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Quinoline information


Quinoline[1]
Quinoline molecule
C=black, H=white, N=blue
Quinoline molecule
C=black, H=white, N=blue
Names
Preferred IUPAC name
Quinoline[2]
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 checkY
3D model (JSmol)
  • Interactive image
  • Interactive image
3DMet
  • B00959
Beilstein Reference
107477
ChEBI
  • CHEBI:17362 checkY
ChEMBL
  • ChEMBL14474 checkY
ChemSpider
  • 6780 checkY
ECHA InfoCard 100.001.865 Edit this at Wikidata
EC Number
  • 202-051-6
Gmelin Reference
27201
KEGG
  • C06413 checkY
MeSH Quinolines
PubChem CID
  • 7047
RTECS number
  • VA9275000
UNII
  • E66400VT9R checkY
UN number 2656
CompTox Dashboard (EPA)
  • DTXSID1021798 Edit this at Wikidata
InChI
  • InChI=1S/C9H7N/c1-2-6-9-8(4-1)5-3-7-10-9/h1-7H checkY
    Key: SMWDFEZZVXVKRB-UHFFFAOYSA-N checkY
  • 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)[3]
Magnetic susceptibility (χ)
−86.0·10−6 cm3/mol
Thermochemistry
Std enthalpy of
formation fH298)
174.9 kJ·mol−1
Hazards
GHS labelling:
Pictograms
GHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
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)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
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).
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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.

  1. ^ "QUINOLINE (BENZOPYRIDINE)". Chemicalland21.com. Retrieved 2012-06-14.
  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. 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'.
  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.
  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.

and 21 Related for: Quinoline information

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Quinoline

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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...

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Quinoline alkaloids

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Quinoline alkaloids are naturally occurring chemical compounds from the group of alkaloids, which are chemically derived from quinoline. Some quinoline...

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Quinoline Yellow WS

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Quinoline Yellow WS is a mixture of organic compounds derived from the dye Quinoline Yellow SS (spirit soluble). Owing to the presence of sulfonate groups...

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Quinoline methiodide

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Quinoline methiodide is a quaternary ammonium compound produced by reaction of quinoline with methyl iodide. It has paralyzing effects. Quaternary ammonium...

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Quinoline Yellow

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Quinoline Yellow may refer to two chemically related dyes: Quinoline Yellow SS, a bright yellow dye Quinoline Yellow WS, a yellow food coloring It may...

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Heterocyclic compound

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fused benzene derivatives of pyridine, thiophene, pyrrole, and furan are quinoline, benzothiophene, indole, and benzofuran, respectively. The fusion of two...

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Allura Red AC

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commissioned a study of six food dyes (tartrazine, Allura red, Ponceau 4R, Quinoline Yellow, sunset yellow, carmoisine (dubbed the "Southampton 6")), and sodium...

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Sunset yellow FCF

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using six food additive colours, tartrazine, allura red, ponceau 4R, quinoline yellow WS, sunset yellow and carmoisine (dubbed the "Southampton 6") by...

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Combes quinoline synthesis

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Combes quinoline synthesis is a chemical reaction, which was first reported by Combes in 1888. Further studies and reviews of the Combes quinoline synthesis...

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Lindlar catalyst

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of other "catalyst poisons" have been used, including lead oxide and quinoline. The palladium content of the supported catalyst is usually 5% by weight...

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Isoquinoline

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referred to as "an isoquinoline". It is a structural isomer of quinoline. Isoquinoline and quinoline are benzopyridines, which are composed of a benzene ring...

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Cyanine

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heteroaromatic moiety, such as pyrrole, imidazole, thiazole, pyridine, quinoline, indole, benzothiazole, etc. Cyanines were first synthesized over a century...

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Camps quinoline synthesis

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The Camps quinoline synthesis (also known as the Camps cyclization) is a chemical reaction whereby an o-acylaminoacetophenone is transformed into two...

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Food coloring

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synthetic Indigo Carmine, which is blue Allura Red AC, which is red Quinoline Yellow WS, which is yellow While naturally derived colors, most of which...

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Choisya

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Dazzler = 'Londaz' Choisya ternata Choisya ternata Sundance = 'Lich' Many quinoline alkaloids have been isolated from leaves of Choisya ternata. C. ternata...

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Skraup reaction

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The Skraup synthesis is a chemical reaction used to synthesize quinolines. It is named after the Czech chemist Zdenko Hans Skraup (1850-1910). In the archetypal...

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FQ

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Belgium (former IATA code FQ), a Belgian leisure airline (3-(2-furoyl)-quinoline-2 carboxaldehyde), a fluorogenic amine labeling dye This disambiguation...

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Choisya ternata

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gained the Royal Horticultural Society's Award of Garden Merit. Many quinoline alkaloids have been isolated from leaves of C. ternata. C. ternata contains...

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Quinoline Yellow SS

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Quinoline Yellow SS is a bright yellow dye with green shade. It is insoluble in water, but soluble in nonpolar organic solvents. Quinoline yellow is representative...

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Ponceau 4R

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of a mixture of six food dyes (Tartrazine, Allura Red AC, Ponceau 4R, Quinoline Yellow WS, Sunset Yellow and Carmoisine, dubbed the "Southampton 6") and...

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Quinine

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with its ability to dissolve and metabolize hemoglobin. As with other quinoline antimalarial drugs, the precise mechanism of action of quinine has not...

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