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A11545 Quinoline, 97%

CAS Number
91-22-5
Synonyms

Stock No. Size Price ($) Quantity Availability
A11545-22 100g 48.20
A11545-36 500g 102.00
A11545-0E 2500g 134.00
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Quinoline, 97%

MDL
MFCD00006736
EINECS
202-051-6

Chemical Properties

Formula
C9H7N
Formula Weight
129.16
Melting point
-15°
Boiling Point
237°
Flash Point
101°(214°F)
Density
1.090
Refractive Index
1.6260
Storage & Sensitivity
Hygroscopic. Light Sensitive. Ambient temperatures.
Solubility
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

Literature References

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.

GHS Hazard and Precautionary Statements

Hazard Statements: H301-H312-H315-H319-H341-H350

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

Precautionary Statements: P201-P202-P264b-P270-P280i-P281-P301+P310-P302+P352-P305+P351+P338-P308+P313-P312-P330-P332+P313-P362-P501c

Obtain special instructions before use. Do not handle until all safety precautions have been read and understood. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Wear eye/face protection. Use personal protective equipment as required. IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. IF ON SKIN: Wash with plenty of soap and water. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF exposed or concerned: Get medical advice/attention. Call a POISON CENTER or doctor/physician if you feel unwell. Rinse mouth. If skin irritation occurs: Take off contaminated clothing and wash before reuse. Dispose of contents/ container to an approved waste disposal plant

Other References

Merck
14,8068
Beilstein
107477
Hazard Class
6.1
Packing Group
III
Harmonized Tariff Code
2933.49
TSCA
Yes
RTECS
VA9275000

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