Editing Quinoline (section)

{{distinguish|quinolone}}
{{see also|Quinoline Yellow (disambiguation){{!}}Quinoline Yellow}}

{{Chembox
|Watchedfields = changed
|verifiedrevid = 464378790
|ImageFile = Quinoline chemical structure.svg
|ImageSize = 250px
|ImageClass = skin-invert
|ImageFileL1 = Quinoline-3D-balls-2.png
|ImageSizeL1 = 120
|ImageAltL1 = Quinoline molecule
|ImageNameL1 = C=black, H=white, N=blue
|ImageFileR1 = Quinoline-3D-spacefill.png
|ImageSizeR1 = 120
|ImageNameR1 = C=black, H=white, N=blue
|ImageAltR1 = Quinoline molecule
|PIN = Quinoline<ref name=iupac2013>{{cite book | title =  Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = [[Royal Society of Chemistry|The Royal Society of Chemistry]] | date = 2014 | location = Cambridge | pages = 4, 211 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4 | quote = The name ‘quinoline’ is a retained name that is preferred to the alternative systematic fusion names ‘1-benzopyridine’ or ‘benzo[''b'']pyridine’.}}</ref>
|SystematicName = {{unbulleted list|1-Benzopyridine<!-- P-25.2.2.4 -->|Benzo[''b'']pyridine<!-- P-25.3.1.3 -->|<!-- von Baeyer Nomenclature -->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|<!-- Fused Ring Nomenclature -->Benzo[''b'']azine|Benzo[''b'']azabenzene}}
|OtherNames = {{unbulleted list|1-Azanaphthalene|1-Benzazine<!-- not recommended according to 2013 IUPAC recommendations -->|Benzazine|Benzazabenzene|Benzopyridine|1-Benzine|Quinolin|Chinoline|Chinoleine|Chinolin|Leucol|Leukol|Leucoline}}
|Section1 = {{Chembox Identifiers
|CASNo = 91-22-5
|CASNo_Ref = {{cascite|correct|CAS}}
|Beilstein = 107477
|PubChem = 7047
|ChemSpiderID = 6780
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
|EINECS = 202-051-6
|Gmelin = 27201
|UNNumber = 2656
|KEGG = C06413
|KEGG_Ref = {{keggcite|correct|kegg}}
|MeSHName = Quinolines
|ChEBI = 17362
|ChEBI_Ref = {{ebicite|correct|EBI}}
|ChEMBL = 14474
|ChEMBL_Ref = {{ebicite|correct|EBI}}
|RTECS = VA9275000
|SMILES = n1cccc2ccccc12
|SMILES1 = C1=CC=C2C(=C1)C=CC=N2
|StdInChI = 1S/C9H7N/c1-2-6-9-8(4-1)5-3-7-10-9/h1-7H
|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
|StdInChIKey = SMWDFEZZVXVKRB-UHFFFAOYSA-N
|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
|InChI = 1/C9H7N/c1-2-6-9-8(4-1)5-3-7-10-9/h1-7H
|InChIKey = SMWDFEZZVXVKRB-UHFFFAOYAU
|UNII = E66400VT9R
|UNII_Ref = {{fdacite|correct|FDA}}
|3DMet = B00959
}}
|Section2 = {{Chembox Properties
|Formula = C<sub>9</sub>H<sub>7</sub>N
|MolarMass = 129.16{{nbsp}}g/mol
|Appearance = Colorless oily liquid
|Density = 1.093{{nbsp}}g/mL
|MeltingPtC = −15
|BoilingPtC = 237
|BoilingPt_notes =, 760{{nbsp}}mm{{nnbsp}}Hg; {{convert|108|–|110|°C}}, 11{{nbsp}}mm{{nnbsp}}Hg
|Solubility = Slightly soluble
|pKa = 4.85 (conjugated acid)<ref>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.</ref>
|SolubleOther = Soluble in alcohol, ether, and carbon disulfide
|MagSus = −86.0·10<sup>−6</sup>{{nbsp}}cm<sup>3</sup>/mol
}}
|Section3 = {{ Chembox Thermochemistry
|DeltaHf = 174.9{{nbsp}}kJ·mol<sup>−1</sup>
}}
|Section4 = {{Chembox Hazards
|NFPA-H = 2
|NFPA-F = 1
|NFPA-R = 0
|GHSPictograms = {{GHS07}}{{GHS08}}{{GHS09}}
|GHSSignalWord = Danger
|HPhrases = {{H-phrases|302|312|315|319|341|350|411}}
|PPhrases = {{P-phrases|201|202|264|270|273|280|281|301+312|302+352|305+351+338|308+313|312|321|322|330|332+313|337+313|362|363|391|405|501}}
|FlashPtC = 101
|AutoignitionPtC = 400
|LD50 = 331{{nbsp}}mg/kg
}}
| Reference = <ref>{{cite web |url=http://www.chemicalland21.com/industrialchem/organic/QUINOLINE.htm |title=QUINOLINE (BENZOPYRIDINE) |work=Chemicalland21.com |access-date=2012-06-14}}</ref>
}}

'''Quinoline''' is a [[heterocyclic]] [[aromatic]] [[organic compound]] with the chemical formula C<sub>9</sub>H<sub>7</sub>N.  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.<ref name=EB1911>{{cite EB1911 |wstitle=Quinoline |volume=22 |page=759}}</ref> Quinoline itself has few applications, but many of its  [[derivative (chemistry)|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.<ref>{{cite journal |last1=Shang |first1=XF |last2=Morris-Natschke |first2=SL |last3=Liu |first3=YQ |last4=Guo |first4=X |last5=Xu |first5=XS |last6=Goto |first6=M |last7=Li |first7=JC |last8=Yang |first8=GZ |last9=Lee |first9=KH |title=Biologically active quinoline and quinazoline alkaloids part I. |journal=Medicinal Research Reviews |date=May 2018 |volume=38 |issue=3 |pages=775–828 |doi=10.1002/med.21466 |pmid=28902434 |pmc=6421866 }}</ref><ref>{{cite journal |last1=Shang |first1=Xiao-Fei |last2=Morris-Natschke |first2=Susan L. |last3=Yang |first3=Guan-Zhou |last4=Liu |first4=Ying-Qian |last5=Guo |first5=Xiao |last6=Xu |first6=Xiao-Shan |last7=Goto |first7=Masuo |last8=Li |first8=Jun-Cai |last9=Zhang |first9=Ji-Yu |last10=Lee |first10=Kuo-Hsiung |title=Biologically active quinoline and quinazoline alkaloids part II |journal=Medicinal Research Reviews |date=September 2018 |volume=38 |issue=5 |pages=1614–1660 |doi=10.1002/med.21492 |pmid=29485730 |pmc=6105521 }}</ref> [[4-Hydroxy-2-alkylquinoline]]s (HAQs) are involved in [[antibiotic resistance]].