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62-53-3

62-53-3 Structure

62-53-3 Structure
IdentificationMore
[Name]

Aniline
[CAS]

62-53-3
[Synonyms]

AKOS BBS-00003680
AMINOBENZENE
ANILINE
ANILINE OIL
BENZENAMINE
BENZENEAMINE
PHENYLAMINE
ai3-03053
amino-benzen
Aminophen
Anilin
anilin(czech)
Anilina
anilina(italian,polish)
Aniline reagent
aniline(andhomologs)
Aniline(benzenamine)
aniline15
anilineandhomologues
Anyvim
[EINECS(EC#)]

200-539-3
[Molecular Formula]

C6H7N
[MDL Number]

MFCD00007629
[Molecular Weight]

93.13
[MOL File]

62-53-3.mol
Chemical PropertiesBack Directory
[Appearance]

Aniline is a clear, colorless, oily liquid that darkens on exposure to light; with a characteristic amine-like odor.
[Appearance]

colourless liquid
[mp ]

-6.2 °C
[bp ]

184 °C(lit.)
[density ]

1.022 g/mL at 25 °C(lit.)
[vapor density ]

3.22 (185 °C, vs air)
[vapor pressure ]

0.7 mm Hg ( 25 °C)
[refractive index ]

n20/D 1.586(lit.)
[Fp ]

76 °C
[storage temp. ]

2-8°C
[Stability:]

Stable. Incompatible with oxidizing agents, bases, acids, iron and iron salts, zinc, aluminium. Light sensitive. Combustible.
[Water Solubility ]

36 g/L (20 ºC)
[Merck ]

14,659
[BRN ]

605631
[Uses]

A thin, colorless oil prepared by reducing benzene with iron filings in the presence of hydrochloric or acetic acid and then separating the aniline formed by distillation. It is slightly soluble in water but dissolves easily in alcohol, ether, and benzene. Aniline is the base for many dyes used to increase the sensitivity of emulsions.
[Uses]

Rubber accelerators and antioxidants, dyes and intermediates, photographic chemicals (hydro- quinone), isocyanates for urethane foams, pharma- ceuticals, explosives, petroleum refining, dipheny- lamine, phenolics, herbicides, fungicides.
[CAS DataBase Reference]

62-53-3(CAS DataBase Reference)
[NIST Chemistry Reference]

Aniline(62-53-3)
[Storage Precautions]

Light sensitive;Store under nitrogen
[EPA Substance Registry System]

62-53-3(EPA Substance)
Hazard InformationBack Directory
[Chemical Properties]

Aniline was fi rst isolated from the destructive distillation of indigo in 1826 by Otto Unverdorben. Aniline is oily and, although colorless, it slowly oxidizes and turns into a kind of resin in air, giving the sample a red-brown tint. At room temperature, aniline, the simplest aromatic amine, is a clear to slightly yellow, oily liquid that darkens to a brown color on exposure to air. Like most volatile amines, it possesses the somewhat unpleasant odor of rotten fi sh and also has a burning aromatic taste. It has a low vapor pressure at room temperature and ignites readily, burning with a smoky flame. It does not readily evaporate at room temperature. Aniline is slightly soluble in water and mixes readily with most organic solvents. It is synthesized by catalytic hydrogenation of nitrobenzene or by ammonolysis of phenol. Aniline is incompatible with strong acids, strong oxidizers, albumin, and solutions of iron, zinc, aluminum, toluene diisocyanate, and alkalis. It ignites spontaneously in the presence of red fuming nitric acid, and with sodium. Originally, the great commercial value of aniline was due to the readiness with which it yields, directly or indirectly, valuable dyestuffs. Currently, the largest market for aniline is in the preparation of methylene diphenyl diisocyanate (MDI), some 85% of aniline serving this market. In fact, in industry, aniline is an initiator or intermediary in the synthesis of aniline being used as a precursor to more complex chemicals. It is the starting material for many dyestuffs, known as aniline dyes. Its main application is in the manufacture of polyurethane foam, and a wide variety of products, such as MDI, agricultural chemicals, synthetic dyes, antioxidants, stabilizers for the rubber industry, varnishes, explosives, analgesics, and hydroquinone for photographic developing, and as an octane booster in gasoline. Aniline has also been detected in tobacco smoke and exposures to aniline have been reported among workers in related industrial workplaces, hazardous waste sites, and the general population through food and drinking water.
[General Description]

A yellowish to brownish oily liquid with a musty fishy odor. Melting point-6°C; boiling point 184°C; flash point 158°F. Denser than water (8.5 lb/gal) and slightly soluble in water. Vapors heavier than air. Toxic by skin absorption and inhalation. Produces toxic oxides of nitrogen during combustion. Used to manufacture other chemicals, especially dyes, photographic chemicals, agricultural chemicals and others.
[Reactivity Profile]

ANILINE(62-53-3) is a heat sensitive base. Combines with acids to form salts. Dissolves alkali metals or alkaline earth metals with evolution of hydrogen. Incompatible with albumin, solutions of iron, zinc and aluminum, and acids. Couples readily with phenols and aromatic amines. Easily acylated and alkylated. Corrosive to copper and copper alloys. Can react vigorously with oxidizing materials (including perchloric acid, fuming nitric acid, sodium peroxide and ozone). Reacts violently with BCl3. Mixtures with toluene diisocyanate may ignite. Undergoes explosive reactions with benzenediazonium-2-carboxylate, dibenzoyl peroxide, fluorine nitrate, nitrosyl perchlorate, peroxodisulfuric acid and tetranitromethane. Violent reactions may occur with peroxyformic acid, diisopropyl peroxydicarbonate, fluorine, trichloronitromethane (293° F), acetic anhydride, chlorosulfonic acid, hexachloromelamine, (HNO3 + N2O4 + H2SO4), (nitrobenzene + glycerin), oleum, (HCHO + HClO4), perchromates, K2O2, beta-propiolactone, AgClO4, Na2O2, H2SO4, trichloromelamine, acids, FO3Cl, diisopropyl peroxy-dicarbonate, n-haloimides and trichloronitromethane. Ignites on contact with sodium peroxide + water. Forms heat or shock sensitive explosive mixtures with anilinium chloride (detonates at 464° F/7.6 bar), nitromethane, hydrogen peroxide, 1-chloro-2,3-epoxypropane and peroxomonosulfuric acid. Reacts with perchloryl fluoride form explosive products. .
[Air & Water Reactions]

Darkens on exposure to air and light. Polymerizes slowly to a resinous mass on exposure to air and light. Slightly soluble in water.
[Hazard]

An allergen. Toxic if absorbed through the skin. Combustible. Skin irritant. Questionable car- cinogen.
[Health Hazard]

ANILINE is classified as very toxic. Probable oral lethal dose in humans is 50-500 mg/kg for a 150 lb. person. Aniline poisoning is characterized by methemoglobin formation in the blood and resulting cyanosis or blue skin. The formation of methemoglobin interferes with the oxygen-carrying capacity of the blood. The approximate minimum lethal dose for a 150 lb. human is 10 grams. Serious poisoning may result from ingestion of 0.25 mL. People at special risk include individuals with glucose-6-phosphate-dehydrogenase deficiency and those with liver and kidney disorders, blood diseases, or a history of alcoholism.
[Health Hazard]

Exposures to aniline on inhalation, ingestion and/or through skin contact cause adverse health effects. Exposures to liquid aniline cause mild irritation to the skin and eyes. Aniline is a blood toxin and its absorption through the skin and by inhalation of its vapor results in systemic toxicity, damage to the kidney, liver, bone marrow and of methemoglobinemia. The symptoms of poisoning include, but are not limited to, drowsiness, dizziness, severe headache, nausea, tiredness, bluish discoloration of the lips and tongue, loss of appetite, irregular heart beat, mental confusion, and shock. A prolonged period of exposure to the vapor results in respiratory paralysis, convulsions, coma, and death.
[Potential Exposure]

Aniline is widely used as an intermediate in the synthesis of dyestuffs. It is also used in the manufacture of rubber accelerators and antioxidants, pharmaceuticals, marking inks; tetryl, optical whitening agents; photographic developers; resins, varnishes, perfumes, shoe polishes, and many organic chemicals.
[Fire Hazard]

Combustion can produce toxic fumes including nitrogen oxides and carbon monoxide. Aniline vapor forms explosive mixtures with air. ANILINE is incompatible with strong oxidizers and strong acids and a number of other materials. Avoid heating. Hazardous polymerization may occur. Polymerizes to a resinous mass.
[First aid]

If this chemical gets into the eyes, remove any contact lenses at once and irrigate immediately for at least 15 minutes, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts the skin, remove contaminated clothing and wash immediately with soap and water. Seek medical attention immediately. If this chemical has been inhaled, remove from exposure, begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if heart action has stopped. Transfer promptly to a medical facility. When this chemical has been swallowed, get medical attention. Give large quantities of water and induce vomiting. Do not make an unconscious person vomit.
[Shipping]

UN1547 Aniline, Hazard Class: 6.1; Labels: 6.1- Poisonous materials. UN1548 Aniline hydrochloride, Hazard Class: 6.1; Labels: 6.1-Poisonous materials.
[Incompatibilities]

May form explosive mixture with air. Unless inhibited (usually methanol), aniline is readily able to polymerize. Fires and explosions may result from contact with halogens, strong acids; oxidizers, strong base organic anhydrides; acetic anhydride, isocyanates, aldehydes, sodium peroxide. Strong reaction with toluene diisocyanate. Reacts with alkali metals and alkali earth metals. Attacks some plastics, rubber and coatings; copper and copper alloys.
[Waste Disposal]

Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal. Incineration with provision for nitrogen oxides removal from flue gases by scrubber, catalytic or thermal device.
Safety DataBack Directory
[Hazard Codes ]

T,N,F
[Risk Statements ]

R23/24/25:Toxic by inhalation, in contact with skin and if swallowed .
R40:Limited evidence of a carcinogenic effect.
R41:Risk of serious damage to eyes.
R43:May cause sensitization by skin contact.
R48/23/24/25:Toxic: danger of serious damage to health by prolonged exposure through inhalation, in contact with skin and if swallowed .
R50:Very Toxic to aquatic organisms.
R68:Possible risk of irreversible effects.
R48/20/21/22:Harmful: danger of serious damage to health by prolonged exposure through inhalation, and in contact with skin and if swallowed .
R39/23/24/25:Toxic: danger of very serious irreversible effects through inhalation, in contact with skin and if swallowed .
R11:Highly Flammable.
[Safety Statements ]

S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S27:Take off immediately all contaminated clothing .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S46:If swallowed, seek medical advice immediately and show this container or label .
S61:Avoid release to the environment. Refer to special instructions safety data sheet .
S63:In case of accident by inhalation, remove casualty to fresh air and keep at rest.
S36/37:Wear suitable protective clothing and gloves .
[RIDADR ]

UN 1547 6.1/PG 2
[WGK Germany ]

2
[RTECS ]

BW6650000
[F ]

8-9
[HazardClass ]

6.1
[PackingGroup ]

II
[HS Code ]

29214110
[storage]

Aniline should be kept stored against physical damage in a cool (but not freezing), dry, well-ventilated location, away from smoking areas and fi re hazard. It should be kept separated from incompatibles and the containers should be bonded and grounded for transfer to avoid static sparks
[Precautions]

When using aniline, occupational workers should wear impervious protective clothing, including boots, gloves, laboratory coat, apron or coveralls, chemical safety goggles, and/ or a full face shield as appropriate, to prevent skin contact. Workplace facilities should maintain an eye-wash fountain and quick-drench facilities. Workers should not eat, drink, or smoke in the workplace.
[Safety Profile]

Suspected carcinogen with experimental neoplastigenic data. A human poison by an unspecified route. Poison experimentally by most routes incluhng inhalation and ingestion. Experimental reproductive effects. A skin and severe eye irritant, and a rmld sensitizer. In the body, aniline causes formation of methemoglobin, resulting in prolonged anoxemia and depression of the central nervous system; less acute exposure causes hemolysis of the red blood cells, followed by stimulation of the bone marrow. The liver may be affected with resulting jaundice. Long-term exposure to a d n e dye manufacture has been associated with malignant bladder growths. A common air contaminant, A combustible liquid when exposed to heat or flame. To fight fire, use alcohol foam, CO2, dry chemical. It can react vigorously with oxidizing materials. When heated to decomposition it emits highly toxic fumes of NOx. Spontaneously explosive reactions occur with benzenediazonium-2-carboxylate, dibenzoyl peroxide, fluorine nitrate, nitrosyl perchlorate, red fuming nitric acid, peroxodisulfuric acid, and tetranitromethane. Violent reactions with boron trichloride, peroxyformic acid, dhsopropyl peroxydicarbonate, fluorine, trichloronitromethane (145℃), acetic anhydride, chlorosulfonic acid, hexachloromelamine, (HNO3 + N2O4 + H2SO4), (nitrobenzene + glycerin), oleum, (HCHO + HClO4), perchromates, K2O2, ppropiolactone, AgClO4, Na2On, H2SO4, trichloromelamine, acids, peroxydisulfuric acid, F03Cl, diisopropyl peroxy-dicarbonate, n-haloimides, and trichloronitromethane. Ignites on contact with sodium peroxide + water. Forms heator shock-sensitive explosive mixtures with anhnium chloride (detonates at 240°C/7.6 bar), nitromethane, hydrogen peroxide, 1 -chloro-2,3- epoxypropane, and peroxomonosulfuric acid. Reactions with perchloryl fluoride, perchloric acid, and ozone form explosive products.
[Hazardous Substances Data]

62-53-3(Hazardous Substances Data)
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Nitric acid-->Benzene-->Nitrogen-->Hydrogen-->Nitrobenzene-->Iron oxide
[Preparation Products]

8-Anilino-1-naphthalenesulfonic acid -->Direct Orange S-->Butyl 2-[[3-[[(2,3-dihydro-2-oxo-1H-benzimidazol-5-yl)amino]carbonyl]-2-hydroxy-1-naphthyl]azo]benzoate-->Poly(1,2-dihydro-2,2,4-trimethylquinoline) -->Pigment Red 175-->3-BROMOPYRIDINE-2-CARBOXYLIC ACID-->FLUORESCENT BRIGHTENER 28-->N,N-Bis(cyanoethyl)aniline-->4-N-DECYLANILINE-->4-bromo-2-(trifluoromethyl)quinoline-->Bronze Red-->Aniline hydrochloride-->Reactive Blue 222-->REACTIVE VIOLET 5-->sodium dibenzyl amine enzene sulfonate-->DCHA-->2-CHLOROMALONALDEHYDE-->N-PHENYLISONICOTINAMIDE-->Acid Yellow 79-->Acid Black 26-->UREA, N-(2,6-DIMETHYLPHENYL)-N'-[IMINO(METHYLAMINO)METHYL]--->2 BASIC ORANGE 2-->N-Phenyl-1-naphthylamine-->4-HYDROXY-2-(TRIFLUOROMETHYL)QUINOLINE-->SOLVENT BLACK 5-->Disperse Scarlet S-3GFL-->N,N'-Diphenylurea-->N-(2-Naphthyl)aniline-->Acid Black 234-->LANASOLBLUE3R-->Direct Dark Brown NM-->Direct Bordeaux NGB-->Direct Green 89-->3-Hydroxydiphenylamine -->Phenylhydrazine sulfate -->2,4,6-Trichloroaniline -->2-Anilinoethanol-->Modified MDI-->Sudan I-->N,N-Diphenyl-p-phenylenediamine
Material Safety Data Sheet(MSDS)Back Directory
[msds information]

aniline(62-53-3).msds
Questions And AnswerBack Directory
[Description]

Aniline is the simplest primary aromatic amine and a compound formed by the substitution of a hydrogen atom in the benzene molecule with an amino group. It is colorless oil like flammable liquid with strong odor. When heated to 370 C, it is slightly soluble in water and soluble in ethanol, ether, chloroform and other organic solvents. It becomes brown in the air or under the sun. It can be distilled by steam. A small amount of zinc powder is added to prevent oxidation when it is distilled. The purified aniline can be added 10 ~ 15ppm NaBH4 to prevent oxidation deterioration. The solution of aniline is alkaline.
It is easy to produce salt when it reacts with acid. The hydrogen atoms on its amino groups can be substituted by alkyl or acyl groups to produce second or third grade aniline and acyl aniline. When substitution reaction occurs, the products of ortho and para substituted products are mainly produced. It reacts with nitrite to form diazonium salts, which can be used to produce a series of benzene derivatives and azo compounds.
[Uses]

Aniline is predominantly used as a chemical intermediate for dyes, drugs, explosives, plastics, and photographic and rubber chemicals. Many chemicals can be made from Aniline, including:
  • Isocyanaates for the urethane industry
  • Antioxidants, activators, accelerators, and other chemicals for the rubber industry
  • Indigo, acetoacetanilide, and other dyes and pigments for a variety of applications
  • Diphenylamine for the rubber, petroleum, plastics, agricultural, explosives, and chemical industries
  • Various fungacides and herbicides for the agricultural industry
  • Pharmaceutical, organic chemical, and other products
[Derivatives]

Many industrial feedstocks including N-alkylaniline, alkylaniline, o-nitroaniline, O-benzyl two amine, phenyl hydrazine, cyclohexanamine, etc is derived from Aniline. It can be used as the intermediates of the fungicide sodium p-aminobenzenesulfonate, SSEED, methyl sterilamine, sterilized amine, carbendazim, pyrazinyl, Benzalin, insecticide, pyrazino, pyrazino, pyrazino, pyrazinophos, herbicide methamidine, acetochlor, butachlor, cyclohexanone, imidazolinic acid etc.
[Reaction]

A primary aromatic amine, aniline is a weak base and forms salts with mineral acids such as aniline hydrochloride. PKb = 9.30, 0.2mol aqueous solution PH value 8.1. In acidic solution, nitrous acid converts aniline into a diazonium salt that is an intermediate in the preparation of a great number of dyes and other organic compounds of commercial interest. When aniline is heated with organic acids, it gives amides, called anilides, such as acetanilide from aniline and acetic acid. Monomethylaniline and dimethylaniline can be prepared from aniline and methyl alcohol. Catalytic reduction of aniline yields cyclohexylamine.
Various oxidizing agents convert aniline to quinone, azobenzene, nitrosobenzene, p-aminophenol, and the phenazine dye aniline black. Amino groups can undergo acylation, halogenation, alkylation and diazotization, and the presence of amino groups makes it nucleophiles capable of many nucleophilic reactions, and at the same time activates the electrophilic substitution on aromatic rings.
[Production]

Aniline was first obtained in 1826 by the destructive distillation of indigo. It is named because of the specific indigo-yielding plant “Indigofera anil” (Indigofera suffruticosa); In 1857, W.H.Jr. Perkin made aniline from reduction of nitrobenzene with iron filings using hydrochloric acid as catalyst which is still being used. At present, the methods of aniline production include catalytic vapor phase reduction of nitrobenzene with hydrogen, catalytic reaction of chlorobenzene and ammonolysis of phenol (Japan).
Before 1960s, aniline production was based on coal tar benzene, and now petroleum benzene has been used. At the end of 1990s, the world's aniline production capacity was above 2.5 million t. 50% of the aniline is used in the production of dye intermediates. About 25% aniline is used to produce isocyanate and its copolymers. The remaining (25%) is used for pesticides, gasoline antiknock agents, and photographic materials etc.
[Reduction of nitrobenzene with hydrogen]

Aniline is currently obtained by catalytic hydrogenation of nitrobenzene. The catalyst usually used is Cu-SiO2, which has good selectivity and can successfully reduce nitrobenzene to aniline. It is not easy to produce hydrogenation on benzene core. The reaction is carried out in a fluidized bed reactor. After purification, the hydrogen is heated by the heater to 350~400℃.
And then it is ushered in the evaporator, while nitrobenzene enters the evaporator from the upper trough, and contacts with the hot hydrogen to be gasified and overheat to 180~223 ℃.
The mixed gas enters from the bottom of the fluidized bed and contacts with the copper catalyst loaded on the silica gel in the fluidized bed. The generated crude aniline and water vapor are discharged from the top of the bed. Crude benzylamine is cooled and separated by a condenser, and then finished aniline is rectified.
[Hazards]

The toxicity of Aniline is LD50500mg/kg (dog oral administration), and is a common pollutant in the environment. Aniline has strong toxicity to blood and nerves. It can be absorbed by skin or by respiratory tract to cause toxicity.
The acute (short-term) and chronic (long-term) effects of aniline in humans consist mainly of effects on the lung, such as upper respiratory tract irritation and congestion. Chronic exposure may also result in effects on the blood. Human cancer data are insufficient to conclude that aniline is a cause of bladder tumors while animal studies indicate that aniline causes tumors of the spleen. EPA has classified aniline as a Group B2, probable human carcinogen.
Evidence reported by the National Institute for Occupational Safety and Health (NIOSH) clearly associates the occupational exposure to o-toluidine and aniline with an increased risk of bladder cancer among workers. The risk of bladder cancer is greatest among workers with possible and definite exposures to o-toluidine and aniline, and the risk increases with the duration of exposure.
Spectrum DetailBack Directory
[Spectrum Detail]

Aniline(62-53-3)IR1
Aniline(62-53-3)MS
Aniline(62-53-3)13CNMR
Aniline(62-53-3)1HNMR
Aniline(62-53-3)IR2
Aniline(62-53-3)ESR
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

Aniline, pure, 99.8%(62-53-3)
[Alfa Aesar]

Aniline, ACS, 99+%(62-53-3)
[Sigma Aldrich]

62-53-3(sigmaaldrich)
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