ANILINE

Aniline (from Portuguese anil 'indigo shrub', and -ine indicating a derived substance) is an organic compound with the formula C6H5NH2. 
Aniline is a type of organic base which is used in the making of several dyes, explosives, plastics, drugs, and rubber, and photographic chemicals. 
Aniline is an industrially significant commodity chemical, as well as a versatile starting material for fine chemical synthesis. 

CAS Number:  62-53-3
EC Number: 200-539-3
Chemical Formula:  C6H7N
Molar Mass: 93.129 g·mol−1

Aniline is used in rubber accelerators and anti-oxidants, dyes and intermediates, photographic chemicals, as isocyanates for urethane foams, in pharmaceuticals, explosives, petroleum refining; and in production of diphenylamine, phenolics, herbicides and fungicides. 
Aniline is also used in the manufacture of polyurethanes, rubber processing chemicals, pesticides, fibres, dyes and pigments, photographic chemicals, and pharmaceuticals.

Aniline is an aromatic primary amine that may be used as a reactant in the synthesis of organic intermediates such as 3-chloro-N-phenyl-pyridin-2-amine, (Z)-methyl 3-(phenylamino)but-2-enoate, 2-iodo-N-phenylbenzamide, 2,4-dichloroquinoline and N-(2-propynyl)aniline.

Aniline (from Portuguese anil 'indigo shrub', and -ine indicating a derived substance) is an organic compound with the formula C6H5NH2. 
Consisting of a phenyl group (−C6H5) attached to an amino group (−NH2), aniline is the simplest aromatic amine. 

Aniline is an industrially significant commodity chemical, as well as a versatile starting material for fine chemical synthesis. 
Aniline main use is in the manufacture of precursors to polyurethane, dyes, and other industrial chemicals. 

Like most volatile amines, Aniline has the odor of rotten fish. 
Aniline ignites readily, burning with a smoky flame characteristic of aromatic compounds.
Aniline is toxic to humans.

Relative to benzene, Aniline is electron-rich. 
Aniline thus participates more rapidly in electrophilic aromatic substitution reactions. 

Likewise, Aniline is also prone to oxidation: while freshly purified aniline is an almost colorless oil, exposure to air results in gradual darkening to yellow or red, due to the formation of strongly colored, oxidized impurities. 
Aniline can be diazotized to give a diazonium salt, which can then undergo various nucleophilic substitution reactions.

Like other amines, aniline is both a base (pKaH = 4.6) and a nucleophile, although less so than structurally similar aliphatic amines.
Because an early source of the benzene from which they are derived was coal tar, aniline dyes are also called coal tar dyes.

Aniline is a type of organic base which is used in the making of several dyes, explosives, plastics, drugs, and rubber, and photographic chemicals. 
Anilines are the organic compounds that lie in the class of groups coming in the organic chemistry that is referred to as aminobenzene or phenylamine. 

These compounds are known to be toxic and to be one of the classes of the aromatic amines. 
They are used in a variety of industrial applications and possess all the characteristics of that of an aromatic compound. 

The aniline compounds are known to have the formula C6H5NH2 in which the amino group is attached to the phenyl group. 
Aniline occurs in the form of a yellowish and slightly brownish oily liquid which has a fishy and a musty odour. 

Aniline smells like a rotten fish. 
Aniline is a chemical substance that is a flammable liquid and has a very unpleasant odour. 

Aniline of aniline is soluble in water which is colourless to light brown. 
Aniline chemical formula is C6H5NH2 or C6H7N. 

Since Aniline consists of 6 carbon atoms, 7 hydrogen atoms, and 1 nitrogen atom in Aniline chemical formula, Aniline is an organic compound. 
Today, we will learn about what is anilines, the phenylamine structure, Aniline physical properties and uses.

Aniline, an organic base used to make dyes, drugs, explosives, plastics, and photographic and rubber chemicals.

Aniline was first obtained in 1826 by the destructive distillation of indigo. 
Aniline name is taken from the specific name of the indigo-yielding plant Indigofera anil (Indigofera suffruticosa); Aniline chemical formula is C6H5NH2.

Aniline is prepared commercially by the catalytic hydrogenation of nitrobenzene or by the action of ammonia on chlorobenzene. 
The reduction of nitrobenzene can also be carried out with iron borings in aqueous acid.

A primary aromatic amine, aniline is a weak base and forms salts with mineral acids. 
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, Aniline 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.

Pure aniline is a highly poisonous, oily, colourless substance with a pleasant odour.

Aniline is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 1 000 000 tonnes per annum.
Aniline is used at industrial sites and in manufacturing.

Anilines are an organic compound. 
Aniline has a formula C6H5NH2 since Aniline has 6 carbon atoms, 1 nitrogen atom and 7 hydrogen atoms. 

Anilines has a phenyl group attached to an amino group. 
Aniline is the simplest aromatic amine. 

Anilines are an industrially significant commodity chemical. 
Like other volatile amines, Aniline has the odour of rotten fish. 

Aniline ignites easily. 
Aniline burns with a smoky flame characteristic of aromatic compounds.

Chemically, aniline is an electron-rich benzene derivative. 
As a consequence, aniline reacts rapidly in electrophilic aromatic substitution reactions. 

Aniline is also prone to oxidation. 
Freshly purified aniline is a bit colourless oil, on exposure to air results in gradual darkening of the sample (to yellow or red) due to the formation of strongly coloured, oxidized impurities. 

Aniline is diazotized to give a diazonium salt. 
This salt then undergoes various nucleophilic substitution reactions.

Aniline appears as a yellowish to brownish oily liquid with a musty fishy odor. 
Aniline is produces toxic oxides of nitrogen during combustion. 

Aniline is used to manufacture other chemicals, especially dyes, photographic chemicals, agricultural chemicals and others.
Aniline is a clear to slightly yellow liquid with a characteristic odor. 
Aniline does not readily evaporate at room temperature. 

Aniline is slightly soluble in water and mixes readily with most organic solvents. 
Aniline is used to make a wide variety of products such as polyurethane foam, agricultural chemicals, synthetic dyes, antioxidants, stabilizers for the rubber industry, herbicides, varnishes and explosives.

Aniline is an organic chemical compound, specifically a primary aromatic amine. 
Aniline consists of a benzene ring attached to an amino group. 

Aniline is oily and, although colorless, Aniline can be slowly oxidized and resinified in air to form impurities which can give Aniline a red-brown tint. 
Aniline boiling point is 184 degree centigrade and Aniline melting point is -6 degree centegrade. 

Aniline is a liquid at room temperature. 
Like most volatile amines, Aniline possesses a somewhat unpleasant odour of rotten fish, and also has a burning aromatic taste; Aniline is a highly acrid poison. 

Aniline ignites readily, burning with a large smoky flame. 
Aniline reacts with strong acids to form salts containing the anilinium (or phenylammonium) ion (C6H5-NH3+), and reacts with acyl halides (such as acetyl chloride (ethanoyl chloride), CH3COCl) to form amides. 

The amides formed from aniline are sometimes called anilides, for example CH3-CO-NH-C6H5 is acetanilide, for which the modern name is N-phenyl ethanamide. 
Like phenols, aniline derivatives are highly reactive in electrophilic substitution reactions. 
For example, sulfonation of aniline produces sulfanilic acid, which can be converted to sulfanilamide. 

Sulfanilamide is one of the sulfa drugs which were widely used as antibacterial in the early 20th century. 
Aniline was first isolated from the destructive distillation of indigo in 1826 by Otto Unverdorben. 

In 1834, Friedrich Runge isolated from coal tar a substance which produced a beautiful blue color on treatment with chloride of lime; this he named kyanol or cyanol. 
In 1841, C. J. Fritzsche showed that by treating indigo with caustic potash Aniline yielded an oil, which he named aniline, from the specific name of one of the indigo-yielding plants, Indigofera anil, anil being derived from the Sanskrit, dark-blue.

Uses of Aniline:
Aniline is predominantly used for the preparation of methylenedianiline and related compounds by condensation with formaldehyde. 
The diamines are condensed with phosgene to give methylene diphenyl diisocyanate, a precursor to urethane polymers.

Other uses include rubber processing chemicals (9%), herbicides (2%), and dyes and pigments (2%).
As additives to rubber, aniline derivatives such as phenylenediamines and diphenylamine, are antioxidants. 

Illustrative of the drugs prepared from aniline is paracetamol (acetaminophen, Tylenol). 
The principal use of aniline in the dye industry is as a precursor to indigo, the blue of blue jeans.

Aniline is predominantly used as a chemical intermediate for the dye, agricultural, polymer, and rubber industries. 
Aniline is also used as a solvent, and has been used as an antiknock compound for gasolines.

Aniline is used in the synthesis of dyes, rubber additives, drugs, photographic chemicals, isocyanates, and pesticides.

Aniline is used in mmanufacture dyes, medicinals, resins, varnishes, perfumes, shoe blacks; vulcanizing rubber; as solvent. 
Aniline is stable, although small outlet, aniline is mainly used for preparation of analgesics, antipyretics, antiallergics, and vitamins.

Uses at industrial sites:
Aniline is used in the following products: pH regulators and water treatment products.
Aniline has an industrial use resulting in manufacture of another substance (use of intermediates).

Aniline is used for the manufacture of: chemicals.
Release to the environment of Aniline can occur from industrial use: as an intermediate step in further manufacturing of another substance (use of intermediates), for thermoplastic manufacture and manufacturing of Aniline.

Industry Uses:
Brightener
Dye
Heat transferring agent
Intermediate
Intermediates
Lubricating agent
Other (specify)
Processing aids not otherwise specified
Processing aids, not otherwise listed

Consumer Uses:
Dye
Intermediate
Other (specify)

Industrial Processes with risk of exposure:
Shakeout, Cleaning, and Finishing
Leather Tanning and Processing

Activities with risk of exposure:
Smoking cigarettes

Structure of Aniline:

Aryl-N distances:
In aniline, the C−N bond length is 1.41 Å, compared to 1.47 Å for cyclohexylamine, indicating partial π-bonding between N and C.
The C(aryl)-NH2 distance in anilines is highly sensitive to substituent effects. 
This distance is 1.34 Å in 2,4,6-trinitroaniline vs 1.44 Å in 3-methylaniline.

Pyramidalization:
The amine in anilines is a slightly pyramidalized molecule, with hybridization of the nitrogen somewhere between sp3 and sp2. 
The nitrogen is described as having high p character. 
The amino group in aniline is flatter (i.e., Aniline is a "shallower pyramid") than that in an aliphatic amine, owing to conjugation of the lone pair with the aryl substituent. 

The observed geometry reflects a compromise between two competing factors: stabilization of the N lone pair in an orbital with significant s character favors pyramidalization (orbitals with s character are lower in energy), while delocalization of the N lone pair into the aryl ring favors planarity (a lone pair in a pure p orbital gives the best overlap with the orbitals of the benzene ring π system).

Consistent with these factors, substituted anilines with electron donating groups are more pyramidalized, while those with electron withdrawing groups are more planar. 
In the parent aniline, the lone pair is approximately 12% s character, corresponding to sp7.3 hybridization. (For comparison, alkylamines generally have lone pairs in orbitals that are close to sp3.)

The pyramidalization angle between the C–N bond and the bisector of the H–N–H angle is 142.5°.
For comparison, in more strongly pyramidal methylamine, this value is ~125°, while that of formamide has an angle of 180°.

Production of Aniline:
Industrial aniline production involves two steps. 
First, benzene is nitrated with a concentrated mixture of nitric acid and sulfuric acid at 50 to 60 °C to yield nitrobenzene. 
The nitrobenzene is then hydrogenated (typically at 200–300 °C) in the presence of metal catalysts.

The reduction of nitrobenzene to aniline was first performed by Nikolay Zinin in 1842, using inorganic sulfide as a reductant (Zinin reaction). 
The reduction of nitrobenzene to aniline was also performed as part of reductions by Antoine Béchamp in 1854, using iron as the reductant (Bechamp reduction).

Aniline can alternatively be prepared from ammonia and phenol derived from the cumene process.

In commerce, three brands of aniline are distinguished: aniline oil for blue, which is pure aniline; aniline oil for red, a mixture of equimolecular quantities of aniline and ortho- and para-toluidines; and aniline oil for safranine, which contains aniline and ortho-toluidine and is obtained from the distillate (échappés) of the fuchsine fusion.

Related aniline derivatives:
Many analogues of aniline are known where the phenyl group is further substituted. 
These include toluidines, xylidines, chloroanilines, aminobenzoic acids, nitroanilines, and many others. 

They often are prepared by nitration of the substituted aromatic compounds followed by reduction. 
For example, this approach is used to convert toluene into toluidines and chlorobenzene into 4-chloroaniline.
Alternatively, using Buchwald-Hartwig coupling or Ullmann reaction approaches, aryl halides can be aminated with aqueous or gaseous ammonia.

Manufacturing Methods of Aniline:
Nitrobenzene is hydrogenated to aniline, usually in more than 99% yield, using fixed-bed or fluidized-bed vapor-phase processes.
The most effective catalysts for the gas-phase hydrogenation of nitrobenzene seem to be copper or palladium on activated carbon or an oxidic support, in combination with other metals (Pb, V, P, Cr) as modifiers or promoters in order to achieve high activity and selectivity.

The industrial aniline processes of ICI and DuPont involve hydrogenation of nitrobenzene in the liquid phase. 
Liquid-phase hydrogenation processes are operated at 90-200 °C and 100-600 kPa. 

The liquid phase reaction may be carried out in slurry or in fluidized-bed reactors. 
Conversion of nitrobenzene is normally complete after a single reactor pass with yields of 98 to 99%.

In the commercial phenol route developed, phenol is aminated in the vapor phase using ammonia in the presence of a silica-alumina catalyst.
The reaction is mildly exothermic (H = - 8.4 kJ/mol) and reversible, so high conversion is obtained only by the use of excess ammonia (mole ratio of 20:1) and a low reaction temperature, which also reduces the dissociation of ammonia. 

By product impurities include diphenylamine, triphenylamine and carbazole. 
Their formation is also inhibited by the use of excess ammonia. 

Yields based on phenol and ammonia are >/= 96% and 80%, respectively. 
In the process phenol and fresh and recycle ammonia are vaporized separately (to prevent yield losses) and combined in the fixed bed amination reactor (a) containing the silica-alumina catalyst. After the reaction at 370 °C and 1.7 MPa, the gas is cooled, partly condensed and the excess ammonia is recovered in a separation column, compressed and recycled. 

The condensation product is passed through a drying column to remove water and then through a finishing column to separate aniline from residual phenol and impurities in vacuum (less than 80 kPa). 
The phenol, containing some aniline (azeotropic mixture) is recycled.

Manufactured from nitrobenzene or chlorobenzene.

Derivation: 
By (1) catalytic vapor-phase reduction of nitrobenzene with hydrogen; 
(2) reduction of nitrobenzene with iron filings using hydrochloric acid as catalyst; 
(3) catalytic reaction of chlorobenzene and aqueous ammonia; 
(4) ammonolysis of phenol (Japan).

General Manufacturing Information of Aniline:

Industry Processing Sectors:
All Other Basic Organic Chemical Manufacturing
All Other Chemical Product and Preparation Manufacturing
Cyclic Crude and Intermediate Manufacturing
Fabricated Metal Product Manufacturing
Paper Manufacturing
Petrochemical Manufacturing
Plastics Material and Resin Manufacturing
Plastics Product Manufacturing
Rubber Product Manufacturing
Synthetic Dye and Pigment Manufacturing

Reactions of Aniline:
The chemistry of aniline is rich because Aniline has been cheaply available for many years. 
Below are some classes of Aniline reactions.

Oxidation:
The oxidation of aniline has been heavily investigated, and can result in reactions localized at nitrogen or more commonly results in the formation of new C-N bonds. 
In alkaline solution, azobenzene results, whereas arsenic acid produces the violet-coloring matter violaniline. 

Chromic acid converts Aniline into quinone, whereas chlorates, in the presence of certain metallic salts (especially of vanadium), give aniline black. 
Hydrochloric acid and potassium chlorate give chloranil.

Potassium permanganate in neutral solution oxidizes Aniline to nitrobenzene; in alkaline solution to azobenzene, ammonia, and oxalic acid; in acid solution to aniline black. 
Hypochlorous acid gives 4-aminophenol and para-amino diphenylamine.

Oxidation with persulfate affords a variety of polyanilines. 
These polymers exhibit rich redox and acid-base properties.

Electrophilic reactions at ortho- and para- positions:
Like phenols, aniline derivatives are highly susceptible to electrophilic substitution reactions. 
Aniline high reactivity reflects that Aniline is an enamine, which enhances the electron-donating ability of the ring. 
For example, reaction of aniline with sulfuric acid at 180 °C produces sulfanilic acid, H2NC6H4SO3H.

If bromine water is added to aniline, the bromine water is decolourised and a white precipitate of 2,4,6-tribromoaniline is formed. 

To generate the mono-substituted product, a protection with acetyl chloride is required:
The reaction to form 4-bromoaniline is to protect the amine with acetyl chloride, then hydrolyse back to reform aniline.
The largest scale industrial reaction of aniline involves Aniline alkylation with formaldehyde. 

An idealized equation is shown:
2C6H5NH2+CH2O⟶CH2(C6H4NH2)2+H2O

The resulting diamine is the precursor to 4,4'-MDI and related diisocyanates.

Reactions at nitrogen:

Basicity:
Aniline is a weak base. 
Aromatic amines such as aniline are, in general, much weaker bases than aliphatic amines. 
Aniline reacts with strong acids to form the anilinium (or phenylammonium) ion (C6H5−NH+3).

Traditionally, the weak basicity of aniline is attributed to a combination of inductive effect from the more electronegative sp2 carbon and resonance effects, as the lone pair on the nitrogen is partially delocalized into the pi system of the benzene ring. 

Missing in such an analysis is consideration of solvation. 
Aniline is, for example, more basic than ammonia in the gas phase, but ten thousand times less so in aqueous solution.

Acylation:
Aniline reacts with acyl chlorides such as acetyl chloride to give amides. 
The amides formed from aniline are sometimes called anilides, for example CH3−CO−NH−C6H5 is acetanilide. 
At high temperatures aniline and carboxylic acids react to give the anilides.

N-Alkylation:

N-Methylation of aniline with methanol at elevated temperatures over acid catalysts gives N-methylaniline and N,N-dimethylaniline:
C6H5NH2+2CH3OH⟶C6H5N(CH3)2+2H2O

N-Methylaniline and N,N-dimethylaniline are colorless liquids with boiling points of 193–195 °C and 192 °C, respectively. 
These derivatives are of importance in the color industry.

Carbon disulfide derivatives:
Boiled with carbon disulfide, Aniline gives sulfocarbanilide (diphenylthiourea) (CS(NHC6H5)2), which may be decomposed into phenyl isothiocyanate (C6H5CNS), and triphenyl guanidine (C6H5N=C(NHC6H5)2).

Diazotization:
Aniline and its ring-substituted derivatives react with nitrous acid to form diazonium salts. 
Through these intermediates, the amine group can be converted to a hydroxyl (−OH), nitrile (−CN), or halide group (−X, where X is a halogen) via Sandmeyer reactions. 

This diazonium salt can also be reacted with NaNO2 and phenol to produce a dye known as benzeneazophenol, in a process called coupling. 
The reaction of converting primary aromatic amine into diazonium salt is called diazotisation. 
In this reaction primary aromatic amine reacts with sodium nitrile and with 2 moles of HCl which is known as Ice cold mixture because the temperature use to be 0.5 °C and Aniline forms benzene diazonium salt as major product and water and sodium chloride.

Other reactions:
Aniline reacts with nitrobenzene to produce phenazine in the Wohl-Aue reaction. 
Hydrogenation gives cyclohexylamine.

Being a standard reagent in laboratories, aniline is used for many niche reactions. 
Aniline acetate is used in the aniline acetate test for carbohydrates, identifying pentoses by conversion to furfural. 
Aniline is used to stain neural RNA blue in the Nissl stain.

Biochem/physiol Actions of Aniline:
The acute toxicity of aniline involves Aniline activation in vivo to 4-hydroxyaniline and the formation of adducts with hemoglobin. 
In erythrocytes, this is associated with the release of iron and the accumulation of methemoglobin and the development of hemolytic anemia and inflammation of the spleen. 
Tumor formation is often observed in the spleen on prolonged administration.

Physical Properties of Aniline:

The physical properties of Anilines are given below:
Aniline has a boiling of about 184 oC and melting of about -6 o
Aniline is slightly soluble in water and sometimes freely soluble in the chemicals such as alcohol and ether.

Aniline tends to darken when exposed to air and light.
Aniline is said to be weak base and on Aniline reaction with strong acids, Aniline forms anilinium ion -C6H5-NH3+.
Aniline is said to be toxic when Aniline gets inhaled through the air or gets absorbed into the skin as Aniline produces nitrogen oxides which are harmful to the environment.

History of Aniline:
Aniline was first isolated in 1826 by Otto Unverdorben by destructive distillation of indigo.
He called Aniline Crystallin. 

In 1834, Friedlieb Runge isolated a substance from coal tar that turned a beautiful blue color when treated with chloride of lime. 
He named Aniline kyanol or cyanol.

In 1840, Carl Julius Fritzsche (1808–1871) treated indigo with caustic potash and obtained an oil that he named aniline, after an indigo-yielding plant, anil (Indigofera suffruticosa).
In 1842, Nikolay Nikolaevich Zinin reduced nitrobenzene and obtained a base that he named benzidam.
In 1843, August Wilhelm von Hofmann showed that these were all the same substance, known thereafter as phenylamine or aniline.

Synthetic dye industry:
In 1856, while trying to synthesise quinine, von Hofmann's student William Henry Perkin discovered mauveine and went into industry producing the first commercial synthetic dye. 
Other aniline dyes followed, such as fuchsin, safranin, and induline. 

At the time of mauveine's discovery, aniline was expensive. Soon thereafter, applying a method reported in 1854 by Antoine Béchamp, Aniline was prepared "by the ton".
The Béchamp reduction enabled the evolution of a massive dye industry in Germany. 

Today, the name of BASF, originally Badische Anilin- und Soda-Fabrik (English: Baden Aniline and Soda Factory), now the largest chemical supplier, echoes the legacy of the synthetic dye industry, built via aniline dyes and extended via the related azo dyes. 
The first azo dye was aniline yellow.

Developments in medicine:
In the late 19th century, derivatives of aniline such as acetanilide and phenacetin emerged as analgesic drugs, with their cardiac-suppressive side effects often countered with caffeine.
During the first decade of the 20th century, while trying to modify synthetic dyes to treat African sleeping sickness, Paul Ehrlich – who had coined the term chemotherapy for his magic bullet approach to medicine – failed and switched to modifying Béchamp's atoxyl, the first organic arsenical drug, and serendipitously obtained a treatment for syphilis – salvarsan – the first successful chemotherapy agent. 
Salvarsan's targeted microorganism, not yet recognized as a bacterium, was still thought to be a parasite, and medical bacteriologists, believing that bacteria were not susceptible to the chemotherapeutic approach, overlooked Alexander Fleming's report in 1928 on the effects of penicillin.

In 1932, Bayer sought medical applications of Aniline dyes. 
Gerhard Domagk identified as an antibacterial a red azo dye, introduced in 1935 as the first antibacterial drug, prontosil, soon found at Pasteur Institute to be a prodrug degraded in vivo into sulfanilamide – a colorless intermediate for many, highly colorfast azo dyes – already with an expired patent, synthesized in 1908 in Vienna by the researcher Paul Gelmo for his doctoral research.
By the 1940s, over 500 related sulfa drugs were produced.

Medications in high demand during World War II (1939–45), these first miracle drugs, chemotherapy of wide effectiveness, propelled the American pharmaceutics industry.
In 1939, at Oxford University, seeking an alternative to sulfa drugs, Howard Florey developed Fleming's penicillin into the first systemic antibiotic drug, penicillin G. (Gramicidin, developed by René Dubos at Rockefeller Institute in 1939, was the first antibiotic, yet Aniline toxicity restricted Aniline to topical use.) 
After World War II, Cornelius P. Rhoads introduced the chemotherapeutic approach to cancer treatment.

Rocket fuel:
Some early American rockets, such as the Aerobee and WAC Corporal, used a mixture of aniline and furfuryl alcohol as a fuel, with nitric acid as an oxidizer. 
The combination is hypergolic, igniting on contact between fuel and oxidizer. 

Aniline is also dense, and can be stored for extended periods. 
Aniline was later replaced by hydrazine.

Human Metabolite Information of Aniline:

Tissue Locations:
Bladder
Epidermis
Prostate
Spleen

Reactivity Profile of Aniline:
Aniline 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. 
Aniline 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.
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.

Handling and Storage of Aniline:

Nonfire Spill Response:
ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area. 
Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. 

Stop leak if you can do Aniline without risk. 
Prevent entry into waterways, sewers, basements or confined areas. 

Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. 
DO NOT GET WATER INSIDE CONTAINERS.

Safe Storage:
Separated from strong oxidants, strong acids and food and feedstuffs. 
Provision to contain effluent from fire extinguishing. 
Store in an area without drain or sewer access.

Storage Conditions:
Keep container tightly closed in a dry and well-ventilated place. 
Containers which are opened must be carefully resealed and kept upright to prevent leakage.

First Aid Measures of Aniline:

Signs and Symptoms of Acute Aniline Exposure: 
Signs and symptoms of acute exposure to aniline may be severe and include dyspnea (shortness of breath), respiratory paralysis, cardiac arrhythmias, and cardiovascular collapse. 
Victims may experience headache, irritability, disorientation, lethargy, weakness, incoordination, dizziness, and drowsiness. 

Delerium, shock, convulsions, and coma may also be observed. 
Gastrointestinal effects include dryness of throat, nausea, and vomiting. 

Painful urination, oliguria (scanty urination), and hematuria (bloody urine) may occur. 
Aniline may irritate the skin, eyes, and mucous membranes; cyanosis (blue tint to skin and mucous membranes) is a common finding. 

Note: 
Victims at special risk include individuals with glucose-6-phosphate-dehydrogenase deficiency, those with liver and kidney disorders, blood diseases, or a history of alcoholism. 

Emergency Life-Support Procedures: 
Acute exposure to aniline may require decontamination and life support for the victims. 
Emergency personnel should wear protective clothing appropriate to the type and degree of contamination. 

Air-purifying or supplied-air respiratory equipment should also be worn, as necessary. 
Rescue vehicles should carry supplies such as plastic sheeting and disposable plastic bags to assist in preventing spread of contamination. 

Inhalation Exposure: 
Move victims to fresh air. 
Emergency personnel should avoid self-exposure to aniline. 

Evaluate vital signs including pulse and respiratory rate, and note any trauma. 
If no pulse is detected, provide CPR. 

If not breathing, provide artificial respiration. 
If breathing is labored, administer oxygen or other respiratory support. 

Obtain authorization and/or further instructions from the local hospital for administration of an antidote or performance of other invasive procedures. 
RUSH to a health care facility. 

Dermal/Eye Exposure: 
Remove victims from exposure. 
Emergency personnel should avoid self- exposure to aniline. 

Evaluate vital signs including pulse and respiratory rate, and note any trauma. 
If no pulse is detected, provide CPR. 

If not breathing, provide artificial respiration. 
If breathing is labored, administer oxygen or other respiratory support. 

Remove contaminated clothing as soon as possible. 
If eye exposure has occurred, eyes must be flushed with lukewarm water for at least 15 minutes. 

Wash exposed skin areas twice with soap and water. 
Obtain authorization and/or further instructions from the local hospital for administration of an antidote or performance of other invasive procedures. 

RUSH to a health care facility. 

Ingestion Exposure: 
Evaluate vital signs including pulse and respiratory rate, and note any trauma. 
If no pulse is detected, provide CPR. 

If not breathing, provide artificial respiration. 
If breathing is labored, administer oxygen or other respiratory support. 

Obtain authorization and/or further instructions from the local hospital for administration of an antidote or performance of other invasive procedures. 
Vomiting may be induced with syrup of Ipecac. 
Ipecac should not be administered to children under 6 months of age.

Warning: 
Ingestion of aniline may result in sudden onset of seizures or loss of consciousness. 
Syrup of Ipecac should be administered only if victims are alert, have an active gag-reflex, and show no signs of impending seizure or coma. 

The following dosages of Ipecac are recommended:
Children up to 1 year old, 10 mL (1/3 oz); children 1 to 12 years old, 15 mL (1/2 oz); adults, 30 mL (1 oz). 
Ambulate (walk) the victims and give large quantities of water. 

If vomiting has not occurred after 15 minutes, Ipecac may be readministered. 
Continue to ambulate and give water to the victims. 
If vomiting has not occurred within 15 minutes after second administration of Ipecac, administer activated charcoal. 

Activated charcoal may be administered if victims are conscious and alert. 
Use 15 to 30 g (1/2 to 1 oz) for children, 50 to 100 g (1-3/4 to 3-1/2 oz) for adults, with 125 to 250 mL (1/2 to 1 cup) of water. 

Promote excretion by administering a saline cathartic or sorbitol to conscious and alert victims. 
Children require 15 to 30 g (1/2 to 1 oz) of cathartic; 50 to 100 g (1-3/4 to 3-1/2 oz) is recommended for adults. 

RUSH to a health care facility.

Fire Fighting of Aniline:
Fight fire from maximum distance. 
Dike fire control water for later disposal and do not scatter material. 

If a leak or spill has not ignited, use water spray to control vapors. 
Wear self-contained breathing apparatus with a full face piece operated in pressure-demand or other positive pressure mode and special protective clothing. 

Use water spray, dry chemical, foam or carbon dioxide. 
Use water to keep fire-exposed containers cool.

Identifiers of Aniline:
CAS Number: 
62-53-3
142-04-1 (HCl)

3DMet: B00082
Beilstein Reference: 605631
ChEBI: CHEBI:17296
ChEMBL: ChEMBL538
ChemSpider: 5889
DrugBank: DB06728
ECHA InfoCard: 100.000.491
EC Number: 200-539-3
Gmelin Reference: 2796
KEGG: C00292

PubChem CID: 
6115
8870 (HCl)

RTECS number: BW6650000

UNII: 
SIR7XX2F1K
576R1193YL (HCl)

UN number: 1547
CompTox Dashboard (EPA): DTXSID8020090

InChI:
InChI=1S/C6H7N/c7-6-4-2-1-3-5-6/h1-5H,7H2
Key: PAYRUJLWNCNPSJ-UHFFFAOYSA-N check
InChI=1/C6H7N/c7-6-4-2-1-3-5-6/h1-5H,7H2
Key: PAYRUJLWNCNPSJ-UHFFFAOYAP

SMILES:
NC1CCCCC1
C1CCC(CC1)N

EC / List no.: 200-539-3
CAS no.: 62-53-3
Mol. formula: C6H7N

CAS number: 62-53-3
EC index number: 612-008-00-7
EC number: 200-539-3
Hill Formula: C₆H₇N
Chemical formula: C₆H₅NH₂
Molar Mass: 93.13 g/mol
HS Code: 2921 41 00

Synonym(s): Aminobenzene, Benzenamine
Linear Formula: C6H5NH2
CAS Number: 62-53-3
Molecular Weight: 93.13
Beilstein: 605631
EC Number: 200-539-3
MDL number: MFCD00007629
eCl@ss: 39030407
PubChem Substance ID: 24854547
NACRES: NA.21

Properties of Aniline:
Chemical formula: C6H7N
Molar mass: 93.129 g·mol−1
Appearance: Colorless liquid
Density: 1.0297 g/mL
Melting point: −6.30 °C (20.66 °F; 266.85 K)
Boiling point: 184.13 °C (363.43 °F; 457.28 K)
Solubility in water: 3.6 g/100 mL at 20 °C
Vapor pressure: 0.6 mmHg (20° C)
Acidity (pKa): 
4.63 (conjugate acid; H2O)
Magnetic susceptibility (χ): −62.95·10−6 cm3/mol
Refractive index (nD): 1.58364
Viscosity: 3.71 cP (3.71 mPa·s at 25 °C)

Boiling point: 184 °C (1013 hPa)
Density: 1.021 g/cm3 (20 °C)
Explosion limit: 1.2 - 11 %(V)
Flash point: 70 °C
Ignition temperature: 540 °C
Melting Point: -6 °C
pH value: 8.8 (36 g/l, H₂O, 20 °C)
Vapor pressure: 0.49 hPa (20 °C)
Solubility: 36 g/l

Grade: ACS reagent
Quality Level: 200
Vapor density: 3.22 (185 °C, vs air)
Vapor pressure: 0.7 mmHg ( 25 °C)
Assay: ≥99.5%
Form: liquid
Autoignition temp.: 1139 °F
Expl. lim.: 11 %

Impurities:
Hydrocarbons, passes test
Nitrobenzene, passes test (lim. ~0.001%)
≤0.01% chlorobenzene

Ign. residue: ≤0.005%
Refractive index: n20/D 1.586 (lit.)
bp: 184 °C (lit.)
mp: −6 °C (lit.)
Solubility: water: soluble
Density: 1.022 g/mL at 25 °C (lit.)
SMILES string: Nc1ccccc1
InChI: 1S/C6H7N/c7-6-4-2-1-3-5-6/h1-5H,7H2
InChI key: PAYRUJLWNCNPSJ-UHFFFAOYSA-N

Molecular Weight: 93.13
XLogP3: 0.9
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 1
Rotatable Bond Count: 0
Exact Mass: 93.057849228
Monoisotopic Mass: 93.057849228
Topological Polar Surface Area: 26 Ų
Heavy Atom Count: 7
Complexity: 46.1
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes

Specifications of Aniline:
Assay (GC, area%): ≥ 99.0 % (a/a)
Density (d 20 °C/ 4 °C): 1.020 - 1.022
Identity (IR): passes test

Appearance: Clear yellow to reddish brown color liquid
Purity (by GC): Min 99.5%
Weight/ mL at 20°C: 1.021-1.023 g
Water (H2O): Max 0.2%
Residue after Ignition: Max 0.005%
Hydrocarbons: Passes test
Nitrobenzene (C6H5NO2): Max 0.003%
Copper (Cu): Max 0.00005%
Iron (Fe): Max 0.0001%
Lead (Pb): Max 0.0001%

Thermochemistry of Aniline:
Std enthalpy of combustion (ΔcH⦵298): −3394 kJ/mol

Names of Aniline:

Preferred IUPAC name:
Aniline

Systematic IUPAC name:
Benzenamine

Other names:
Phenylamine
Aminobenzene
Benzamine
Indigo shrub molecule

Synonyms of Aniline:
ANILINE
Benzenamine
62-53-3
Phenylamine
Aminobenzene
Aminophen
Arylamine
Kyanol
Anilin
Cyanol
Benzeneamine
Benzidam
Krystallin
Anyvim
Anilina
C.I. Oxidation Base 1
Huile D'aniline
Rcra waste number U012
C.I. 76000
Aniline reagent
NCI-C03736
UN 1547
CHEBI:17296
MFCD00007629
SIR7XX2F1K
Benzene, amino
Anilin [Czech]
CI Oxidation Base 1
Caswell No. 051C
Huile d'aniline [French]
HSDB 43
Phenyleneamine
Anilinum
D'aniline
RCRA waste no. U012
Anilina [Italian, Polish]
CCRIS 44
Aniline and homologs
Aniline and homologues
EINECS 200-539-3
UNII-SIR7XX2F1K
UN1547
EPA Pesticide Chemical Code 251400
benzenaminium
cyanole
CI 76000
BIDD:ER0581
phenyl amine
phenyl-amine
AI3-03053
8-aniline
Benzene, amino-
Fentanyl impurity F
2-bromobenzylchloride
Aniline-[13C]
PhNH2
ANILINUM [HPUS]
ANILINE [HSDB]
ANILINE [IARC]
ANILINE [INCI]
ANILINE [MI]
ANILINE [MART.]
ANILINE [USP-RS]
ANILINE [WHO-DD]
CHEMBL538
Epitope ID:117704
EC 200-539-3
Aniline, analytical standard
Aniline, AR, >=99%
Aniline, LR, >=99%
C6H5NH2
Discontinued, see H924510
ANILINE [USP IMPURITY]
DTXSID8020090
BDBM92572
Trimethoprim specified impurity K
Aniline, ReagentPlus(R), 99%
BENZENE,AMINO (ANILINE)
Aniline [UN1547] [Poison]
AMY11081
STR00216
Aniline, ACS reagent, >=99.5%
Tox21_200345
Aniline 10 microg/mL in Cyclohexane
STK301792
ZINC17886255
AKOS000268796
Aniline 100 microg/mL in Cyclohexane
DB06728
Aniline, ASTM, ACS reagent, 99.5%
Aniline, SAJ first grade, >=99.0%
CAS-62-53-3
Aniline, JIS special grade, >=99.0%
Aniline, p.a., ACS reagent, 99.0%
NCGC00091297-01
NCGC00091297-02
NCGC00091297-03
NCGC00257899-01
BP-12047
FENTANYL IMPURITY F [EP IMPURITY]
Aniline, PESTANAL(R), analytical standard
DB-013441
MESALAZINE IMPURITY K [EP IMPURITY]
A0463
FT-0622394
FT-0662220
FT-0696319
TRIMETHOPRIM IMPURITY K [EP IMPURITY]
EN300-33390
C00292
A833829
AMINOBENZOIC ACID IMPURITY C [EP IMPURITY]
Q186414
SR-01000944923
J-519591
SR-01000944923-1
Q27121173
F2190-0417
Aniline, United States Pharmacopeia (USP) Reference Standard
136260-71-4
1-Aminobenzene
224-015-9 [EINECS]
2348-49-4 [RN]
238-580-4 [EINECS]
4-12-00-00223 [Beilstein]
605631 [Beilstein]
62-53-3 [RN]
Aminobenzene [Wiki]
Anilin [German] [ACD/IUPAC Name]
Anilina [Polish]
Aniline [ACD/IUPAC Name] [Wiki]
Aniline [French] [ACD/IUPAC Name]
Benzenamine [ACD/Index Name]
Huile d'aniline [French]
Phenylamidogen
phenylamine
1122-59-4 [RN]
146997-94-6 [RN]
17843-02-6 [RN]
1927175 [Beilstein]
200-539-3MFCD00007629
37342-16-8 [RN]
4-Aminophenyl [ACD/IUPAC Name]
53894-37-4 [RN]
59000-01-0 [RN]
7022-92-6 [RN]
908847-42-7 [RN]
925916-73-0 [RN]
Aminobenzene, Phenylamine, Benzenamine
AMINOPHEN
Anilina
Aniline-d5
ANL
Anyvim
Benzen-d5-amine
Benzene, amino-
Benzidam
Cyanol
Huile D'aniline
Krystallin
kyanol
phenylamino
Phenyleneamine
STR00216