Quinoline

Quinoline^[1]
C=black, H=white, N=blue	C=black, H=white, N=blue
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
CAS Number	91-22-5 ;
3D model (JSmol)	Interactive image; Interactive image;
3DMet	B00959;
Beilstein Reference	107477
ChEBI	CHEBI:17362 ;
ChEMBL	ChEMBL14474 ;
ChemSpider	6780 ;
ECHA InfoCard	100.001.865
EC Number	202-051-6;
Gmelin Reference	27201
KEGG	C06413 ;
MeSH	Quinolines
PubChem CID	7047;
RTECS number	VA9275000;
UNII	E66400VT9R ;
UN number	2656
CompTox Dashboard (EPA)	DTXSID1021798 ;
	InChI InChI=1S/C9H7N/c1-2-6-9-8(4-1)5-3-7-10-9/h1-7H Key: SMWDFEZZVXVKRB-UHFFFAOYSA-N ; InChI=1/C9H7N/c1-2-6-9-8(4-1)5-3-7-10-9/h1-7H Key: SMWDFEZZVXVKRB-UHFFFAOYAU;
	SMILES n1cccc2ccccc12; C1=CC=C2C(=C1)C=CC=N2;
Properties
Chemical formula	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
Solubility in water	Slightly soluble
Solubility	Soluble in alcohol, ether, and carbon disulfide
Acidity (pKa)	4.85 (conjugated acid)
Magnetic susceptibility (χ)	−86.0·10−6 cm3/mol
Thermochemistry
Std enthalpy of; formation (ΔfH⦵298)	174.9 kJ·mol−1
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H302, H312, H315, H319, H341, H350, H411
Precautionary statements	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)
Autoignition; temperature	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 their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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.

^ "QUINOLINE (BENZOPYRIDINE)". Chemicalland21.com. Retrieved 2012-06-14.
^ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. pp. 4, 211. doi:10.1039/9781849733069-FP001 (inactive 2024-06-30). 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'.{{cite book}}: CS1 maint: DOI inactive as of June 2024 (link)
^ 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.
^ Chisholm, Hugh, ed. (1911). "Quinoline" . Encyclopædia Britannica. Vol. 22 (11th ed.). Cambridge University Press. p. 759.
^ Shang, XF; Morris-Natschke, SL; Liu, YQ; Guo, X; Xu, XS; Goto, M; Li, JC; Yang, GZ; Lee, KH (May 2018). "Biologically active quinoline and quinazoline alkaloids part I." Medicinal Research Reviews. 38 (3): 775–828. doi:10.1002/med.21466. PMC 6421866. PMID 28902434.
^ Shang, Xiao-Fei; Morris-Natschke, Susan L.; Yang, Guan-Zhou; Liu, Ying-Qian; Guo, Xiao; Xu, Xiao-Shan; Goto, Masuo; Li, Jun-Cai; Zhang, Ji-Yu; Lee, Kuo-Hsiung (September 2018). "Biologically active quinoline and quinazoline alkaloids part II". Medicinal Research Reviews. 38 (5): 1614–1660. doi:10.1002/med.21492. PMC 6105521. PMID 29485730.

[1] "QUINOLINE (BENZOPYRIDINE)". Chemicalland21.com. Retrieved 2012-06-14.

[iupac2013-2] Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. pp. 4, 211. doi:10.1039/9781849733069-FP001 (inactive 2024-06-30). 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'.{{cite book}}: CS1 maint: DOI inactive as of June 2024 (link)

[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.

[EB1911-4] Chisholm, Hugh, ed. (1911). "Quinoline" . Encyclopædia Britannica. Vol. 22 (11th ed.). Cambridge University Press. p. 759.

[5] Shang, XF; Morris-Natschke, SL; Liu, YQ; Guo, X; Xu, XS; Goto, M; Li, JC; Yang, GZ; Lee, KH (May 2018). "Biologically active quinoline and quinazoline alkaloids part I." Medicinal Research Reviews. 38 (3): 775–828. doi:10.1002/med.21466. PMC 6421866. PMID 28902434.

[6] Shang, Xiao-Fei; Morris-Natschke, Susan L.; Yang, Guan-Zhou; Liu, Ying-Qian; Guo, Xiao; Xu, Xiao-Shan; Goto, Masuo; Li, Jun-Cai; Zhang, Ji-Yu; Lee, Kuo-Hsiung (September 2018). "Biologically active quinoline and quinazoline alkaloids part II". Medicinal Research Reviews. 38 (5): 1614–1660. doi:10.1002/med.21492. PMC 6105521. PMID 29485730.

[1]

[2]

[3]

[4]

[5]

[6]