Quinoline

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Not to be confused with quinolone.
Quinoline[1]
Quinoline chemical structure.svg
Quinoline molecule
Quinoline molecule
Names
Preferred IUPAC name
Quinoline[2]
Systematic IUPAC name
  • 1-Benzopyridine
  • Benzo[b]pyridine
  • 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
  • 1-Benzazine
  • Benzazine
  • Benzazabenzene
  • Benzopyridine
  • 1-Benzine
  • Quinolin
  • Chinoline
  • Chinoleine
  • Chinolin
  • Leucol
  • Leukol
  • Leucoline
Identifiers
91-22-5 YesY
3DMet B00959
ChEBI CHEBI:17362 YesY
ChEMBL ChEMBL14474 YesY
ChemSpider 6780 YesY
EC Number 202-051-6
Jmol 3D model Interactive image
KEGG C06413 YesY
MeSH Quinolines
PubChem 7047
RTECS number VA9275000
UNII E66400VT9R YesY
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[3]
Thermochemistry
174.9 kJ mol−1
Hazards
R-phrases R21, R22
S-phrases S26, S27, S28, S29, S30, Template:S31, Template:S32, S33, Template:S34, S35, S36
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 101 °C (214 °F; 374 K)
400 °C (752 °F; 673 K)
Lethal dose or concentration (LD, LC):
331 mg/kg
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY verify (what is YesYN ?)
Infobox references

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[edit]

Quinoline was first extracted from coal tar in 1834 by Friedlieb Ferdinand Runge; he called quinoline leukol ("white oil" in Greek).[4][5] Coal tar remains the principal source of commercial quinoline.[6] In 1842, French chemist Charles Gerhardt obtained a compound by dry distilling quinine, strychnine, or cinchonine with potassium hydroxide; he called the compound Chinoilin or Chinolein.[7] Runge's and Gephardt's compounds seemed to be distinct isomers because they reacted differently. However, the German chemist August Hoffmann eventually recognized that the differences in behaviors were due to the presence of contaminants and that the two compounds were actually identical.[8]

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 its 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.[9]

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

Synthesis[edit]

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

Quinoline from aniline.png

Going clockwise from top these are:

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

Applications[edit]

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.[6] 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".[6]

The reduction of quinoline with sodium borohydride in the presence of acetic acid is known to produce Kairoline A.[10] (C.f. Kairine)

See also[edit]

References[edit]

  1. ^ "QUINOLINE (BENZOPYRIDINE)". Chemicalland21.com. Retrieved 2012-06-14. 
  2. ^ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. pp. 4, 211. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4. The name ‘quinoline’ is a retained name that is preferred to the alternative systematic fusion names ‘1-benzopyridine’ or ‘benzo[b]pyridine’. 
  3. ^ 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.
  4. ^ F. F. Runge (1834) "Ueber einige Produkte der Steinkohlendestillation" (On some products of coal distillation), Annalen der Physik und Chemie, 31 (5) : 65–78 ; see especially p. 68: "3. Leukol oder Weissöl" (3. White oil [in Greek] or white oil [in German]). From p. 68: "Diese dritte Basis habe ich Leukol oder Weissöl genannt, weil sie keine farbigen Reactionen zeigt." (This third base I've named leukol or white oil because it shows no color reactions.)
  5. ^ "Quinoline". Encyclopædia Britannica. 1911. 
  6. ^ 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 
  7. ^ Gerhardt, Ch. (1842) "Untersuchungen über die organischen Basen" (Investigations of organic bases), Annalen der Chemie und Pharmacie, 42 : 310-313. See also: (Editor) (1842) "Chinolein oder Chinoilin" (Quinoline or quinoilin), Annalen der Chemie und Pharmacie, 44 : 279-280.
  8. ^ Initially, Hoffmann thought that Runge's Leukol and Gerhardt's Chinolein were distinct. (See: Hoffmann, August Wilhelm (1843) "Chemische Untersuchungen der organischen Basen im Steinkohlen-Theeröl" (Chemical investigations of organic bases in coal tar oil), Annalen der Chemie und Pharmacie, 47 : 37-87 ; see especially pp. 76-78.) However, after further purification of his Leukol sample, Hoffmann determined that the two were indeed identical. (See: (Editor) (1845) "Vorläufige Notiz über die Identität des Leukols und Chinolins" (Preliminary notice of the identity of leukol and quinoline), Annalen der Chemie und Pharmacie, 53 : 427-428.)
  9. ^ 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. 
  10. ^ GRIBBLE, Gordon W.; HEALD, Peter W. (1975). "Reactions of Sodium Borohydride in Acidic Media; III. Reduction and Alkylation of Quinoline and Isoquinoline with Carboxylic Acids". Synthesis. 1975 (10): 650–652. doi:10.1055/s-1975-23871. ISSN 0039-7881. 

External links[edit]