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91-22-5 - Quinoline, 97% - A11545 - Alfa Aesar

A11545 Quinoline, 97%

Numéro de CAS
91-22-5
Synonymes

Conditionnement Prix ($) Quantité Disponibilité
100g 17,70
500g 58,50
2500g 180,00
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Quinoline, 97%

MDL
MFCD00006736
EINECS
202-051-6

Propriétés chimiques

Formule
C9H7N
Poids moleculaire
129.16
Point de fusion
-15°
Point d'ébullition
237°
Point d'éclair
101°(214°F)
Densité
1.090
Indice de réfraction
1.6260
Sensibilité
Light Sensitive & Hygroscopic
Solubilité
More soluble in hot than cold water. Miscible with alcohol, ether

Applications

Quinoline is used as a chemical intermediate for making medicines and other organic compounds.  It acts as a fundamental structure in some antihypertensive agents such as prazosin and doxazosin which are peripheral vasodilator. It is also used in alkaloids, dyes, rubber chemicals and flavoring agents. They are also used as catalyst, corrosion inhibitor, preservative, and as solvent for resins and terpenes. They are used in transition-metal complex catalyst chemistry for uniform polymerization and luminescence chemistry. They are used as antifoaming agent in refinery field.

Notes

Dissolves sulfur, As{2}O{3}, phosphorus

Références bibliographiques

Khan KM.; Saify ZS.; Khan ZA.; Ahmed M.; Saeed M.; Schick M.; Kohlbau HJ.; Voelter W. Syntheses and cytotoxic, antimicrobial, antifungal and cardiovascular activity of new quinoline derivatives. Eur. pubmedcentral.200050, (10), 915-924].

Krzysztof R. Januszkiewicz.; Howard Alper. Exceedingly mild, selective and stereospecific phase-transfer-catalyzed hydrogenation of arenes. Organometallics. 1983, 2, (8), 1055-1057.

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).

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).

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.

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H302-H311-H315-H319-H341-H350

Harmful if swallowed. Toxic in contact with skin. Causes skin irritation. Causes serious eye irritation. Suspected of causing genetic defects. May cause cancer.

Mentions de prudence: P201-P280-P305+P351+P338-P301+P312a-P405-P501a

Obtain special instructions before use. Wear protective gloves/protective clothing/eye protection/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF SWALLOWED: Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Autres références

Merck
14,8068
Beilstein
107477
Classe de danger
6.1
Groupe d'emballage
III
Code tarifaire harmonisé
2933.49
TSCA
Yes
RTECS
VA9275000

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Analytique et matériel de laboratoire