Quinoline

Quinoline
Quinoline
Identifiers
CAS number 91-22-5 YesY
PubChem 7047
ChemSpider 6780 YesY
UNII E66400VT9R N
KEGG C06413 YesY
ChEBI CHEBI:17362 N
ChEMBL CHEMBL14474 YesY
Jmol-3D images Image 1
Properties
Molecular formula C9H7N
Molar mass 129.16 g/mol
Density 1.093 g/ml
Melting point

−15 °C

Boiling point

237°C/760mm Hg, 108-110 °C/11mm Hg

Solubility in water Soluble
Basicity (pKb) 4.85[1]
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Quinoline is a heterocyclic aromatic organic compound. It has the formula C9H7N and is a colourless hygroscopic liquid with a strong odour. Aged samples, 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 is mainly used as a building block to other specialty chemicals. Approximately 4 tonnes are produced annually according to a report published in 2005.[citation needed] 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".[2]

Like other nitrogen heterocylic 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 high water solubility quinoline has significant potential for mobility in the environment, which may promote water contamination. Fortunately, quinoline is readily degradable by certain microorganisms, such as Rhodococcus species Strain Q1, which was isolated from soil and paper mill sludge. [3]

Contents

Isolation and synthesis

Quinoline was first extracted from coal tar in 1834 by Friedlieb Ferdinand Runge.[4] Coal tar remains the principal source of commercial quinoline. It can be synthesized using various methods:

Applications

In manufacturing of dyes, preparation of hydroxyquinoline sulfate and niacin. Solvent for resins and terpenes.

See also

References

  1. ^ 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.
  2. ^ Gerd Collin, Hartmut Höke "Quinoline and Isoquinoline" Ullmann's Encyclopedia of Chemical Technology; 2005 Wiley-VCH, Weinheim. doi:10.1002/14356007.a22_465
  3. ^ O'Loughlin, E.J., S.R. Kehrmeyer, and G.K. Sims. 1996. Isolation, characterization, and substrate utilization of a quinoline degrading bacterium. International Biodeterioration and Biodegradation. 38(2):107-118. doi:10.1016/S0964-8305(96)00032-7
  4. ^ "Quinoline". Encyclopedia Britannica. 1911. http://www.1911encyclopedia.org/Quinoline. 

External links


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Look at other dictionaries:

  • Quinoline — Quin o*line, n. [Quinine + L. oleum oil + ine.] (Chem.) A nitrogenous base, {C9H7N} obtained as a pungent colorless liquid by the distillation of alkaloids, bones, coal tar, etc. It the nucleus of many organic bodies, especially of certain… …   The Collaborative International Dictionary of English

  • quinoline — [kwin′ə lēn΄, kwin′əlin] n. [ QUIN(INE) + OL1 + INE3] 1. a colorless, liquid compound, C9H7N, obtained by the destructive distillation of bones, coal tar, and various alkaloids, or by synthesis: it is used in making antiseptics, dyes, etc. and as …   English World dictionary

  • quinoline — /kwin l een , in/, n. Chem. a colorless, liquid, water immiscible, nitrogenous base, C9H7N, having a disagreeable odor, occurring in coal tar, and usually prepared by oxidizing a mixture of glycerol and aniline: used as a solvent and reagent and… …   Universalium

  • quinoline — noun Etymology: International Scientific Vocabulary quinine + 3 ol + 2 ine Date: 1845 1. a pungent oily nitrogenous base C9H7N obtained usually by distillation of coal tar or by synthesis from aniline that is the parent compound of many alkaloids …   New Collegiate Dictionary

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