67174-25-8

Basic information

• Product Name: N-BENZYLQUININIUM CHLORIDE
• Synonyms: N-BENZYLQUININIUM CHLORIDE;QUIBEC;N-Benzylquininium Chloride [Chiral Phase-Transfer Catalyst];N-Benzylquininium chloride ,98%;CinchonaniuM, 9-hydroxy-6'-Methoxy-1-(phenylMethyl)-,chloride, (8a,9R)-;1-Benzylquininium chloride;N-Benzylquininium chloride 95%;(2S,4S,5R)
• CAS NO: 67174-25-8
• Molecular Formula: C₂₇H₃₁N₂O₂*Cl
• Molecular Weight: 451
• EINECS: 224-828-9
• Product Categories: Alkaloids;Alkoxyquinolines;Ammonium Chlorides (Quaternary);Asymmetric Synthesis;Biochemistry;Chiral Phase-Transfer Catalysts;Quaternary Ammonium Compounds;Quinoline Alkaloids;Quinolines;Synthetic Organic Chemistry
• Mol File: 67174-25-8.mol

Chemical Properties

• Melting Point: 200-205 °C (dec.)(lit.)
• Appearance: /
• Refractive Index: 227.5 ° (C=1.5, H2O)
• Storage Temp.: 2-8°C
• BRN: 5702637
• CAS DataBase Reference: N-BENZYLQUININIUM CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-BENZYLQUININIUM CHLORIDE(67174-25-8)
• EPA Substance Registry System: N-BENZYLQUININIUM CHLORIDE(67174-25-8)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 67174-25-8(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
N-Benzylquininium chloride is used as a phase transfer catalyst for the sulfenylation of various β-keto sulfoxides and the synthesis of N-carbamoyl-protected β-nitroamines from α-amido sulfones by asymmetric aza-Henry reaction. Its application in these processes facilitates the formation of desired products with improved efficiency and selectivity.
Used in Pharmaceutical Industry:
As a catalyst in the synthesis of various pharmaceutical compounds, N-Benzylquininium chloride plays a crucial role in the development of new drugs and the improvement of existing ones. Its ability to catalyze a wide range of reactions makes it a valuable tool in the synthesis of complex organic molecules with potential therapeutic applications.
Used in Organic Chemistry Research:
N-Benzylquininium chloride is utilized in academic and industrial research settings to explore new reaction pathways and develop innovative synthetic methods. Its unique catalytic properties enable chemists to study and understand the underlying mechanisms of various organic transformations, leading to advancements in the field of organic chemistry.

InChI:InChI=1/C27H31N2O2.ClH/c1-3-20-18-29(17-19-7-5-4-6-8-19)14-12-21(20)15-26(29)27(30)23-11-13-28-25-10-9-22(31-2)16-24(23)25;/h3-11,13,16,20-21,26-27,30H,1,12,14-15,17-18H2,2H3;1H/q+1;/p-1/t20-,21-,26+,27-,29?;/m0./s1

Upstream product

• 100-44-7 benzyl chloride 
• 130-95-0 Quinine 

Downstream Products

• 77452-62-1 (-)-O-acetyl-N-benzylquinium chloride 
• 116140-63-7 N-Benzylquininium methoxide 

Relevant articles and documents

Bioactive indanes: Proof of concept study for enantioselective synthetic routes to ph46a, a new potential anti-inflammatory agent

PH46A is a single enantiomer and a member of the 1,2-indane dimer family. It has two contiguous stereogenic centers with S,S configurations, one of which being a quaternary center, which has been developed as a clinical candidate for the treatment of inflammatory and autoimmune conditions. The current synthetic route to PH46A involves the generation of an unwanted enantiomer (R,R)-7, thus reducing the final yield significantly. Therefore, we have investigated potential alternatives to improve the efficiency of this synthesis. The first phase of the study has demonstrated proof of principle for a chiral alkylation of ketone 3 using phase-transfer catalysis, providing a key intermediate ketone (S)-4. The parent alkaloids required for the synthesis of PH46A, quinine or cinchonidine, have also been identified. Promising enantiomeric excesses of up to 50% have been achieved to date, and the use of an alternative substrate, unsaturated ketone 9, has also opened up further avenues for optimisation in future studies. The second part of the study involved preliminary screening the effects of a panel of hydrolase enzymes on (rac)-4 in order to identify a potential chemo-enzymatic route to optimise the introduction of chirality into PH46A at early stage of the synthesis. The hydrolase module has also yielded positive results; enzyme AH-46 with MtBE providing a selectivity factor of 8.4 with enantiomeric excess of 77%. Overall, positive results were obtained in this proof of concept study described herein. It is believed that conditions of both chiral PTC alkylation and biocatalytic hydrolysis could be optimised to further enhance the selectivity and improve the overall yield. This work is currently ongoing.

Asymmetric dearomative spirolactonization of naphthols using λ3-iodanes under chiral phase-transfer catalysis

The asymmetric phase-transfer catalytic effect of chiral Cinchona alkaloid-derived quaternary ammonium salts was investigated in the context of the λ3-iodane-mediated dearomative spirolactonization of naphthols. The scope and limitations of this methodology were evaluated using various substrates, which were converted into spirolactones in good yields and with enantiomeric excesses up to 58%.