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QUINOLINE

CAS NUMBER: 91-22-5

EC NUMBER: 202-051-6

MOLECULAR FORMULA: C9H7N

MOLECULAR WEIGHT: 129.16


Quinoline is a heterocyclic aromatic organic compound with the chemical formula C9H7N. 
Quinoline is a colorless hygroscopic liquid with a strong odor. 
Aged samples, especially if exposed to light, become yellow and later brown. 

Quinoline is only slightly soluble in cold water but dissolves readily in hot water and most organic solvents. 
Quinoline itself has few applications, but many of its derivatives are useful in diverse applications. 

A prominent example is quinine, an alkaloid found in plants. 
Over 200 biologically active quinoline and quinazoline alkaloids are identified. 
Quinolines are involved in antibiotic resistance.

Quinoline appears as a colorless liquid with a peculiar odor. 
Slightly denser than water. 

Contact may irritate to skin, eyes, and mucous membranes. May be toxic by ingestion. 
Used to make other chemicals.

Quinoline is used mainly as an intermediate in the manufacture of other products. 
Potential exposure to quinoline may occur from the inhalation of cigarette smoke. 

Quinoline breaks down quickly in the atmosphere and water. 
Quinoline is the simplest member of the quinoline class of compounds, comprising a benzene ring ortho fused to C-2 and C-3 of a pyridine ring. 

Quinoline is a mancude organic heterobicyclic parent, a member of quinolines, an azaarene and an ortho-fused heteroarene.
Quinoline, any of a class of organic compounds of the aromatic heterocyclic series characterized by a double-ring structure composed of a benzene and a pyridine ring fused at two adjacent carbon atoms. 
The benzene ring contains six carbon atoms, while the pyridine ring contains five carbon atoms and a nitrogen atom. 

The simplest member of the quinoline family is quinoline itself, a compound with molecular structure C9H7N.
Quinoline is a heterocyclic aromatic organic compound with the chemical formula C9H7N.

Quinolines have antiseptic, antipyretic, and antiperiodic properties and are used as antimalarials and for preparing other antimalarial drugs.

Quinoline can appear as a contaminant in dispersing agents. 
In order to aid the dyeing process, disperse and vat dyes are formulated with dispersing agents. 

Quinolines are a commonly used class of
dispersing agents. These condensates are manufactured from naphthalene, and a minor by-product in the processing of naphthalene is quinoline. 

This can carry through the manufacturing of the naphthalenesulfonate formaldehyde condensate dispersing agents. 
In addition to the manufacture of dispersing agents and dyes, quinoline also has biocidal properties and so may also be used as a fungicide

Quinoline is a colorless liquid with a strong odor. 
Quinoline is a contaminant in some dispersing agents for dyestuffs. 
Quinoline is a colourless hygroscopic liquid with characteristic odour. 

On exposure to light, it turns brown in colour. 
Quinoline decomposes on heating, and on burning produces toxic fumes including nitrogen oxides. 

Quinoline reacts with strong oxidants, acids, and anhydrides. 
Quinoline is only slightly soluble in cold water but dissolves readily in hot water and most organic solvents. 

Quinoline is combustible. 
Quinoline gives off irritating or toxic fumes (or gases) in a fire. 

Quinoline is incompatible with strong acids, oxidisers, dinitrogen tetroxide, linseed oil, thionyl chloride, maleic anhydride, and perchromates and reacts violently with most incompatibles. 
Quinoline is used extensively in the manufacturing of dyes, preparation of hydroxyquinoline sulphate and niacin, as a solvent for resins and terpenes, and as an intermediate in the manufacture of other products.

Quinoline is used mainly as an intermediate in the manufacture of other several products, as a catalyst, as a corrosion inhibitor, in metallurgical processes, in the manufacture of dyes, as a preservative for anatomical specimens, in polymers and agricultural chemicals, and as a solvent for resins and terpenes. 

Quinoline is also used as an anti-malarial medicine. 
Because of its solubility in water, quinoline has significant potential for mobility in the environment, which may promote water contamination. 

Potential exposure to quinoline also occurs from the inhalation of cigarette smoke. 

Quinoline breaks down quickly in the atmosphere and water.
A colorless two-ring heterocyclic compound with an unpleasant odor, which acts as a base and forms salts with acids. First made from the alkaloid quinine, it is found in bone oil and coal tar and used for making drugs and dyestuffs.
A hygroscopic unpleasant-smelling colourless oily liquid,C9H7N; b.p. 240°C. 

Quinolines molecules consistof a benzene ring fused to a pyridinering. 
Quinoline occurs in coal tar andbone oil, and is made from phenylamineand nitrobenzene. 
Quinolineis a basic compound, forming saltswith mineral acids and forming quaternaryammonium compounds withhaloalkanes. 

Quinoline is used for makingmedicines and dyes. 
In quinoline, thenitrogen atom is one atom awayfrom the position at which the ringsare fused. 
In an isomer, isoquinoline,the nitrogen atom is positioned twoatoms away from the fused ring.

 

USES OF QUINOLINE:

Quinoline is used principally for the manufacture of nicotinic acid, which prevents pellagra in humans, and other chemicals. 
Several methods are known for its preparation, and production of synthetic quinoline exceeds that from coal tar.

Quinoline and its derivatives are widely used as fungicides, biocides, antibiotics, alkaloids, dyes, rubber chemicals, and flavoring agents.
Additional industrial applications include their use as corrosion inhibitors, preservatives, and as solvents for resins and terpenes, and in transition-metal complex catalysis for uniform polymerization and luminescence chemistry. 
They are also used in manufacturing oil soluble dyes, food colorants, pharmaceuticals, pH indicators and other organic compounds. 

Quinoline is a catabolite of tryptophan, a fundamental structure in some antihypertensive agents such as the peripheral vasodilators prazosin and doxazosin.
Quinoline is used mainly as an intermediate in the manufacture of other products. 

Quinoline is also used as a catalyst, a corrosion inhibitor, in metallurgical processes, in the manufacture of dyes, as a preservative for anatomical specimens, in polymers and agricultural chemicals, and as a solvent for resins and terpenes. 
Quinoline is also used as an antimalarial medicine.

Quinoline is used in the manufacture of dyesand hydroxyquinoline salts; as a solvent forresins and terpenes; and therapeutically as anantimalarial agent. 
Quinoline occurs in coal tar insmall amounts.

Quinoline is used as an intermediate in the production of quinoline-related compounds (e.g., 8-hydroxyquinoline). 
Quinolines multiple uses include solvent, preservative, flavoring agent in medicine, colorant in dyes and paints, and also a component of some fungicides. 

Quinoline is also a solvent for resins and terpenes and is used in the production of paint. 
Quinoline used as a coloring additive in foods, such as Quinoline Yellow, has increased the concern that quinoline that is found in these processes may contribute to the development of cancers later in life. 

Quinoline is also an antimalarial agent. Sources of quinoline include petroleum and coal processing, wood preservation, and the use of shale oil.

 

APPLICATION OF QUINOLINE:

Quinoline is used in the manufacture of dyes, the preparation of hydroxyquinoline sulfate and niacin. 
Quinoline is also used as a solvent for resins and terpenes.

Quinoline is mainly used as in the production of other specialty chemicals. 
Approximately 4 tonnes are produced annually according to a report published in 2005. 

Quinolines principal use is as a precursor to 8-hydroxyquinoline, which is a versatile chelating agent and precursor to pesticides. 
Quinolines 2- and 4-methyl derivatives are precursors to cyanine dyes. 

Oxidation of quinoline affords quinolinic acid (pyridine-2,3-dicarboxylic acid), a precursor to the herbicide sold under the name "Assert".
The reduction of quinoline with sodium borohydride in the presence of acetic acid is known to produce.

Quinoline has several anti-malarial derivatives, including quinine, chloroquine, amodiaquine, and primaquine.
Quinolines are reduced to tetrahydroquinolines enantioselectively using several catalyst systems.

 

PROPERTIES OF QUINOLINE:

-Quality Level: 200

-grade: reagent grade

-vapor density: 4.5 (vs air)

-vapor pressure: 0.07 mmHg ( 20 °C)

-assay: 98%

-autoignition temp.: 896 °F

-refractive index: n20/D 1.625 (lit.)

-boiling point: 113-114 °C/11 mmHg (lit.) 237 °C (lit.)

-melting point: −17-−13 °C (lit.)

-density: 1.093 g/mL at 25 °C (lit.)

 

PHYSICAL PROPERTIES OF QUINOLINE:

The chemical formula for quinoline is C H N, and it has a molecular weight of 129.15 g/mol. 
Quinoline occurs as a colorless, hygroscopic liquid that darkens with age and is sparingly soluble in water but is more easily soluble in hot water.  

Water solubility at 25°C is 6,110 milligrams per liter (mg/L). 
Quinoline has a penetrating, pungent odor. 
The vapor pressure of quinoline is 0.0091 mm Hg at 25 °C and its log octanol/water partition coefficient(log Kow) is 2.03. 

 

CHEMICAL PROPERTIES OF QUINOLINE:

Quinoline is a colorless liquid with a penetrating amine odor. 
Turns brown on exposure to light.
Quinoline has a heavy, penetrating and nauseating, yet sweet odor of good tenacity.

 

PHYSICAL AND CHEMICAL PROPERTIES OF QUINOLINE:


-Formula: C9H7N

-Molecular mass: 129.2

-Boiling point: 238°C

-Melting point: -15°C

-Relative density (water = 1): 1.09

-Solubility in water, g/100ml at 20°C: 0.61 (very poor)

-Vapour pressure, Pa at 20°C: 8

-Relative vapour density (air = 1): 4.5

-Relative density of the vapour/air-mixture at 20°C (air = 1): 1.00

-Flash point: 101°C c.c.

-Auto-ignition temperature: 480°C

-Explosive limits, vol% in air: 1.2-7

-Octanol/water partition coefficient as log Pow: 2.06


SOURCES OF QUINOLINE:

- Dispersing agents for disperse dyes as an impurity

- Polyester as an impurity

- Some cyanine dyestuffs 


OCCURENCE OF QUINOLINE:

Quinoline was first extracted from coal tar in 1834 by German chemist Friedlieb Ferdinand Runge;[4] he called quinoline leukol ("white oil" in Greek).
Coal tar remains the principal source of commercial quinoline.

In 1842, French chemist Charles Gerhardt obtained a compound by dry distilling quinine, strychnine, or cinchonine with potassium hydroxide; he called the compound Chinoilin or Chinolein. 
Runge's and Gephardt's compounds seemed to be distinct isomers because they reacted differently.
However, the German chemist August Hoffmann eventually recognized that the differences in behaviors was due to the presence of contaminants and that the two compounds were actually identical.

The only report of quinoline as a natural product is from the Peruvian stick insect Oreophoetes peruana. 
They have a pair of thoracic glands from which they discharge a malodorous fluid containing quinoline when disturbed.

Like other nitrogen heterocyclic compounds, such as pyridine derivatives, quinoline is often reported as an environmental contaminant associated with facilities processing oil shale or coal, and has also been found at legacy wood treatment sites. 
Owing to its relatively high solubility in water quinoline has significant potential for mobility in the environment, which may promote water contamination. 

Quinoline is readily degradable by certain microorganisms, such as Rhodococcus species Strain Q1, which was isolated from soil and paper mill sludge.
Quinolines are present in small amounts in crude oil within the virgin diesel fraction. 
Quinoline can be removed by the process called hydrodenitrification.

 

STABILITY OF QUINOLINE:

-Stable. 

-Incompatible with strong acids, strong oxidizing agents. 

-May discolour on exposure to light. 

-Hygroscopic - protect from moisture. 

-Reacts violently and unpredictably with some materials, especially strong oxidizing agents.

 

REACTIVITY PROFILE OF QUINOLINE:

Quinoline is hygroscopic. 
Quinoline absorbs as much as 22% water. 

Quinoline is sensitive to light and moisture. 
Quinoline darkens on storage. 

Quinoline is a weak base. 
A potentially explosive reaction may occur with hydrogen peroxide. 

Quinoline reacts violently with dinitrogen tetraoxide. 
Quinoline also reacts violently with perchromates. 

Quinoline is incompatible with (linseed oil + thionyl chloride) and maleic anhydride. 
Quinoline is also incompatible with strong oxidizers and strong acids. 

Quinoline can be unpredictably violent. 
Quinoline dissolves sulfur, phosphorus and arsenic trioxide. 

Quinoline may attack some forms of plastics. 
Quinoline is a preparative hazard.

 

STORAGE OF QUINOLINE:

-Provision to contain effluent from fire extinguishing. 

-Separated from strong oxidants, acids, acid anhydrides and food and feedstuffs. 

-Keep in the dark. 

-Well closed. 

-Store in an area without drain or sewer access.


SYNONYM:

Chinolin
Chinoline
Quinolin
1-Benzazine
1-Azanaphthalene
Chinoleine
Leucol
Benzo[b]pyridine
Benzopyridine
Leukol
2,3-Benzopyridine
Benzo(b)pyridine
Leucoline
USAF EK-218
1-Benzine
Quinoline-2-D

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