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Names | |||
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Preferred IUPAC name
Quinoline[2] | |||
Systematic IUPAC name
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Other names
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Identifiers | |||
3D model (JSmol)
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3DMet | |||
107477 | |||
ChEBI | |||
ChEMBL | |||
ChemSpider | |||
ECHA InfoCard | 100.001.865 | ||
EC Number |
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27201 | |||
KEGG | |||
MeSH | Quinolines | ||
PubChem CID
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RTECS number |
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UNII | |||
UN number | 2656 | ||
CompTox Dashboard (EPA)
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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: | |||
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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) | |||
Flash point | 101 °C (214 °F; 374 K) | ||
400 °C (752 °F; 673 K) | |||
Lethal dose or concentration (LD, LC): | |||
LD50 (median dose)
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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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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.[4] 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.[5][6] 4-Hydroxy-2-alkylquinolines (HAQs) are involved in antibiotic resistance.
The name 'quinoline' is a retained name that is preferred to the alternative systematic fusion names '1-benzopyridine' or 'benzo[b]pyridine'.
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: CS1 maint: DOI inactive as of June 2024 (link)