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Quinoline

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Title: Quinoline  
Author: World Heritage Encyclopedia
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Subject: 8-Hydroxyquinoline, Aminoquinoline, Basic aromatic ring, Conrad–Limpach synthesis, Heterocyclic compound
Collection: Amine Solvents, Hazardous Air Pollutants, Quinolines, Simple Aromatic Rings
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Quinoline

Quinoline[1]
Quinoline molecule
Quinoline molecule
Names
IUPAC name
quinoline
Systematic IUPAC name
  • 2-azabicyclo[4.4.0]deca-1(6),2,4,7,9-pentaene
  • 2-azabicyclo[4.4.0]deca-1,3,5,7,9-pentaene
  • benzo[b]azine
  • benzo[b]azabenzene
Other names
  • 1-azanaphthalene
  • benzo[b]pyridine
  • 1-benzazine
  • benzazine
  • benzazabenzene
  • benzopyridine
  • 1-benzine
  • quinolin
  • chinoline
  • chinoleine
  • chinolin
  • leucol
  • leukol
  • leucoline
Identifiers
 Y
3DMet
ChEBI  Y
ChEMBL  Y
ChemSpider  Y
EC number 202-051-6
Jmol-3D images Image
KEGG  Y
MeSH
PubChem
RTECS number VA9275000
UNII  Y
UN number 2656
Properties
C9H7N
Molar mass 129.16 g/mol
Appearance yellowish oily liquid
Density 1.093 g/mL
Melting point −15 °C (5 °F; 258 K)
Boiling point 237 °C (459 °F; 510 K) /760 mm Hg, 108 to 110 °C/11 mm Hg
Slightly soluble
Solubility Soluble in alcohol, ether, and carbon disulfide
Acidity (pKa) 4.85[2]
Thermochemistry
174.9 kJ mol−1
Hazards
R-phrases R21, R22
S-phrases S26, S27, S28, S29, S30, , , S33, , S35, S36
NFPA 704
1
2
0
Flash point 101 °C (214 °F; 374 K)
400 °C (752 °F; 673 K)
Lethal dose or concentration (LD, LC):
LD50 (Median dose)
331 mg/kg
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 Y  (: Y/N?)

Quinoline is a derivatives are useful in diverse applications. A prominent example is quinine, an alkaloid found in plants. 4-Hydroxy-2-alkylquinolines (HAQs) are involved in antibiotic resistance.

Contents

  • Occurrence and isolation 1
  • Synthesis 2
  • Applications 3
  • See also 4
  • References 5
  • External links 6

Occurrence and isolation

Quinoline was first extracted from coal tar in 1834 by Friedlieb Ferdinand Runge.[3] Coal tar remains the principal source of commercial quinoline.[4]

Like other nitrogen heterocyclic compounds, such as pyridine derivatives, quinoline is often reported as an environmental contaminant associated with facilities processing oil shale or coal, and has also been found at legacy wood treatment sites. Owing to it relatively high solubility in water, quinoline has significant potential for mobility in the environment, which may promote water contamination. Quinoline is readily degradable by certain microorganisms, such as Rhodococcus species Strain Q1, which was isolated from soil and paper mill sludge.[5]

Quinolines are present in small amounts in crude oil within the virgin diesel fraction. It can be removed by the process called hydrodenitriification.

Synthesis

Quinolines are often synthesized from simple anilines using a number of named reactions.

Going clockwise from top these are:

A number of other processes exist, which require specifically substituted anilines or related compounds:

Applications

Quinoline is used in the manufacture of dyes, the preparation of hydroxyquinoline sulfate and niacin. It has also used as a solvent for resins and terpenes.

Quinoline is mainly used as a feedstock in the production of other specialty chemicals. Approximately 4 tonnes are produced annually according to a report published in 2005.[4] Its principal use is as a precursor to 8-hydroxyquinoline, which is a versatile chelating agent and precursor to pesticides. Its 2- and 4-methyl derivatives are precursors to cyanine dyes. Oxidation of quinoline affords quinolinic acid (pyridine-2,3-dicarboxylic acid), a precursor to the herbicide sold under the name "Assert".[4]

See also

References

  1. ^ "QUINOLINE (BENZOPYRIDINE)". Chemicalland21.com. Retrieved 2012-06-14. 
  2. ^ Brown, H.C., et al., in Baude, E.A. and Nachod, F.C., Determination of Organic Structures by Physical Methods, Academic Press, New York, 1955.
  3. ^ "Quinoline".  
  4. ^ a b c Gerd Collin; Hartmut Höke (2005), "Quinoline and Isoquinoline",  
  5. ^ O'Loughlin, Edward J.; Kehrmeyer, Staci R.; Sims, Gerald K. (1996). "Isolation, characterization, and substrate utilization of a quinoline-degrading bacterium". International Biodeterioration & Biodegradation 38 (2): 107.  

External links

  • International Chemical Safety Card 0071
  • New methods of synthesizing quinolines
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