Quinoline
Title: Quinoline
CAS Registry Number: 91-22-5
Additional Names: Leucoline; chinoleine; 1-benzazine; benzo[b]pyridine
Molecular Formula: C9H7N
Molecular Weight: 129.16
Percent Composition: C 83.69%, H 5.46%, N 10.84%
Literature References: Occurs in small amounts in coal tar. Prepd by the Skraup synthesis by heating aniline with glycerol and nitrobenzene in presence of sulfuric acid: Clarke, Davis, Org. Synth. coll. vol. I, 478 (2nd ed., 1941) 478; alternate syntheses: Manske, Chem. Rev. 30, 113 (1942); Bergstrom, ibid. 35, 150 (1944). Process based on the interaction of aniline with acetaldehyde and a formaldehyde hemiacetal: Cislak, Wheeler, US 3020281 (1962 to Reilly Tar & Chem.). Toxicity data: Smyth et al., Arch. Ind. Hyg. Occup. Med. 4, 119 (1951).
Properties: Hygroscopic liquid. Absorbs as much as 22% water. Darkens on storage in ordinary, stoppered bottle. Penetrating odor, not as offensive as pyridine. Volatile with steam. d425 1.0900; mp -15°; bp760 237.7°; bp100 163.2°; bp40 136.7°; bp20 119.8°; bp10 103.8°; bp5 89.6°; bp1.0 59.7°. nD20 1.62683. Absorption spectrum: Hantzsch, Ber. 44, 1824 (1911). Weak base (neutral to phenolphthalein), forms water-soluble salts with strong acids: pK 9.5. Difficultly sol in cold water, more easily in hot water. Miscible with alcohol, ether, carbon disulfide. Dissolves sulfur, phosphorus, arsenic trioxide. Protect from light and moisture. LD50 orally in rats: 460 mg/kg (Smyth).
Melting point: mp -15°
Boiling point: bp760 237.7°; bp100 163.2°; bp40 136.7°; bp20 119.8°; bp10 103.8°; bp5 89.6°; bp1.0 59.7°
pKa: pK 9.5
Index of refraction: nD20 1.62683
Density: d425 1.0900
Toxicity data: LD50 orally in rats: 460 mg/kg (Smyth)
 
Derivative Type: Bisulfate
Molecular Formula: C9H9NO4S
Molecular Weight: 227.24
Percent Composition: C 47.57%, H 3.99%, N 6.16%, O 28.16%, S 14.11%
Properties: White to grayish-white, crystalline powder. mp 163-165°. Freely sol in water; one gram dissolves in 50 ml cold, in 9 ml boiling abs alcohol. Protect from light.
Melting point: mp 163-165°
 
Derivative Type: Hydrochloride
Molecular Formula: C9H7N.HCl
Molecular Weight: 165.62
Percent Composition: C 65.27%, H 4.87%, N 8.46%, Cl 21.41%
Properties: White deliquesc crystals. mp 93-94°. Freely sol in water, alcohol, hot benzene, chloroform, sparingly in cold ether. Keep well closed and protected from light.
Melting point: mp 93-94°
 
Derivative Type: Salicylate
Molecular Formula: C16H13NO3
Molecular Weight: 267.28
Percent Composition: C 71.90%, H 4.90%, N 5.24%, O 17.96%
Properties: Reddish-gray crystalline powder. Sol in 80 parts water; freely sol in alcohol, benzene, ether, glycerol, oils. Protect from light.
 
Derivative Type: Tartrate
Molecular Formula: C43H45N3O24
Molecular Weight: 987.82
Percent Composition: C 52.28%, H 4.59%, N 4.25%, O 38.87%
Properties: White crystals, pungent odor, sharp taste. mp 125° (dec). Sol in 80 parts water, 150 parts alcohol. Insol in ether.
Melting point: mp 125° (dec)
 
Use: Manuf dyes; prepn hydroxyquinoline sulfate, niacin. As preservative for anatomical specimens. Solvent for resins, terpenes.
Therap-Cat: Antimalarial.
Keywords: Antimalarial.

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