69221-14-3

Basic information

• Product Name: N-BENZYLCINCHONINIUM CHLORIDE
• Synonyms: N-BENZYLCINCHONINIUM CHLORIDE;BCNC;(9S)-1-benzyl-9-hydroxycinchonanium chloride;chiralphase-transfercatalyst;N-BENZYLCINCHONINUM CHLORIDE);N-Benzylcinchoninium Chloride [Chiral Phase-Transfer Catalyst];(+)-1-Benzylcinchoninium chloride;(+)-N-Benzylcinchone chloride
• CAS NO: 69221-14-3
• Molecular Formula: C₂₆H₂₉N₂O*Cl
• Molecular Weight: 420.97
• EINECS: 273-915-8
• Product Categories: chiral;Alkaloids;Ammonium Chlorides (Quaternary);Asymmetric Synthesis;Biochemistry;Chiral Phase-Transfer Catalysts;Quaternary Ammonium Compounds;Quinoline Alkaloids;Quinolinecarboxylic Acids, etc.;Quinolines;Synthetic Organic Chemistry
• Mol File: 69221-14-3.mol
• Article Data: 4

Chemical Properties

• Melting Point: 256 °C (dec.)(lit.)
• Appearance: /
• Refractive Index: 168.5 ° (C=0.4, MeOH:H2O=1:5)
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: slightly sol. in Methanol
• BRN: 5232950
• CAS DataBase Reference: N-BENZYLCINCHONINIUM CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-BENZYLCINCHONINIUM CHLORIDE(69221-14-3)
• EPA Substance Registry System: N-BENZYLCINCHONINIUM CHLORIDE(69221-14-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 69221-14-3(Hazardous Substances Data)

Usage

Chemical Properties

Solid

Uses

Phase-transfer catalyst involved in:Enantioselective alkylation of malonic diester with alkyl halidesHydrolysis of enol estersAsymmetric 6π electrocyclization for synthesis of functionalized indolinesAsymmetric Michael additionAlkylation of monosubstituted indolinones with alkylhalidesAsymmetric destruction and kinetic resolution of 1-benzylated Reissert compounds

Purification Methods

Recrystallise the chloride from isoPrOH, toluene or small volumes of H2O. It is a good chiral phase transfer catalyst [Julia et al. J Chem Soc, Perkin Trans 1 574 1981, Hughes et al. J Am Chem Soc 106 446 1984, Hughes et al. J Org Chem 52 4745 1987].

InChI:InChI=1/C26H29N2O.ClH/c1-2-20-18-28(17-19-8-4-3-5-9-19)15-13-21(20)16-25(28)26(29)23-12-14-27-24-11-7-6-10-22(23)24;/h2-12,14,20-21,25-26,29H,1,13,15-18H2;1H/q+1;/p-1/t20-,21+,25-,26+,28-;/m1./s1

Upstream product

• 100-44-7 benzyl chloride 
• 118-10-5 Cinchonin 
• 485-71-2 Cinchonidin 

Downstream Products

• 116140-61-5 N-Benzylcinchoninium methoxide 
• 116140-82-0 Ethanolate(1S,2R,4S,5R)-1-benzyl-2-((S)-hydroxy-quinolin-4-yl-methyl)-5-vinyl-1-azonia-bicyclo[2.2.2]octane; 
• 18531-99-2 (S)-[1,1']-binaphthalenyl-2,2'-diol 
• 1092983-06-6 N-9-benzylcinchonidinium p-vinylbenzoate 

Relevant articles and documents

Preparation method of optically pure 1, 1'-spirobiindane-6, 6'-diol derivative

The invention discloses a preparation method of an optically pure 1, 1'-spirobiindane-6, 6'-diol derivative. The derivative is shown in the formula I. The optically pure 1, 1'-spirobiindane-6, 6'-diolderivative is prepared from optically pure N-benzylcinchonidinium chloride as an inclusion main body and a racemic 1, 1'-spirobiindane-6, 6'-diol derivative as a guest through an inclusion and resolution method. The novel method can acquire the 1, 1'-spirobiindane-6, 6'-diol derivative with high optical purity and chemical purity and acquire two structures in a high yield, has simple separation and purification processes, realizes recovery and recycling of a lot of a resolving agent, is simple and efficient, realizes a low cost and is suitable for industrial promotion. The optically pure 1, 1'-spirobiindane-6, 6'-diol derivative is a key raw material for the preparation of chiral spiro ligands or catalysts.

Perfectly green organocatalysis: Quaternary ammonium base triggered cyanosilylation of aldehydes

Quaternary ammonium bases, such as aqueous (CH3)4NOH, were found to be an extraordinarily efficient catalyst for cyanosilylation of aldehydes. The addition reaction of trimethylsilyl cyanide (TMSCN) to equivalent aldehydes could proceed smoothly with turnover frequency (TOF) up to 3000000 h-1 and in near 100% yield under solvent-free conditions. These organic catalysts also tolerated various aldehydes including aromatic, aliphatic and α,β-unsaturated aldehydes. This process perfectly conforms to the features of green chemistry: no waste regarding side-products and unconverted reactants, solvent-free, excellent catalytic activity, and no requirement for separation.