Quinoline

Source: Wikipedia, the free encyclopedia.
Not to be confused with quinolone.
See also: Quinoline Yellow
Quinoline[1]
Quinoline molecule
C=black, H=white, N=blue
Quinoline molecule
C=black, H=white, N=blue
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
3D model (
JSmol
)
3DMet
107477
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
 100.001.865 Edit this at Wikidata
EC Number
  • 202-051-6
27201
KEGG
MeSH Quinolines
RTECS number
  • VA9275000
UNII
UN number 2656
  • InChI=1S/C9H7N/c1-2-6-9-8(4-1)5-3-7-10-9/h1-7H checkY
    Key: SMWDFEZZVXVKRB-UHFFFAOYSA-N checkY
  • InChI=1/C9H7N/c1-2-6-9-8(4-1)5-3-7-10-9/h1-7H
    Key: SMWDFEZZVXVKRB-UHFFFAOYAU
  • n1cccc2ccccc12
  • C1=CC=C2C(=C1)C=CC=N2
Properties
C9H7N
Molar mass 129.16 g/mol
Appearance Colorless 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; 108–110 °C (226–230 °F), 11 mm Hg
Slightly soluble
Solubility Soluble in alcohol, ether, and carbon disulfide
Acidity (pKa) 4.85 (conjugated acid)[3]
−86.0·10−6 cm3/mol
Thermochemistry
Std enthalpy of
formation
(ΔfH⦵298)
 174.9 kJ·mol−1
Hazards
GHS labelling:
GHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
Danger
H302, H312, H315, H319, H341, H350, H411
P201, P202, P264, P270, P273, P280, P281, P301+P312, P302+P352, P305+P351+P338, P308+P313, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P391, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
0
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).
checkY verify (what is checkY☒N ?)

Quinoline is a

antibiotic resistance
.

Occurrence and isolation

Quinoline was first extracted from

isomers because they reacted differently. However, the German chemist August Hoffmann eventually recognized that the differences in behaviors was due to the presence of contaminants and that the two compounds were actually identical.[10]
The only report of quinoline as a natural product is from the Peruvian stick insect Oreophoetes peruana. They have a pair of thoracic glands from which they discharge a malodorous fluid containing quinoline when disturbed.[11]

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.[12]

Quinolines are present in small amounts in crude oil within the virgin

hydrodenitrification
.

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:

Quinolines are reduced to tetrahydroquinolines enantioselectively using several catalyst systems.[13][14]

Applications

Quinolines are used in the manufacture of

niacin. It is also used as a solvent for resins and terpenes
.

Quinoline is mainly used as in the production of other

cyanine dyes. Oxidation of quinoline affords quinolinic acid (pyridine-2,3-dicarboxylic acid), a precursor to the herbicide sold under the name "Assert".[8]

The reduction of quinoline with sodium borohydride in the presence of acetic acid is known to produce Kairoline A.[15] (C.f. Kairine)

Several anti-malarial drugs contain quinoline substituents. These include quinine, chloroquine, amodiaquine, and primaquine.

Quinoline is used as a solvent and reagent in organic synthesis.[16]

Quinolinium compounds (e.g. salts) can also be used as corrosion inhibitors and intensifiers.

See also

References

  1. ^ "QUINOLINE (BENZOPYRIDINE)". Chemicalland21.com. Retrieved 2012-06-14.
  2. 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. ^ a b c Chisholm, Hugh, ed. (1911). "Quinoline" . Encyclopædia Britannica. Vol. 22 (11th ed.). Cambridge University Press. p. 759.
  5. PMID 28902434
    .
  6. PMID 29485730
    .
  7. ^ 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.)
  8. ^
    ISBN 978-3527306732
    .
  9. ^ 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.
  10. ^ 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.)
  11. ^ Eisner, T; Morgan, R.C.; Attygalle A.B., Smedley, S.R.; Herath, K.B., Meinwald, J. (1997) “Defensive Production of quinoline by a phasmid insect (Oreophoetes peruana) J. Exp. Biol. 200, 2493–2500.
  12. doi:10.1016/S0964-8305(96)00032-7
    .
  13. ^ Xu, L.; Lam, K. H.; Ji, J.; Wu, J.; Fan, Q.-H.; Lo, W.-H.; Chan, A. S. C. Chem. Commun. 2005, 1390.
  14. ^ Reetz, M. T.; Li, X. Chem. Commun. 2006, 2159.
  15. ISSN 0039-7881
    .
  16. ISBN 9780470842898
    .

External links

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