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Quinoline

Not to be confused with quinolone.
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Quinoline[1]
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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
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This page is a soft redirect.- 3DMet B00959 91-22-5 7pxY ChEBI CHEBI:17362 7pxY ChEMBL ChEMBL14474 7pxY ChemSpider 6780 7pxY EC number 202-051-6 Jmol-3D images Image KEGG C06413 7pxY MeSH Quinolines PubChem Template:Chembox PubChem/format RTECS number VA9275000 Template:Chembox UNII UN number 2656 colspan=2 style="background:#f8eaba; border-top:2px solid transparent; border-bottom:2px solid transparent; text-align:center;" #REDIRECTmw:Help:Magic words#Other
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C9H7N Molar mass 129.16 g/mol Appearance yellowish oily liquid Density 1.093 g/mL Melting point Script error: No such module "convert". Boiling point Script error: No such module "convert". /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] colspan=2 style="background:#f8eaba; border-top:2px solid transparent; border-bottom:2px solid transparent; text-align:center;" #REDIRECTmw:Help:Magic words#Other
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R-phrases R21, R22 S-phrases S26, S27, S28, S29, S30, Template:S31, Template:S32, S33, Template:S34, S35, S36 NFPA 704

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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Quinoline is a heterocyclic aromatic organic compound with the chemical formula C9H7N. It is a colorless hygroscopic liquid with a strong odor. Aged samples, especially if exposed to light, become yellow and later brown. Quinoline is only slightly soluble in cold water but dissolves readily in hot water and most organic solvents. Quinoline itself has few applications, but many of its 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.

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.

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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". Encyclopædia Britannica. 1911. 
  4. ^ a b c Gerd Collin; Hartmut Höke (2005), "Quinoline and Isoquinoline", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a22_465 
  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. doi:10.1016/S0964-8305(96)00032-7. 

External links

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