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| Names | |||
|---|---|---|---|
| Preferred IUPAC name Quinoline[2] | |||
Systematic IUPAC name
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Other names
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| Identifiers | |||
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3D model (JSmol) | |||
| 107477 | |||
| ChEBI | |||
| ChEMBL | |||
| ChemSpider |
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| ECHA InfoCard | 100.001.865 | ||
| EC Number |
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| 27201 | |||
| KEGG |
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| MeSH | Quinolines | ||
| RTECS number |
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| UNII | |||
| UN number | 2656 | ||
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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: | |||
   | |||
| 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) | 331 mg/kg | ||
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |||
Quinoline is aheterocyclicaromaticorganic compound with the chemical formula C9H7N. It is a colorlesshygroscopic 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 itsderivatives are useful in diverse applications. A prominent example isquinine, analkaloid found in plants. Over 200 biologically active quinoline andquinazoline alkaloids are identified.[5][6]4-Hydroxy-2-alkylquinolines (HAQs) are involved inantibiotic resistance.
Quinoline was first extracted fromcoal tar in 1834 by German chemistFriedlieb Ferdinand Runge;[4] he called quinolineleukol ("white oil" in Greek).[7] Coal tar remains the principal source of commercial quinoline.[8] In 1842, French chemistCharles Gerhardt obtained a compound by dry distillingquinine,strychnine, orcinchonine withpotassium hydroxide;[4] he called the compoundChinoilin orChinolein.[9] Runge's and Gephardt's compounds seemed to be distinctisomers because they reacted differently. However, the German chemistAugust 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 insectOreophoetes 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 aspyridine derivatives, quinoline is often reported as an environmental contaminant associated with facilities processingoil 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 asRhodococcus species Strain Q1, which was isolated from soil and paper mill sludge.[12]
Quinolines are present in small amounts in crude oil within the virgindiesel fraction. It can be removed by the process calledhydrodenitrification.
Quinolines are often synthesized from simple anilines using a number ofnamed reactions.
Going clockwise from top these are:
A number of other processes exist, which require specifically substituted anilines or related compounds:
Quinolines are reduced totetrahydroquinolines enantioselectively using several catalyst systems.[13][14]
Quinolines are used in the manufacture ofdyes and the preparation ofhydroxyquinoline sulfate andniacin. It is also used as a solvent forresins andterpenes.
Quinoline is mainly used as in the production of otherspecialty chemicals. Approximately 4tonnes were produced annually according to a report published in 2005.[8] Its principal use is as a precursor to8-hydroxyquinoline, which is a versatile chelating agent and precursor to pesticides. Its2- and4-methyl derivatives are precursors tocyanine dyes. Oxidation of quinoline affordsquinolinic acid (pyridine-2,3-dicarboxylic acid), a precursor to the herbicide sold under the name "Assert".[8]
The reduction of quinoline withsodium borohydride in the presence ofacetic acid is known to produceKairoline A.[15] (Cf.Kairine)
Severalanti-malarial drugs contain quinoline substituents. These includequinine,chloroquine,amodiaquine, andprimaquine.
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.
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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