| Identification | More | [Name]
Quinoline | [CAS]
91-22-5 | [Synonyms]
1-AZANAPHTHALENE
1-BENZAZINE
2,3-BENZOPYRIDINE
AKOS 91715
BENZO[B]PYRIDINE
CHINOLIN
FEMA 3470
QUINOLINE
1-Benzaine
1-Benzine
ai3-01241
B 500
b-500
Chinoleine
chinolin(czech)
Chinoline
Leucol
Leukol
Quinolin
USAF ek-218 | [EINECS(EC#)]
202-051-6 | [Molecular Formula]
C9H7N | [MDL Number]
MFCD00006736 | [Molecular Weight]
129.16 | [MOL File]
91-22-5.mol |
| Chemical Properties | Back Directory | [Description]
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. It 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. | [Appearance]
Quinoline is a colorless liquid with a penetrating
amine odor. Turns brown on exposure to light. | [Melting point ]
-17--13 °C (lit.) | [Boiling point ]
113-114 °C/11 mmHg (lit.)
237 °C (lit.) | [density ]
1.093 g/mL at 25 °C(lit.)
| [vapor density ]
4.5 (vs air)
| [vapor pressure ]
0.07 mm Hg ( 20 °C)
| [FEMA ]
3470 | [refractive index ]
n20/D 1.625(lit.)
| [Fp ]
214 °F
| [storage temp. ]
Store below +30°C. | [solubility ]
6g/l | [form ]
Liquid | [pka]
4.9(at 20℃) | [color ]
Purple to dark grey | [Odor]
Strong, unpleasant. | [PH]
7.3 (5g/l, H2O, 20℃) | [Stability:]
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. | [explosive limit]
1.2-7%(V) | [Odor Type]
medicinal | [Water Solubility ]
slightly soluble | [Sensitive ]
Light Sensitive & Hygroscopic | [Merck ]
14,8068 | [BRN ]
107477 | [Dielectric constant]
2.6（-180℃） | [InChIKey]
SMWDFEZZVXVKRB-UHFFFAOYSA-N | [LogP]
2.04 at 22℃ | [Uses]
Preserving anatomical specimens; manufac-
ture of quinolinol sulfate; niacin and copper-8-
quinolinolate; flavoring.
| [CAS DataBase Reference]
91-22-5(CAS DataBase Reference) | [IARC]
2B (Vol. 121) 2019 | [NIST Chemistry Reference]
Quinoline(91-22-5) | [EPA Substance Registry System]
91-22-5(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R21/22:Harmful in contact with skin and if swallowed .
R38:Irritating to the skin.
R41:Risk of serious damage to eyes.
R68:Possible risk of irreversible effects.
R40:Limited evidence of a carcinogenic effect.
R37/38:Irritating to respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S36:Wear suitable protective clothing .
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) . | [RIDADR ]
UN 2656 6.1/PG 3
| [WGK Germany ]
2
| [RTECS ]
VA9275000
| [F ]
8 | [Autoignition Temperature]
896 °F | [TSCA ]
Yes | [HazardClass ]
6.1 | [PackingGroup ]
III | [HS Code ]
29334900 | [Safety Profile]
Poison by ingestion, subcutaneous, and intraperitoneal routes. Moderately toxic by skin contact. A skin and severe eye irritant. Mutation data reported. Questionable carcinogen with experimental neoplastigenic and tumorigenic data. It can cause retinitis sdar to that caused by naphthalene but without causing opacity of the lens. Combustible when exposed to heat or flame. Its preparation has caused many industrial explosions. Potentially explosive reaction with hydrogen peroxide. Violent reaction with dmtrogen tetraoxide, perchromates. Incompatible with linseed oil + thionyl chloride, maleic anhydride, Unpredctably violent. When heated to decomposition it emits toxic fumes of NOx. | [Hazardous Substances Data]
91-22-5(Hazardous Substances Data) | [Toxicity]
LD50 orally in rats: 460 mg/kg (Smyth) |
| Hazard Information | Back Directory | [General Description]
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. | [Reactivity Profile]
QUINOLINE(91-22-5) is hygroscopic. QUINOLINE(91-22-5) absorbs as much as 22% water. QUINOLINE(91-22-5) is sensitive to light and moisture. QUINOLINE(91-22-5) darkens on storage. This chemical is a weak base. A potentially explosive reaction may occur with hydrogen peroxide. QUINOLINE(91-22-5) reacts violently with dinitrogen tetraoxide. QUINOLINE(91-22-5) also reacts violently with perchromates. QUINOLINE(91-22-5) is incompatible with (linseed oil + thionyl chloride) and maleic anhydride. QUINOLINE(91-22-5) is also incompatible with strong oxidizers and strong acids. This chemical can be unpredictably violent. QUINOLINE(91-22-5) dissolves sulfur, phosphorus and arsenic trioxide. QUINOLINE(91-22-5) may attack some forms of plastics. QUINOLINE(91-22-5) is a preparative hazard. | [Air & Water Reactions]
Hygroscopic. Soluble in water. | [Health Hazard]
Vapors are irritating to nose and throat and may cause headaches, dizziness, and nausea if inhaled. Ingestion causes irritation of mouth and stomach; vomiting may occur. Contact with eyes or skin causes irritation. | [Potential Exposure]
In manufacture of quinoline deriva-
tives (dyes and pesticides); in synthetic fuel manufacture.
Occurs in cigarette smoke. | [First aid]
Move victim to fresh air. Call 911 or emergency
medical service. Give artificial respiration if victim is not
breathing. Do not use mouth-to-mouth method if victim
ingested or inhaled the substance; give artificial respiration
with the aid of a pocket mask equipped with a one-way valve
or other proper respiratory medical device. Administer oxy-
gen if breathing is difficult. Remove and isolate contami-
nated clothing and shoes. In case of contact with substance,
immediately flush skin or eyes with running water for at
least 20 minutes. For minor skin contact, avoid spreading
material on unaffected skin. Keep victim warm and quiet.
Effects of exposure (inhalation, ingestion or skin contact) to
substance may be delayed. Ensure that medical personnel
are aware of the material(s) involved and take precautions to
protect themselves. Medical observation is recommended
for 24 to 48 hours after breathing overexposure, as pulmo-
nary edema may be delayed. As first aid for pulmonary
edema, a doctor or authorized paramedic may consider
administering a drug or other inhalation therapy. | [Shipping]
UN2656 Quinoline, Hazard Class: 6.1; Labels:
6.1-Poisonous materials. | [Incompatibilities]
Reacts, possibly violently, with strong
oxidants, strong acids; perchromates, nitrogen tetroxide;
and maleic anhydride. Keep away from moisture, steam,
and light. Contact with hydrogen peroxide may cause
explosion. Unpredictably violent, this substance has been
the source of various plant accidents. | [Chemical Properties]
colourless to brown liquid | [Chemical Properties]
Quinoline has a heavy, penetrating and nauseating, yet sweet odor of good tenacity. | [Chemical Properties]
Quinoline is a colorless liquid with a penetrating
amine odor. Turns brown on exposure to light. | [Waste Disposal]
Dissolve or mix the material
with a combustible solvent and burn in a chemical incinera-
tor equipped with an afterburner and scrubber. All federal,
state, and local environmental regulations must be observed. | [Occurrence]
Quinoline was discovered in coal tar distillate in 1834 by Runge. It is released to
the environment through natural combustion processes and has been isolated from
air particulates (Dong et al 1977). Quinoline may be a significant aqueous
byproduct of synthetic fuel production (shale oil, coal processing) and from wood
preservation production and use facilities. Small amounts also have been detected
in tobacco smoke (Schmeltz and Hoffmann 1977). | [Definition]
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. | [Definition]
ChEBI: 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. | [Definition]
quinoline: A hygroscopic unpleasant-smelling colourless oily liquid,C9H7N; b.p. 240°C. Its molecules consistof a benzene ring fused to a pyridinering. It 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. It 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. | [Production Methods]
Quinoline may be synthesized by heating aniline with glycerol and nitrobenzene in
sulfuric acid (Skraup method) or by reacting aniline, acetaldehyde, and a formaldehyde
hemiacetal (Windholz et al 1983). Commercial production is by isolation
from coal tar with greater than 100,000 lbs being produced in 1977. Production of
refined quinoline has almost ceased due to low demand (Parris et al 1983). | [Aroma threshold values]
Detection: 710 ppb | [Taste threshold values]
Taste characteristics at 2 to 10 ppm: earthy, musty, nutty, coumarinic with a chemical nuance. | [Synthesis Reference(s)]
Tetrahedron Letters, 29, p. 953, 1988 DOI: 10.1016/S0040-4039(00)82491-0
Chemical and Pharmaceutical Bulletin, 26, p. 1015, 1978 DOI: 10.1248/cpb.26.1015 | [Flammability and Explosibility]
Nonflammable | [Chemical Reactivity]
Reactivity with Water No reaction; Reactivity with Common Materials: Attacks some forms of plastics; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent. | [Industrial uses]
Quinoline is used as a solvent for resins and terpenes. It also is used as an
antimalarial, an antioxidant, a catalyst and as an intermediate in the manufacture
of various products (Parris et al 1983). | [Carcinogenicity]
Liver tumors were observed in
rats administered diets containing 0.05–0.25% quinoline.
The incidence of hepatocellular carcinomas was 3/11 at
0.05%, 3/16 at 0.1%, and 0/19 at 0.25% versus 0/6 in controls.
At 0.25%, most of the rats died within 40 weeks. The
incidences of hemangioendotheliomas were 6/11, 12/16,
18/19, and 0/6, respectively. Hepatocellular carcinomas
and hemangioendotheliomas were seen in livers of rats
fed 500, 1000, or 2500 ppm for 16–40 weeks. Typical
hyperplasias were also observed in the liver. | [Environmental Fate]
biodegradative processes occur under aerobic conditions. Anaerobic degradation
is minimal (Mill et al 1981). Breakdown of quinoline in natural waters has been
correlated with bacterial concentration (Rogers et al 1984). Adsorption was high in
acidic soils (pH<6) and low in basic soils (pH>7). The presence of pyridine
decreased quinoline adsorption on acidic, but not basic, soils. Sorption did not
correlate with organic carbon or clay content (Felice et al 1984). Soil bacteria have
been grown with quinoline as the sole carbon source (Grant and Al-Najjar 1976).
Quinoline did not bioconcentrate to a significant extent in fathead minnows
(Southworth et al 1980). | [Purification Methods]
Dry quinoline with Na2SO4 and distil it from zinc dust in a vacuum. It has also been dried by boiling with acetic anhydride, then fractionally distilled. Calvin and Wilmarth [J Am Chem Soc 78 1301 1956] cooled redistilled quinoline in ice and added enough HCl to form its hydrochloride. Diazotization removed aniline, the diazo compound being broken down by warming the solution to 60o. Non-basic impurities were removed by ether extraction. Quinoline was then liberated by neutralising the hydrochloride with NaOH, then dried with KOH and fractionally distilled at low pressure. Addition of cuprous acetate (7g/L of quinoline) and shaking under hydrogen for 12hours at 100o removed impurities due to the nitrous acid treatment. Finally the hydrogen was pumped off, and the quinoline was distilled. Other purification procedures depend on conversion to the phosphate (m 159o, precipitated from MeOH solution, filtered, washed with MeOH, then dried at 55o) or the picrate (m 201o) which, after recrystallisation, were reconverted to quinoline. The method using the picrate [Packer et al. J Am Chem Soc 80 905 1958] is as follows: quinoline is added to picric acid dissolved in the minimum volume of 95% EtOH, giving yellow crystals which were washed with EtOH, air-dried and crystallised from acetonitrile. These were dissolved in dimethyl sulfoxide (previously dried over 4A molecular sieves) and passed through a basic alumina column, onto which the picric acid is adsorbed. The free base in the effluent is extracted with n-pentane and distilled under vacuum. Traces of solvent can be removed by vapour-phase chromatography. [Moonaw & Anton J Phys Chem 80 2243 1976.] The ZnCl2 and dichromate complexes have also been used [Cumper et al. J Chem Soc 1176 1962]. [Beilstein 20 H 339, 20 I 134, 20 II 222, 20 III/IV 3334, 20/7 V 276.] | [Toxicity evaluation]
Quinoline undergoes Phase I metabolism to form an enamine
oxide, a rapid transitional epoxide, which can then form DNA
adducts. This epoxide is formed on the pyridine moiety of
quinoline. Fluorination at position 3 completely prevents the
mutagenicity of quinoline. The major metabolic enzyme is the
CYP2E1 isoform with the primary end product from this
reaction being 3-hydroxyquinoline. Refer to the sections on ‘Genotoxicity’ and ‘Carcinogenicity’ for more specific descriptions
of quinoline toxicity. The primary and most severe, toxic
outcome following quinoline exposure is genotoxicity followed
by tumor formation. |
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