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
• Uses: 2,2'-Biquinoline is used as a reagent for spectrophotometric determination of Cu and as an indicator for titration of organolithium reagents, giving yellow-green charge-transfer complexes.

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

2,3-Dihydro-2-[1-[3-phenyl-3-(4-propylphenyl)propyl]-4-piperidinyl]-1H-isoindol-1-one, monohydrochloride

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

Refernces

• 1、 Aksenov,Goncharov. "Heterogenous catalytic method for the synthesis of biquinolines and bipyridines". . p. 1491 - 1492. Retrieved 2008.
• 2、 Wakabayashi, Shoji,Kubo, Yukihiro,Takeda, Takashi,Uenishi, Jun-ichi,Oae, Shigeru. "Synthesis and Reaction of 2,2'-Biquinolyl". . p. 2338 - 2341. Retrieved 1989.
• 3、 Dumouchel, Sylvain,Mongin, Florence,Trécourt, Fran?ois,Quéguiner, Guy. "First cross-coupling reactions of arylmagnesates: A convenient access to heteroarylquinolines". . p. 3877 - 3880. Retrieved 2003.
• 4、 Iyoda,Otsuka,Sato,Nisato,Oda. "Homocoupling of aryl halides using Nickel(II) complex and zinc in the presence of Et4NI. An efficient method for the synthesis of biaryls and bipyridines". . p. 80 - 87. Retrieved 1990.
• 5、 Zelewsky, Alex,Gremaud, Gabriel. "Ruthenium(II) Complexes with Three Different Diimine Ligands". . p. 1108 - 1115. Retrieved 1988.
• 6、 Rapoport et al.. "-". . p. 372. Retrieved 1960.
• 7、 Cao, Yue,Wu, Yong,Zhang, Yuanteng,Zhou, Jing,Xiao, Wei,Gu, Dong. "Highly Ordered Mesoporous Cobalt Oxide as Heterogeneous Catalyst for Aerobic Oxidative Aromatization of N-Heterocycles". . p. 3679 - 3686. Retrieved 2021/06/18.
• 8、 Fukazawa, Yasuaki,Rubtsov, Aleksandr E.,Malkov, Andrei V.. "A Mild Method for Electrochemical Reduction of Heterocyclic N-Oxides". supporting information. p. 3317 - 3319. Retrieved 2020/05/25.