95088-20-3

Basic information

• Product Name: N-(4-Trifloromethybenzyl)cinchoninum bromide
• Synonyms: N-(4-TRIFLUOROMETHYLBENZYL)CINCHONINIUM BROMIDE;N-(4-Trifloromethylbenzyl)cinchoninum Bromide;N-(4-Trifloromethybenzyl)cinchoninum bromide;N-(4-Trifluoromethybenzyl)cinchoninum bromide
• CAS NO: 95088-20-3
• Molecular Formula: Br*C₂₇H₂₈F₃N₂O
• Molecular Weight: 533.42
• Product Categories: Phase Transfer Reaction;Asymmetric Synthesis;Chiral Catalysts, Ligands, and Reagents
• Mol File: 95088-20-3.mol
• Article Data: 3

Chemical Properties

• Melting Point: 245 °C (dec.)(lit.)
• Appearance: /
• BRN: 9108995
• CAS DataBase Reference: N-(4-Trifloromethybenzyl)cinchoninum bromide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(4-Trifloromethybenzyl)cinchoninum bromide(95088-20-3)
• EPA Substance Registry System: N-(4-Trifloromethybenzyl)cinchoninum bromide(95088-20-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-26-36
• WGK Germany: 3
• F: 3
• Hazardous Substances Data: 95088-20-3(Hazardous Substances Data)

Usage

Description

N-(4-Trifloromethybenzyl)cinchoninum bromide is a cinchona-based catalyst, which is a type of alkaloid derived from the bark of the cinchona tree. It is known for its ability to catalyze various chemical reactions, particularly in the synthesis of complex organic compounds.

Uses

Used in Pharmaceutical Industry:
N-(4-Trifloromethybenzyl)cinchoninum bromide is used as a catalyst in the synthesis of Viridicatumtoxins B antibiotic and its analogues. This application is significant because it aids in the production of important pharmaceutical compounds that can be used for treating various diseases and infections.

InChI:InChI=1/C27H28F3N2O.BrH/c1-2-19-17-32(16-18-7-9-21(10-8-18)27(28,29)30)14-12-20(19)15-25(32)26(33)23-11-13-31-24-6-4-3-5-22(23)24;/h2-11,13,19-20,25-26,33H,1,12,14-17H2;1H/q+1;/p-1/t19?,20-,25+,26-,32+;/m0./s1

Upstream product

• 118-10-5 cinchonine 
• 402-49-3 4-bromomethyltrifluoromethylbenzene 
• 118-10-5 Cinchonin 

Relevant articles and documents

Asymmetric Alkylation of Anthrones, Enantioselective Total Synthesis of (?)- and (+)-Viridicatumtoxins B and Analogues Thereof: Absolute Configuration and Potent Antibacterial Agents

A phase transfer catalyzed asymmetric alkylation of anthrones with cyclic allylic bromides using quinidine- or quinine-derived catalysts is described. Utilizing mild basic conditions and as low as 0.5 mol % catalyst loading, and achieving up to >99:1 dr selectivity, this asymmetric reaction was successfully applied to produce enantioselectively (?)- and (+)-viridicatumtoxins B, and thus allowed assignment of the absolute configuration of this naturally occurring antibiotic. While the developed asymmetric synthesis of C10 substituted anthrones is anticipated to find wider applications in organic synthesis, its immediate application to the construction of a variety of designed enantiopure analogues of viridicatumtoxin B led to the discovery of highly potent, yet simpler analogues of the molecule. These studies are expected to facilitate drug discovery and development efforts toward new antibacterial agents.

Enantioselective phase-transfer-catalyzed intramolecular Aza-Michael reaction: Effective route to pyrazino-indole compounds

(Chemical Equation Presented) Producing polycycles: A mild and direct stereocontrolled route to pharmacologically active pyrazino-indol-1-ones has been developed. The optimal phase-transfer conditions provide variously functionalized ring-closed compounds