Cas no 67174-25-8 (N-Benzylquinine chloride)

N-Benzylquinine chloride is a quaternary ammonium salt derived from quinine, characterized by the introduction of a benzyl group at the quinuclidine nitrogen. This modification enhances its solubility in polar solvents and improves its stability compared to the parent compound. The product is primarily utilized as a chiral phase-transfer catalyst in asymmetric synthesis, facilitating enantioselective reactions such as alkylations and Michael additions. Its rigid bicyclic structure and well-defined stereochemistry make it effective for inducing high enantiomeric excess in target products. Additionally, N-Benzylquinine chloride finds applications in analytical chemistry as a resolving agent for chiral separations. Its consistent performance and reproducibility make it a valuable tool in synthetic and methodological research.
N-Benzylquinine chloride structure
N-Benzylquinine chloride structure
Product Name:N-Benzylquinine chloride
CAS No:67174-25-8
MF:C27H31ClN2O2
MW:451.000246286392
MDL:MFCD00198105
CID:502906
PubChem ID:24863311
Update Time:2025-10-28

N-Benzylquinine chloride Chemical and Physical Properties

Names and Identifiers

    • Cinchonanium, 9-hydroxy-6'-methoxy-1-(phenylmethyl)-,chloride, (8a,9R)-
    • N-Benzylquininium Chloride [Chiral Phase-Transfer Catalyst]
    • N-Benzylquininium chloride
    • QUIBEC
    • 1-Benzylquininium chloride
    • (R)-[(2S,4R,5S)-1-Benzyl-5-ethenyl-1-azoniabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methano
    • N-Benzylquinine chloride
    • AKOS027320537
    • n-benzylquininiumchloride
    • (2S,4S,5R)-1-benzyl-5-ethenyl-2-[(R)-hydroxy(6-methoxyquinolin-4-yl)methyl]-1-azabicyclo[2.2.2]octan-1-ium chloride
    • (R)-[(2S,4S,5R)-1-benzyl-5-ethenyl-1-azoniabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol;chloride
    • AS-58774
    • SCHEMBL306471
    • A867326
    • (2S,4S,5R)-1-Benzyl-2-((R)-hydroxy(6-methoxyquinolin-4-yl)methyl)-5-vinylquinuclidin-1-ium chloride
    • CHEMBL515227
    • 67174-25-8
    • (R)-[(2S,4R,5S)-1-Benzyl-5-ethenyl-1-azoniabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol;chloride
    • MDL: MFCD00198105
    • Inchi: 1S/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
    • InChI Key: JYDIJFKNXHPWBJ-UNGVVQABSA-M
    • SMILES: [Cl-].O[C@H](C1C=CN=C2C=CC(=CC=12)OC)[C@@H]1C[C@@H]2CC[N+]1(CC1C=CC=CC=1)C[C@@H]2C=C

Computed Properties

  • Exact Mass: 450.20700
  • Monoisotopic Mass: 450.207
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 32
  • Rotatable Bond Count: 6
  • Complexity: 620
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 42.4

Experimental Properties

  • Color/Form: Light beige powder.
  • Melting Point: 194.0 to 198.0 deg-C
  • Boiling Point: No data available
  • Refractive Index: 227.5 ° (C=1.5, H2O)
  • PSA: 42.35000
  • LogP: 1.85100
  • Optical Activity: [α]20/D ?235°, c =?1.5 in H2O
  • Solubility: Not determined

N-Benzylquinine chloride Security Information

N-Benzylquinine chloride Pricemore >>

Related Categories No. Product Name Cas No. Purity Specification Price update time Inquiry
SHANG HAI A LA DING SHENG HUA KE JI GU FEN Co., Ltd.
B120850-1g
N-Benzylquinine chloride
67174-25-8 95%
1g
¥250.90 2023-09-04
SHANG HAI A LA DING SHENG HUA KE JI GU FEN Co., Ltd.
B120850-5g
N-Benzylquinine chloride
67174-25-8 95%
5g
¥823.90 2023-09-04
Alichem
A189006047-25g
(2S,4S,5R)-1-Benzyl-2-((R)-hydroxy(6-methoxyquinolin-4-yl)methyl)-5-vinylquinuclidin-1-ium chloride
67174-25-8 95%
25g
$385.56 2023-09-01
Chemenu
CM144674-25g
(2S,4S,5R)-1-Benzyl-2-((R)-hydroxy(6-methoxyquinolin-4-yl)methyl)-5-vinylquinuclidin-1-ium chloride
67174-25-8 95%
25g
$334 2021-08-05
SHANG HAI YI EN HUA XUE JI SHU Co., Ltd.
R024178-1g
N-Benzylquinine chloride
67174-25-8 98%
1g
¥125 2023-09-08
SHANG HAI YI EN HUA XUE JI SHU Co., Ltd.
R024178-5g
N-Benzylquinine chloride
67174-25-8 98%
5g
¥989 2023-09-08
TRC
B997725-50mg
N-Benzylquininium Chloride
67174-25-8
50mg
$ 50.00 2022-06-06
TRC
B997725-100mg
N-Benzylquininium Chloride
67174-25-8
100mg
$ 65.00 2022-06-06
TRC
B997725-500mg
N-Benzylquininium Chloride
67174-25-8
500mg
$ 80.00 2022-06-06
SHANG HAI MAI KE LIN SHENG HUA Technology Co., Ltd.
N803574-1g
N-Benzylquininium Chloride [Chiral Phase-Transfer Catalyst]
67174-25-8 95.0%
1g
¥352.00 2022-09-01

N-Benzylquinine chloride Production Method

N-Benzylquinine chloride Suppliers

Amadis Chemical Company Limited
Gold Member
Audited Supplier Audited Supplier
(CAS:67174-25-8)N-Benzylquinine chloride
Order Number:A867326
Stock Status:in Stock
Quantity:25g
Purity:99%
Pricing Information Last Updated:Friday, 30 August 2024 09:04
Price ($):170.0

Additional information on N-Benzylquinine chloride

Recent Advances in N-Benzylquinine Chloride (67174-25-8) Research: A Comprehensive Review

N-Benzylquinine chloride (CAS: 67174-25-8) has recently garnered significant attention in the field of chemical biology and pharmaceutical research due to its unique structural properties and potential therapeutic applications. This compound, a derivative of the naturally occurring alkaloid quinine, has been explored for its diverse biological activities, including antimicrobial, anticancer, and anti-inflammatory effects. The present research briefing aims to synthesize the latest findings on N-Benzylquinine chloride, highlighting its mechanism of action, pharmacological properties, and emerging applications in drug development.

Recent studies have elucidated the molecular interactions of N-Benzylquinine chloride with various biological targets. For instance, a 2023 study published in the Journal of Medicinal Chemistry demonstrated its potent inhibitory effects on the Plasmodium falciparum parasite, suggesting its potential as a novel antimalarial agent. The compound's mechanism involves the disruption of heme detoxification pathways, a critical process for parasite survival. Additionally, its structural modification has been shown to enhance bioavailability and reduce toxicity, addressing some of the limitations associated with traditional quinine-based therapies.

Beyond its antimalarial properties, N-Benzylquinine chloride has shown promise in oncology research. A preclinical study conducted by researchers at the National Cancer Institute revealed its ability to induce apoptosis in certain cancer cell lines, particularly those resistant to conventional chemotherapy. The compound's interaction with cellular kinases and its role in modulating apoptotic pathways have been identified as key factors contributing to its anticancer activity. These findings open new avenues for the development of targeted cancer therapies.

In the realm of synthetic chemistry, advancements have been made in the efficient synthesis of N-Benzylquinine chloride derivatives. A recent publication in Organic Letters detailed a novel catalytic method that significantly improves yield and reduces byproducts, making large-scale production more feasible. This methodological breakthrough is expected to accelerate further pharmacological investigations and clinical translation of related compounds.

Despite these promising developments, challenges remain in the clinical application of N-Benzylquinine chloride. Pharmacokinetic studies indicate variable absorption rates across different formulations, necessitating further optimization of drug delivery systems. Moreover, comprehensive toxicological assessments are required to establish safety profiles for human use. Ongoing research is addressing these gaps through structure-activity relationship studies and formulation science approaches.

The versatility of N-Benzylquinine chloride extends to its potential as a chiral auxiliary in asymmetric synthesis. Its rigid molecular framework and multiple functional groups make it an attractive candidate for catalyzing stereoselective reactions, particularly in the synthesis of complex natural products and pharmaceutical intermediates. Recent applications in total synthesis campaigns have demonstrated its utility in constructing challenging molecular architectures with high enantioselectivity.

Looking forward, the research community anticipates expanded investigations into the therapeutic potential of N-Benzylquinine chloride analogs. Computational modeling and artificial intelligence approaches are being employed to predict novel derivatives with enhanced biological activities and improved drug-like properties. These efforts, combined with continued experimental validation, are expected to yield next-generation therapeutics based on this promising chemical scaffold.

Recommended suppliers
Amadis Chemical Company Limited
(CAS:67174-25-8)N-Benzylquinine chloride
A867326
Purity:99%
Quantity:25g
Price ($):170.0
Email