Quinoline

• Catalog No.: A11545
• CAS Number: 91-22-5
• M. F.: C9H7N
• M. W.: 129.15858
• Purity: 97%

SYNONYMS

• Title: 喹啉
• IUPAC name: quinoline
• IUPAC Traditional name: cinch

DATABASE IDS

• EC Number: 202-051-6
• Beilstein Number: 107477
• CAS Number: 91-22-5
• Merck Index: 148068
• MDL Number: MFCD00006736

PROPERTIES

• Purity: 97%
• Boiling Point: 237°C
• Density: 1.090
• Flash Point: 101°C(214°F)
• Melting Point: -15°C
• Refractive Index: 1.6260
• Solubility: More soluble in hot than cold water. Miscible with alcohol, ether
• GHS Hazard statements: H311-H302-H315-H319-H350-H341-H411-H401
• European Hazard Symbols: Toxic (T)
• European Hazard Symbols: Nature polluting (N)
• GHS Precautionary statements: P280-P305+P351+P338-P361-P302+P352-P405-P501A
• Risk Statements: 45-21/22-36/38-68-51/53
• RTECS: VA9275000
• Safety Statements: 53-45-61
• Storage Warning: Light Sensitive & Hygroscopic
• TSCA Listed: 是
• Hazard Class: 6.1
• UN Number: UN2656
• Packing Group: III

REFERENCES

• Dehydrohalogenation base; see, e.g.: Org. Synth. Coll., 4, 608 (1963).
• Widely used solvent for the copper-promoted decarboxylation of carboxylic acids; see, e.g.: Org. Synth. Coll., 4, 731, 857 (1963).
• Reacts with acyl halides in the presence of an alkali cyanide to give Reissert compounds. For reviews, see: Chem. Rev., 55, 511 (1955); Adv. Het. Chem., 9, 1 (1968); 24, 187 (1979). See also Isoquinoline, B21279. For the formation of Reissert compounds under phase-transfer conditions, with a variety of carbonyl, sulfonyl and phosphoryl halides, see: Synthesis, 497 (1977). For 'direct' cyanation by a modified Reissert procedure, using DBU, see: J. Org. Chem., 49, 4056 (1984).
• Enhances selectivity of reduction of alkynes to alkenes over Lindlar catalyst: Org. Synth. Coll., 5, 880 (1973). In combination with sulfur, is a catalyst poison for the Rosenmund reduction of acid chlorides to aldehydes: Org. Synth. Coll., 3, 629 (1955), Note 4.
• Li or Na in liquid ammonia give the 1,4-dihydro-derivative: Tetrahedron Lett., 2395 (1975), whereas pyridine-borane gives 1,2,3,4-tetrahydroquinoline: Synthesis, 447 (1978). Reaction with NaBH₄ and a carboxylic acid results in "reduction-alkylation" to a 1-alkyl-1,2,3,4-tetrahydroquinoline: Synthesis, 650 (1975); compare also Sodium cyanoborohydride, 87839. However, selective hydrogenation of the benzene ring over PtO₂ in conc. HCl was reported: J. Am. Chem. Soc., 96, 2256 (1974).
• A novel radical alkylation of quinoline and related heterocycles in the 2-position uses free radicals generated by reaction of alkyl iodides with hydrogen peroxide in DMSO: J. Org. Chem., 54, 5224 (1989). For silver(II)-promoted radical alkylation, see: Trimethylacetic acid, A10776.