2,2'-Biquinoline

Base Information

• Chemical Name: 2,2'-Biquinoline
• CAS No.: 119-91-5
• Deprecated CAS: 1204521-35-6
• Molecular Formula: C18H12N2
• Molecular Weight: 256.307
• Hs Code.: 29334990
• European Community (EC) Number: 204-357-5
• NSC Number: 1533
• UNII: 6RO6GA6RP3
• DSSTox Substance ID: DTXSID8059500
• Nikkaji Number: J5.317A
• Wikipedia: 2,2%27-Biquinoline,2'-Biquinoline
• Wikidata: Q3597981
• Mol file: 119-91-5.mol

Synonyms:2,2'-biquinoline

Chemical Property of 2,2'-Biquinoline

Chemical Property:

• Appearance/Colour: slightly yellow to light beige shiny flakes
• Melting Point: 192-195 °C(lit.)
• Refractive Index: 1.6300 (estimate)
• Boiling Point: 456.1 °C at 760 mmHg
• PKA: 2.19±0.61(Predicted)
• Flash Point: 203.6 °C
• PSA: 25.78000
• Density: 1.223 g/cm³
• LogP: 4.45000
• Storage Temp.: Store at +15°C to +25°C.
• Solubility.: 1.02mg/l
• Water Solubility.: Sparingly soluble in water (0.001g/L).
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 256.100048391
• Heavy Atom Count: 20
• Complexity: 297

Purity/Quality:

99% ^*data from raw suppliers

2,2''-Biquinoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Quinolines
• Canonical SMILES: C1=CC=C2C(=C1)C=CC(=N2)C3=NC4=CC=CC=C4C=C3
• General Description: 2,2'-Biquinoline, also known as 2,2'-bichinoline, 2,2'-biquinolyl, 2,2'-diquinoline, 2,2'-diquinolyl, cuproin, or cuproine, is a biquinoline derivative of interest in organic and medicinal chemistry due to its potential applications as an anticancer agent and its utility as a ligand in coordination chemistry. 2,2'-Biquinoline can be synthesized through multicomponent imino-Diels-Alder cycloaddition and intramolecular Friedel-Crafts cyclization, demonstrating its versatility in chemical synthesis. Its structural confirmation is typically achieved via spectroscopic methods such as IR, NMR, and GC-MS.

Technology Process of 2,2'-Biquinoline

There total 61 articles about 2,2'-Biquinoline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

2-Chloroquinoline (612-62-4) → 2,2'-biquinoline (119-91-5)

Guidance literature:

With potassium hydroxide; In water; N,N-dimethyl-formamide; at 35 ℃; for 24h; Inert atmosphere;

DOI:10.1039/c3cy00303e

Reference yield: 94.0%

Quinoline N-oxide (1613-37-2) → 2,2'-biquinoline (119-91-5)

Guidance literature:

With potassium tert-butylate; In N,N-dimethyl-formamide; at 65 ℃; for 3.16667h; Solvent; Reagent/catalyst; Inert atmosphere; Schlenk technique;

DOI:10.1039/c6cc04816a

Reference yield: 91.0%

quinoline (91-22-5) → 2,2'-biquinoline (119-91-5)

Guidance literature:

With 2,2,6,6-tetramethylpiperidinylmagnesium chloride; N,N,N,N,-tetramethylethylenediamine; In toluene; at 60 ℃; for 20h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;

DOI:10.1002/adsc.201500445

upstream raw materials:

quinoline

2-bromoquinoline

1-quinolin-2-yl-ethanone

o-aminobenzaldehyde

Downstream raw materials:

N-(quinoline-2-carbonyl)anthranilic acid

ofloxacin

[Rh(CO)(C₁₈H₁₂N₂)(As(C₆H₅)3)2]⁽¹⁺⁾*ClO₄^(1-)=[Rh(CO)(C₁₈H₁₂N₂)(As(C₆H₅)3)2]ClO₄

[PdCl(2,4,6-tris(trifluoromethyl)phenyl)(biquinolyl)]

Refernces

Synthesis of new diversely linked biquinoline derivatives by multicomponent Imino-Diels-Alder cycloaddition and intramolecular friedel-crafts cyclization

10.1055/s-0029-1218613

The research focuses on the development of new and efficient routes for synthesizing various types of biquinoline derivatives, specifically 2,6′-, 2,7′-, 2,2′-, and 2,8′-biquinolines. These compounds are of significant interest in organic and medicinal chemistry due to their potential applications in drug development, particularly as anticancer agents, and their role as ligands in coordination chemistry. The synthetic methods employed in this study include imino-Diels–Alder cycloaddition reactions and intramolecular Friedel–Crafts cyclization reactions. Key chemicals involved in the synthesis include simple anilines, benzaldehydes, N-vinylpyrrolidin-2-one (NVP), and various substituted quinolines. The researchers also utilized reagents such as bismuth(III) chloride (BiCl3) for catalysis, sulfur for oxidation, and hydrogenation conditions (H2/Pd/C in methanol) for reduction steps. The study successfully synthesized a range of biquinoline derivatives, with detailed characterization of the products through IR, 1H and 13C NMR spectroscopy, and GC-MS analysis, confirming their structures and yielding insights into their stereochemistry.