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The two fuel components are hypergolic , producing a violent reaction on contact. Aniline was later replaced by hydrazine. Aniline is toxic by inhalation of the vapour, ingestion, or percutaneous absorption.

The early manufacture of aniline resulted in increased incidents of bladder cancer, but these effects are now attributed to naphthylamines , not anilines.

Aniline has been implicated as one possible cause of forest dieback. Many methods exist for the detection of aniline. From Wikipedia, the free encyclopedia.

Chemical compound. For other uses, see Aniline disambiguation. Aniline [1]. Phenylamine Aminobenzene Benzamine. CAS Number.

Interactive image Interactive image. Beilstein Reference. Gmelin Reference. PubChem CID. Chemical formula. Solubility in water. GHS hazard statements.

GHS precautionary statements. Autoignition temperature. LD Lo lowest published. LC 50 median concentration. LC Lo lowest published.

PEL Permissible. REL Recommended. IDLH Immediate danger. Related aromatic amines. Structure and properties. Spectral data.

Main article: Anilide. Cambridge: The Royal Society of Chemistry. Aniline, for C 6 H 5 -NH 2 , is the only name for a primary amine retained as a preferred IUPAC name for which full substitution is permitted on the ring and the nitrogen atom.

It is a Type 2a retained name; for the rules of substitution see P Substitution is limited to substituent groups cited as prefixes in accordance with the seniority of functional groups explicitly expressed or implied in the functional parent compound name.

The name benzenamine may be used in general nomenclature. CRC Press. Retrieved Lawrence, W. Organic chemistry 7th ed.

Patai, Ed. Professor Chichester, UK. Webb Organic Syntheses. The Chemical Market Reporter. Archived from the original on Annalen der Physik und Chemie.

Bibcode : AnP Runge "Ueber einige Produkte der Steinkohlendestillation" On some products of coal distillation , Annalen der Physik und Chemie , 31 : 65—77 see page 65 , — ; and 32 : — see page Reprinted in: J.

Fritzsche "Ueber das Anilin, ein neues Zersetzungsproduct des Indigo" , Journal für praktische Chemie , 20 : — In a postscript to this article, Erdmann one of the journal's editors argues that aniline and the "cristallin", which was found by Unverdorben in , are the same substance; see pages — Zinin Reprinted in: N.

Zinin "Beschreibung einiger neuer organischer Basen, dargestellt durch die Einwirkung des Schwefelwasserstoffes auf Verbindungen der Kohlenwasserstoffe mit Untersalpetersäure," Journal für praktische Chemie , 27 1 : — Benzidam is named on page Fritzsche, Zinin's colleague, soon recognized that "benzidam" was actually aniline.

See: Fritzsche Bulletin Scientifique , 10 : Reprinted as a postscript to Zinin's article in: J. Fritzsche "Bemerkung zu vorstehender Abhandlung des Hrn.

Zinin" Comment on the preceding article by Mr. Zinin , Journal für praktische Chemie , 27 1 : See also: Anon. On page 48, Hofmann argues that krystallin, kyanol, benzidam, and aniline are identical.

New method of forming Zinin's synthetic organic bases. Note: In the case of a metal having two or more distinct oxides e. See: Wiktionary: protosalt.

Retrieved on Flanagan, S. Brown, F. Braithwaite, B. Widdop: World Health Organization. Namespaces Article Talk. Views Read Edit View history. Help Learn to edit Community portal Recent changes Upload file.

Download as PDF Printable version. Wikimedia Commons. Other names Phenylamine Aminobenzene Benzamine. EC Number. Acidity p K a.

Main hazards. See: data page. Ethnicity: Latino. Body: Athletic. Height: cm. Weight: 55 kg. Hair length: Long. Hair color: Black. Eyes color: Green.

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Like most volatile amines, it has the odor of rotten fish. It ignites readily, burning with a smoky flame characteristic of aromatic compounds.

Aniline is a slightly pyramidalized molecule, with hybridization of the nitrogen somewhere between sp 3 and sp 2.

The amine is flatter than an aliphatic amine, owing to conjugation of the lone pair with the aryl substituent. Thus, the experimental geometry reflects a balance between the stabilization of lone pairs in orbitals with higher s character and better stabilization via conjugation with the aryl ring for an orbital of pure p character.

Industrial aniline production involves two steps. The reduction of nitrobenzene to aniline was first performed by Nikolay Zinin in , using inorganic sulfide as a reductant Zinin reaction.

Aniline can alternatively be prepared from ammonia and phenol derived from the cumene process. 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. The chemistry of aniline is rich because the compound has been cheaply available for many years.

Below are some classes of its reactions. 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 it 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 it 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. These polymers exhibit rich redox and acid-base properties.

Like phenols , aniline derivatives are highly susceptible to electrophilic substitution reactions. Its high reactivity reflects that it is an enamine , which enhances the electron-donating ability of the ring.

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 its alkylation with formaldehyde. An idealized equation is shown:.

The resulting diamine is the precursor to 4,4'-MDI and related diisocyanates. Aniline is a weak base. Aromatic amines such as aniline are, in general, much weaker bases than aliphatic amines.

Traditionally, the weak basicity of aniline is attributed to a combination of inductive effect from the more electronegative sp 2 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 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.

Aniline reacts with acyl chlorides such as acetyl chloride to give amides. At high temperatures aniline and carboxylic acids react to give the anilides.

N -Methylation of aniline with methanol at elevated temperatures over acid catalysts gives N -methylaniline and dimethylaniline :. These derivatives are of importance in the color industry.

Aniline combines directly with alkyl iodides to form secondary and tertiary amines. Aniline and its ring-substituted derivatives react with nitrous acid to form diazonium salts.

Through these intermediates, aniline can be conveniently converted to -OH, -CN, or a halide via Sandmeyer reactions.

This diazonium salt can also be reacted with NaNO 2 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.

It 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. Its acetate is used in the aniline acetate test for carbohydrates, identifying pentoses by conversion to furfural.

It is used to stain neural RNA blue in the Nissl stain. The largest application of aniline is 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.

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 also used at a smaller scale in the production of the intrinsically conducting polymer polyaniline. 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. It is also dense, and can be stored for extended periods.

Aniline was first isolated in by Otto Unverdorben by destructive distillation of indigo. In , Friedlieb Runge isolated a substance from coal tar that turned a beautiful blue color when treated with chloride of lime.

He named it kyanol or cyanol. In , 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.

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. 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.

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 on the effects of penicillin.

In , Bayer sought medical applications of its dyes. Gerhard Domagk identified as an antibacterial a red azo dye, introduced in 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 in Vienna by the researcher Paul Gelmo for his doctoral research.

Rhoads introduced the chemotherapeutic approach to cancer treatment. In the s and early s, aniline was used with nitric acid or dinitrogen tetroxide as rocket fuel for small missiles and the Aerobee rocket.

The two fuel components are hypergolic , producing a violent reaction on contact. Aniline was later replaced by hydrazine. Aniline is toxic by inhalation of the vapour, ingestion, or percutaneous absorption.

The early manufacture of aniline resulted in increased incidents of bladder cancer, but these effects are now attributed to naphthylamines , not anilines.

Aniline has been implicated as one possible cause of forest dieback. Many methods exist for the detection of aniline.

From Wikipedia, the free encyclopedia. Chemical compound. For other uses, see Aniline disambiguation. Aniline [1].

Phenylamine Aminobenzene Benzamine. CAS Number. Body: Athletic. Height: cm. Weight: 55 kg. Hair length: Long. Hair color: Black. Eyes color: Green.

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Analine Analine Explosive limits. Fritzsche "Ueber das Anilin, ein neues Zersetzungsproduct des Indigo"Journal für praktische Chemie20 : — The oxidation of aniline Sissygasm how to been heavily investigated, Pin up fuck can result in reactions localized at nitrogen or more commonly results in the formation of Sophie dee C-N bonds. Its acetate is used in the aniline Analine Polish power ivan putski for carbohydrates, identifying pentoses by conversion to furfural. See also: Anon. Aniline is Family sex xhamster organic compound with the formula C 6 Mature black woman 5 NH 2. The combination is hypergolic2 hot girls on contact between fuel and oxidizer.

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