quinoline
American Heritage Dictionary:
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quin·o·line
(kwĭn'ə-lēn', -lĭn) 
n.
An aromatic organic base, C9H7N, having a pungent tarlike odor, synthesized or obtained from coal tar, and used as a food preservative and in making antiseptics and dyes.
n.
An aromatic organic base, C9H7N, having a pungent tarlike odor, synthesized or obtained from coal tar, and used as a food preservative and in making antiseptics and dyes.
Oxford Dictionary of Chemistry:
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quinoline
A hygroscopic unpleasant-smelling colourless oily liquid, C9H7N; b.p. 240°C. Its molecules consist of a benzene ring fused to a pyridine ring. It occurs in coal tar and bone oil, and is made from phenylamine and nitrobenzene. Quinoline is a basic compound, forming salts with mineral acids and forming quaternary ammonium compounds with haloalkanes. It is used for making medicines and dyes. In quinoline, the nitrogen atom is one atom away from the position at which the rings are fused. In an isomer, isoquinoline, the nitrogen atom is positioned two atoms away from the fused ring.
Quinoline
Wiley Dictionary of Flavors:
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Quinoline
A benzene ring connected at two carbons with a ring made up of three carbons and one nitrogen containing two double bonds.
Saunders Veterinary Dictionary:
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quinoline
A drug used originally as an antimalarial. Some of its derivatives are used as antiprotozoal and topical antifungal agents, e.g. quinuronium sulfate, 4-aminoquinoline, di-iodohydroxyquinoline and clioquinol (iodochlorhydroxyquin).
Wikipedia on Answers.com:
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Quinoline
| Quinoline | |
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Quinoline |
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Other names
1-benzazine, 1-azanaphthalene, benzo[b]pyridine |
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| Identifiers | |
| CAS number | 91-22-5  |
| PubChem | 7047 |
| ChemSpider | 6780 |
| UNII | E66400VT9R |
| KEGG | C06413 |
| ChEBI | CHEBI:17362 |
| ChEMBL | CHEMBL14474 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C9H7N |
| Molar mass | 129.16 g/mol |
| Density | 1.093 g/ml |
| Melting point |
−15 °C |
| Boiling point |
237°C/760mm Hg, 108-110 °C/11mm Hg |
| Solubility in water | Soluble |
| Basicity (pKb) | 4.85[1] |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Quinoline is a heterocyclic aromatic organic compound with the chemical formula C9H7N.
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Contents
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Properties
Quinoline is a colorless hygroscopic liquid with a strong odor. Aged samples, 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.
Derivatives
Chemical derivatives of quinoline, such as quinine, are found naturally in plants as alkaloids. 4-Hydroxy-2-alkylquinolines (HAQs) are involved in antibiotic resistance.
Occurrence and isolation
Quinoline was first extracted from coal tar in 1834 by Friedlieb Ferdinand Runge.[2] Coal tar remains the principal source of commercial quinoline.
Like other nitrogen heterocylic compounds, such as pyridine derivatives, quinoline is often reported as an environmental contaminant associated with facilities processing oil shale or coal, and has also been found at legacy wood treatment sites. Owing to high water solubility quinoline has significant potential for mobility in the environment, which may promote water contamination. Quinoline is readily degradable by certain microorganisms, such as Rhodococcus species Strain Q1, which was isolated from soil and paper mill sludge.[3]
Synthesis
Quinoline can be synthesized using various methods:
- Combes quinoline synthesis using anilines and β-diketones.
- Conrad-Limpach synthesis using anilines and β-ketoesters.
- Doebner-Miller reaction using anilines and α,β-unsaturated carbonyl compounds.
- Friedländer synthesis using 2-aminobenzaldehyde and acetaldehyde.
- Skraup synthesis using ferrous sulfate, glycerol, aniline, nitrobenzene, and sulfuric acid.
- Povarov reaction using an aniline, a benzaldehyde and an activated alkene.
- Camps quinoline synthesis utilizing an o-acylaminoacetophenone and hydroxide
- Knorr quinoline synthesis, using a β-ketoanilide and sulfuric acid.
- Gould-Jacobs reaction starting from an aniline and ethyl ethoxymethylenemalonate
- Niementowski quinoline synthesis, using anthranilic acid and ketones.
Applications
In manufacturing of dyes, preparation of hydroxyquinoline sulfate and niacin. Solvent for resins and terpenes.
Quinoline is mainly used as a building block in the production of other specialty chemicals. Approximately 4 tonnes are produced annually according to a report published in 2005.[citation needed] Its principal use is as a precursor to 8-hydroxyquinoline, which is a versatile chelating agent and precursor to pesticides. Its 2- and 4-methyl derivatives are precursors to cyanine dyes. Oxidation of quinoline affords quinolinic acid (pyridine-2,3-dicarboxylic acid), a precursor to the herbicide sold under the name "Assert".[4]
See also
- Isoquinoline, an analog with the nitrogen atom in position 2.
- Pyridine, an analog without the fused benzene ring.
- Naphthalene, an analog without the nitrogen atom.
- Indole, an analog with only a five-membered nitrogen ring.
- Simple aromatic rings
- Niementowski quinoline synthesis, quinoline derivative synthesis
- Lindlar catalyst, quinoline prevents formation of alkanes
References
- ^ 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.
- ^ "Quinoline". Encyclopædia Britannica. 1911. http://www.1911encyclopedia.org/Quinoline.
- ^ O'Loughlin, Edward J.; Kehrmeyer, Staci R.; Sims, Gerald K. (1996). "Isolation, characterization, and substrate utilization of a quinoline-degrading bacterium". International Biodeterioration & Biodegradation 38 (2): 107. DOI:10.1016/S0964-8305(96)00032-7.
- ^ Gerd Collin, Hartmut Höke "Quinoline and Isoquinoline" in Ullmann's Encyclopedia of Chemical Technology; 2005 Wiley-VCH, Weinheim. doi:10.1002/14356007.a22_465
External links
- International Chemical Safety Card 0071
- Classical methods of synthesizing quinolines
- New methods of synthesizing quinolines
- Quinoline search by Wolfram|Alpha
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Copyrights:
American Heritage Dictionary
The American Heritage® Dictionary of the English Language, Fourth Edition Copyright © 2007, 2000 by Houghton Mifflin Company. Updated in 2009. Published by Houghton Mifflin Company. All rights reserved.
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Oxford Dictionary of Chemistry
A Dictionary of Chemistry. Sixth Edition. Copyright © Market House Books Ltd, 2008. All rights reserved.
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Wiley Dictionary of Flavors
Copyright © 2008 by Wiley-Blackwell. Wiley and the Wiley logo are registered trademarks of John Wiley & Sons, Inc. and/or its affiliates in the United States and other countries. Used here by license. Read more
Saunders Veterinary Dictionary
Saunders Comprehensive Veterinary Dictionary 3rd Edition. Copyright © 2007 by D.C. Blood, V.P. Studdert and C.C. Gay, Elsevier. All rights reserved.
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