Difference between revisions of "Quinoline"

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Latest revision as of 18:21, 15 March 2020

Quinoline
Names
IUPAC name
Quinoline
Systematic IUPAC name
1-Benzopyridine
Other names
2-Azabicyclo[4.4.0]deca-1,3,5,7,9-pentaene
1-Azanaphthalene
1-Benzazine
1-Benzine
Benzazabenzene
Benzazine
Benzo[b]azine
Benzopyridine
Chinoleine
Chinoline
Leucoline
Leukol
Properties
C9H7N
Molar mass 129.16 g/mol
Appearance Colorless to yellowish oily liquid
Odor Penetrating, fish-like
Density 1.093 g/cm3 (20 °C)
Melting point −15 °C (5 °F; 258 K)
Boiling point 237.7 °C (459.9 °F; 510.8 K)
0.61 g/100 ml (20 °C)
Solubility Miscible with acetone, benzene, carbon disulfide, diethyl ether, ethanol
Vapor pressure 0.06 mm Hg at 25 °C
Thermochemistry
174.9 kJ/mol
Hazards
Safety data sheet Sigma-Aldrich
Flash point 101 °C (214 °F; 374 K)
Lethal dose or concentration (LD, LC):
262 mg/kg (rat, oral)
Related compounds
Related compounds
Pyridine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Quinoline is a heterocyclic aromatic organic compound with the chemical formula C9H7N.

Properties

Chemical

Oxidation of quinoline with potassium permanganate yields quinolinic acid (pyridine-2, 3-dicarboxylic acid).

The reduction of quinoline with sodium borohydride in the presence of acetic acid gives Kairoline A.

Physical

Quinoline is a colorless liquid, that darkens upon contact with air. It is not miscible with water, but more miscible with organic solvents. Its odor is similar to most amines, though not as unpleasant as pyridine.

Availability

Quinoline is sold by chemical suppliers.

Preparation

Quinoline can be prepared from aniline and glycerol via the Skraup reaction.

Projects

  • Preparation of 8-Hydroxyquinoline
  • Preparation of quinolinic acid
  • Preparation of quinine

Handling

Safety

Quinoline is irritant and should be handled with care.

Storage

In closed bottles, away from light and air.

Disposal

Can be neutralized with Fenton's reagent.

Can also be destroyed by incineration in a special oven.

References

Relevant Sciencemadness threads