with N-Alkylcinchonidinium Halides
Tanaka K, et al.
Angewandte Chemie (International ed. in English), 32(8), 1147-1148 (1993)
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 green organogelators with a sulfide linkage via solvent-free Michael addition: soft templates for the preparation of size-controlled gold nanoparticles
Delbecq F, et al.
Tetrahedron Letters, 54(7), 651-656 (2013)

Articles

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.

Maruoka catalysts enable enantioselective preparation of α-amino acids from glycine derivatives via asymmetric phase transfer catalysis.

不对称相转移催化(PTC)已被公认为是许多均相合成有机转化的“绿色”替代方法,并且已被广泛应用。合成修饰的金鸡纳生物碱是用于不对称PTC的典型手性有机催化剂。

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service