Quinoline
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| Quinoline | |
|---|---|
| IUPAC name | Quinoline |
| Other names | 1-benzazine, 1-azanaphthalene, benzo[b]pyridine |
| Identifiers | |
| CAS number | |
| SMILES | c1cccc2cccnc12 |
| Properties | |
| Molecular formula | C9H7N |
| Molar mass | 129.16 g/mol |
| Density | 1.093 g/ml |
| Melting point |
−15 °C |
| Boiling point |
238 °C |
| Solubility in water | Soluble |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references | |
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Overview
Quinoline, also known as 1-azanaphthalene, 1-benzazine, or benzo[b]pyridine, is a heterocyclic aromatic organic compound. It has the formula C9H7N and is a colourless hygroscopic liquid with a strong odour.
As it ages, if exposed to light, the liquid tends to become yellow and later brown. It is only slightly soluble in water but dissolves readily in many organic solvents.
Quinoline is an intermediate in metallurgical processes and in dye, polymer, and agrochemical production. It is also a preservative, disinfectant, and solvent.
It is toxic: short-term exposure to the vapour causes irritation of the nose, eyes, and throat as well as dizziness and nausea. Longer-term effects are uncertain, but quinoline has been linked to liver damage.
Isolation and synthesis
Quinoline is naturally found in coal tar and was first extracted from this source in 1834 by F. Runge. It can be prepared 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
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
External links
Acknowledgement and Attribution Regarding Sources of Content
Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .
