Quinoline

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. Over 200 biologically active quinoline and quinazoline alkaloids are identified. 4-Hydroxy-2-alkylquinolines (HAQs) are involved in antibiotic resistance.

Not to be confused with quinolone.
See also: Quinoline Yellow
Quinoline
Names
Preferred IUPAC name
Quinoline
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
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 Y
    Key: SMWDFEZZVXVKRB-UHFFFAOYSA-N Y
  • 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)
−86.0·10−6 cm3/mol
Thermochemistry
174.9 kJ·mol−1
Hazards
GHS labelling:
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)
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).
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Infobox references
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