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About This Item
Empirical Formula (Hill Notation):
C26H29BrN2O
CAS Number:
Molecular Weight:
465.43
MDL number:
UNSPSC Code:
12352101
NACRES:
NA.22
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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.
Signal Word
Warning
Hazard Statements
Precautionary 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
Certificates of Analysis (COA)
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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)
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)
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)
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)
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