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Quinoline
Quinoline chemical structure part1.png
Quinoline chemical structure part2.png
IUPAC name
Other names 1-benzazine, 1-azanaphthalene, benzo[b]pyridine
Identifiers
CAS number 91-22-5 Yes check.svgY
SMILES
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
 Yes check.svgY (what is this?)  (verify)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Quinoline is a heterocyclic aromatic organic compound. It has the formula C9H7N and is a colourless hygroscopic liquid with a strong odour. 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.

Quinoline is mainly used as a building block to other specialty chemicals. Approximately 4 tonnes are produced annually according to a report published in 2005. 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".[1]

Contents

Isolation and synthesis

Quinoline was first extracted from coal tar in 1834 by Friedlieb Ferdinand Runge.[2] Coal tar remains the principal source of commercial quinoline. It can be synthesized using various methods:

See also

Safety

Quinoline has an LD50 = 331mg/kg (oral dose for rats). [3]

References

  1. ^ Gerd Collin, Hartmut Höke "Quinoline and Isoquinoline" Ullmann's Encyclopedia of Chemical Technology; 2005 Wiley-VCH, Weinheim. doi:10.1002/14356007.a22_465
  2. ^ "Quinoline". Encyclopedia Britannica. 1911. http://www.1911encyclopedia.org/Quinoline.  
  3. ^ Wolfram|Alpha™

External links

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1911 encyclopedia

Up to date as of January 14, 2010
(Redirected to Database error article)

From LoveToKnow 1911

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