Aniline, phenylamine or aminobenzene (C₆H₅NH₂) is an organic chemical compound which is a primary aromatic amine consisting of a benzene ring and an amino group. The chemical structure of aniline is shown at the right. It is a liquid at room temperature. General Name, Symbol, Number Carbon, C, 6 Chemical series Nonmetals Group, Period, Block 14 (IVA), 2, p Density, Hardness 2267 kg/m3 0. ... General Name, Symbol, Number Hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1 (IA), 1 , s Density, Hardness 0. ... General Name, Symbol, Number Nitrogen, N, 7 Chemical series nonmetals Group, Period, Block 15 (VA), 2 , p Density 1. ... General Name, Symbol, Number Hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1 (IA), 1 , s Density, Hardness 0. ... An organic compound is any of a large class of chemical compounds whose molecules contain carbon, with exception of carbides, carbonates and carbon oxides. ... An aromatic hydrocarbon (abbreviated as AH), or arene is a hydrocarbon, the molecular structure of which incorporates one or more planar sets of six carbon atoms that are connected by delocalised electrons numbering the same as if they consisted of alternating single and double covalent bonds. ... Ammonia Amines are organic compounds containing nitrogen as the key atom in the amine functional group. ... Benzene, C6H6, PhH, or benzol is a colorless and flammable liquid with a pleasant, sweet smell. ... In chemistry, especially in organic chemistry and biochemistry, an amino group is an ammonia-like functional group. ...

Synthesis

Aniline can be produced from benzene in two steps. First, benzene is nitrated (reacted with nitric acid, a form of electrophilic substitution reaction) to give nitrobenzene. Second, the nitrobenzene is reduced to give aniline. A variety of reducing agents are effective for the reduction, including H₂ (with a catalyst), hydrogen sulfide, iron, zinc, or tin. Benzene, C6 H6, PhH, or benzol is a colorless and flammable liquid with a pleasant, sweet smell. ... The chemical compound nitric acid (HNO3), otherwise known as aqua fortis, is a colorless, corrosive liquid, a toxic acid which can cause severe burns. ... Electrophilic substitution reactions are chemical reactions in which an electrophile displaces another group, typically but not always hydrogen. ... Chemical structure of nitrobenzene Nitrobenzene, also known as nitrobenzol or oil of mirbane, is a poisonous organic compound with an almond odor and chemical formula C6H5NO2. ... Reduction or reducing has several meanings: In mathematics, reduction is the process of manipulating a series of equations or matrices into a desired simpler format. ... General Name, Symbol, Number Hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1 (IA), 1 , s Density, Hardness 0. ... For other meaning link to H2S radar. ... General Name, Symbol, Number iron, Fe, 26 Chemical series transition metal Group, Period, Block 8 (VIIIB), 4 , d Density, Hardness 7874 kg/m3, 4. ... General Name, Symbol, Number zinc, Zn, 30 Chemical series transition metals Group, Period, Block 12, 4, d Density, Hardness 7140 kg/m3, 2. ... The word tin is often used to mean a can, even if it does not contain any tin metal. ...

Many derivatives of aniline can be prepared similarly.

Properties

Aniline is a carcinogen. It is oily and although colourless, it can be slowly oxidized and resinified in air to form impurities which can give it a red-brown tint. Its boiling point is 184 °C and its melting point is -6 °C. In pathology, a carcinogen is any substance or agent that promotes cancer. ... Alternate use: Boiling point Boiling Point, known in Japan as 3-4X Jūgatsu (３－４Ｘ１０月 lit. ... link title Headline text Bold textItalic textItalic textInsert non-formatted text hereInsert non-formatted text hereInsert non-formatted text hereInsert non-formatted text hereInsert non-formatted text here--220. ... The melting point of a solid is the temperature at which it changes state from solid to liquid. ...

It ignites readily, burning with a large smoky flame. It possesses a somewhat pleasant vinous odour and a burning aromatic taste; it is a highly acrid poison.

Chemically, aniline is a weak base. Aromatic amines such as aniline are generally much weaker bases than aliphatic amines. Aniline reacts with strong acids to form salts containing the anilinium ion (C₆H₅-NH₃⁺), and reacts with acyl halides (such as acetyl chloride, CH₃COCl) to form amides. The amides formed from aniline are sometimes called anilides, for example CH₃-CO-NH-C₆H₅ is acetanilide. The common (Arrhenius) definition of a base is a chemical compound that either donates hydroxide ions or absorbs hydrogen ions when dissolved in water. ... In chemistry, non-aromatic organic compounds are called aliphatic. ... An acyl halide (also known as an acid halide) is an organic compound containing a carbon atom which is double_bonded to an oxygen atom and singly bonded to a chlorine atom. ... In chemistry, the term amide has several meanings. ...

The sulphate forms beautiful white plates. Although aniline is but feebly basic, it precipitates zinc, aluminium and ferric salts, and on warming expels ammonia from its salts. Aniline combines directly with alkyl iodides to form secondary and tertiary amines; boiled with carbon disulphide it gives sulphocarbanilide (diphenyl thio-urea), CS(NHC₆H₅)₂, which may be decomposed into phenyl mustard-oil, C₆H₅CNS, and triphenyl guanidine, C₆H₅N: C(NHC₆H₅)₂. Sulphuric acid at 180° gives sulphanilic acid, NH₂.C₆H₄.SO₃H. Anilides, compounds in which the amino group is substituted by an acid radical, are prepared by heating aniline with certain acids; antifebrin or acetanilide is thus obtained from acetic acid and aniline. The oxidation of aniline has been carefully investigated. In alkaline solution azobenzene results, while arsenic acid produces the violet-colouring matter violaniline. Chromic acid converts it into quinone, while 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 para-amino phenol and para-amino diphenylamine

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 antibacterials in the early 20th century. Phenols, sometimes called phenolics, are a class of chemical compounds consisting of a hydroxyl functional group (-OH) attached to an aromatic hydrocarbon group. ... Electrophilic substitution reactions are chemical reactions in which an electrophile displaces another group, typically but not always hydrogen. ... Sulfonamides, also known as sulfa drugs, are synthetic antimicrobial agents derived from sulfonic acid. ... Sulfonamides, also known as sulfa drugs, are synthetic antimicrobial agents derived from sulfonic acid. ... An antiseptic is a substance that kills or prevents the growth of bacteria on the external surfaces of the body. ... (19th century - 20th century - 21st century - more centuries) Decades: 1900s 1910s 1920s 1930s 1940s 1950s 1960s 1970s 1980s 1990s As a means of recording the passage of time, the 20th century was that century which lasted from 1901–2000 in the sense of the Gregorian calendar (1900–1999 in the...

Aniline and its ring-substituted derivatives react with nitrous acid to form diazonium ions. Through these, the -NH₂ group of aniline can be conveniently converted to -OH, -CN, or a halide. Nitrous acid weak monobasic acid known only in solution and in the form of nitrite salts. ... The halogens are a chemical series. ...

Uses

The great commercial value of aniline is due to the readiness with which it yields, directly or indirectly, valuable dyestuffs. The discovery of mauve in 1858 by William Perkin was the first of a series of dyestuffs which are now to be numbered by hundreds. Reference should be made to the articles dyeing, fuchsine, safranine, indulines, for more details on this subject. In addition to dyestuffs, it is a starting-product for the manufacture of many drugs, such as antipyrine, antifebrin, etc. Aniline is manufactured by reducing nitrobenzene with iron and hydrochloric acid and steam-distilling the product. The purity of the product depends upon the quality of the benzene from which the nitrobenzene was prepared. 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. Monomethyl and dimethyl aniline are colourless liquids prepared by heating aniline, aniline hydro-chloride and methyl alcohol in an autoclave at 220°. They are of great importance in the colour industry. Monomethyl aniline boils at 193-195°; dimethyl aniline at 192°. A dye can generally be described as a coloured substance that has an affinity to the substrate to which it is being applied. ... 1858 is a common year starting on Friday. ... Sir William Henry Perkin (March 12, 1838 – July 14, 1907) was an English chemist best known for his discovery, at the age of 18, of the first aniline dye, mauveine. ... Dyeing is the process of changing the colour of a yarn or cloth by treatment with a dye. ... Fuchsine or rosaniline hydrochloride is a magenta dye with chemical formula C19H17N3·HCl and CAS number 569-61-9. ...

History

Aniline was first isolated from the destructive distillation of indigo in 1826 by Otto Unverdorben (Pogg. Ann., 1826, 8, p. 397), who named it crystalline. In 1834, F. Runge (Pogg. Ann., 1834, 31, p. 65; 32, p. 331) isolated from coal tar a substance which produced a beautiful blue colour 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 it 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 nīla, dark-blue, and nīlā, the indigo plant. About the same time N. N. Zinin found that on reducing nitrobenzene, a base was formed which he named benzidam. August Wilhelm von Hofmann investigated these variously prepared substances, and proved them to be identical (1855), and thenceforth they took their place as one body, under the name aniline or phenylamine. Indigo dye Indigo dye is an important dyestuff with a distinctive blue color (see indigo). ... Events February 11 - University College London is founded, under the name University of London. ... Events January 1 - Abolition of customs charges at borders within Germany. ... Coal tar is the liquid by-product of the distillation of coal to make coke. ... 1841 is a common year starting on Friday (link will take you to calendar). ... August Wilhelm von Hofmann (April 8, 1818 _ May 5, 1892) was a German chemist. ... 1855 was a common year starting on Monday (see link for calendar). ...

Its first industrial-scale use was in the manufacture of mauveine, a purple dye discovered in 1856 by William Henry Perkin. Mauveine, also known as aniline purple, was the first synthetic organic dye. ... Alternate uses: Purple (disambiguation) Purple is any of a group of colors intermediate between blue and red. ... 1856 was a leap year starting on Tuesday (see link for calendar). ... Sir William Henry Perkin (March 12, 1838 – July 14, 1907) was an English chemist best known for his discovery, at the age of 18, of the first aniline dye, mauveine. ...

This article incorporates text from the public domain 1911 Encyclopædia Britannica. The public domain comprises the body of all creative works and other knowledge—writing, artwork, music, science, inventions, and others—in which no person or organization has any proprietary interest. ... The Eleventh Edition of the Encyclopædia Britannica ( 1911) in many ways represents the sum of knowledge at the beginning of the 20th century. ...