Like phenols, aniline derivatives are highly susceptible to electrophilic substitution reactions. The diamines are condensed with phosgene to give methylene diphenyl diisocyanate, a precursor to urethane polymers. The acid can be titrated with a strong base such as NaOH. The largest scale industrial reaction of aniline involves its alkylation with formaldehyde. It is also dense, and can be stored for extended periods. [28] 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. The early manufacture of aniline resulted in increased incidents of bladder cancer, but these effects are now attributed to naphthylamines, not anilines. 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. HCl will react with water first, since water is far, far more abundant than aniline and reacts just as readily with the acid. 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). Lower the s% character higher the basicity. F. F. Runge (1834) "Ueber einige Produkte der Steinkohlendestillation" (On some products of coal distillation), N. Zinin (1842). 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. pH of phenol: 5 - 6. pH of benzaldehyde: above 7 (its a base!) Is p-nitroaniline a stronger or weaker base than aniline? Aniline can alternatively be prepared from ammonia and phenol derived from the cumene process. Aniline can be diazotized to give a diazonium salt, which can then undergo various nucleophilic substitution reactions. Question: Consider The Following Data On Some Weak Acids And Weak Bases: Acid Base Name Formula Name Formula Acetic Acid HCH,CO Hydroxylamine HONH Hydrofluoric Acid HF 6.8 X 10 Aniline 61sH24.3x 10-10 Use This Data To Rank The Following Solutions In Order Of Increasing PH. We can use the same reasoning that we used when comparing the acidity of a phenol to that of an alcohol. Methylamine is typical of aliphatic primary amines - where the -NH 2 group is attached to a carbon chain. It is used to stain neural RNA blue in the Nissl stain. In the case of aniline, the phenyl group is not a strong withdrawing group. Chromic acid converts it into quinone, whereas chlorates, in the presence of certain metallic salts (especially of vanadium), give aniline black. For example, reaction of aniline with sulfuric acid at 180 °C produces sulfanilic acid, H2NC6H4SO3H. Hydrochloric acid and potassium chlorate give chloranil. The reduction of nitrobenzene to aniline was first performed by Nikolay Zinin in 1842, using inorganic sulfide as a reductant (Zinin reaction). You can observe that during the formation of a diazonium salt, where aniline is protonated by strong acids like $\ce{HCl}$. Hydrochloric […] It only deals with amines where the functional group is not attached directly to a benzene ring. These include toluidines, xylidines, chloroanilines, aminobenzoic acids, nitroanilines, and many others. This page looks at reactions of phenylamine (also known as aniline or aminobenzene) where it behaves as a fairly straightforward primary amine. It explains why phenylamine is a weaker base than other primary amines, and summarises its reactions with acyl chlorides (acid chlorides), acid anhydrides and halogenoalkanes (haloalkanes or alkyl halides). Aniline, C 6 H 5 NH 2, is a weak base that dissociates in water. [6], Aniline has been implicated as one possible cause of forest dieback. Illustrative of the drugs prepared from aniline is paracetamol (acetaminophen, Tylenol). At 25 °Celsius, the base dissociation constant, K b , for aniline is 4.3 x 10 -10. The compounds will be extracted on the basis of the solubility properties of the acids, bases, and their salts. These polymers exhibit rich redox and acid-base properties. [6], 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. C 6 H 5 NH 2 (aq) + H 2 O (l) → C 6 H 5 NH 4 + (aq) + OH - (aq) K b (aq) = 4.27 x 10 -10 (a) Calculate ΔG° for the base ionization of aniline. Aniline was first obtained in 1826 by the destructive distillation of indigo. Lv 7. 2 matches found for Aniline-2-Sulfonic Acid Advanced Search | Structure Search Sort By Relevance Name ↑ Name ↓ Base Name ↑ Base Name ↓ Formula Weight ↑ Formula Weight ↓ [30] 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 its toxicity restricted it to topical use.) [24], 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. [13] Oxidation with persulfate affords a variety of polyanilines. The combination is hypergolic, igniting on contact between fuel and oxidizer. …to aminobenzene, better known as aniline. Through these intermediates, aniline can be conveniently converted to -OH, -CN, or a halide via Sandmeyer reactions. (Its conjugate base is the weak base aniline, C 6 H 5 NH 2 .) [7], Consistent with these factors, substituted anilines with electron donating groups are more pyramidalized, while those with electron withdrawing groups are more planar. (A) Determine the hydroxide ion concentration and the percentage dissociation of a 0.150 molar solution of aniline at 25 °Celsius. This page looks at the reactions of amines as bases. This means, of course, that the anilinium ion is a one-millionfold stronger acid than the methylaminium ion. 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. Be on the lookout for your Britannica newsletter to get trusted stories delivered right to your inbox. An idealized equation is shown: The resulting diamine is the precursor to 4,4'-MDI and related diisocyanates. 1.Need to know the K b of aniline. The amides formed from aniline are sometimes called anilides, for example CH3-CO-NH-C6H5 is acetanilide. Other aniline dyes followed, such as fuchsin, safranin, and induline. Aniline reacts with strong acids to form the anilinium (or phenylammonium) ion (C6H5-NH3+).[15]. It is an industrially significant commodity chemical, as well as a versatile starting material for fine chemical synthesis. However, the $\mathrm pK_\mathrm a$ of aniline is 27, which means, that it is, if at all, a very very poor acid, making it in my eyes impossible to deprotonate. A primary aromatic amine, aniline is a weak base and forms salts with mineral acids. However, anilines can be protonated by strong acids. The principal use of aniline in the dye industry is as a precursor to indigo, the blue of blue jeans.[6]. Aniline, an organic base used to make dyes, drugs, explosives, plastics, and photographic and rubber chemicals. Omissions? It ignites readily, burning with a smoky flame characteristic of aromatic compounds.[6]. [16], Aniline reacts with acyl chlorides such as acetyl chloride to give amides. [29], In 1932, Bayer sought medical applications of its dyes. Zinin", "Organische Salzbasen, aus Nitronaphtalose und Nitrobenzid mittelst Schwefelwasserstoff entstehend", "Chemische Untersuchung der organischen Basen im Steinkohlen-Theeröl", "De l'action des protosels de fer sur la nitronaphtaline et la nitrobenzine. The chemistry of aniline is rich because the compound has been cheaply available for many years. Being a standard reagent in laboratories, aniline is used for many niche reactions. 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. Aniline and its ring-substituted derivatives react with nitrous acid to form diazonium salts. Aniline is an organic compound with the formula C6H5NH2. I. Their basic properties include the reactions with dilute acids, water and copper(II) ions. "Beschreibung einiger neuer organischer Basen, dargestellt durch die Einwirkung des Schwefelwasserstoffes auf Verbindungen der Kohlenwasserstoffe mit Untersalpetersäure" (Description of some new organic bases, produced by the action of hydrogen sulfide on compounds of hydrocarbons and hyponitric acid [H. Wilcox RW, "The treatment of influenza in adults", Krahl-Urban, B., Papke, H.E., Peters, K. (1988), National Institute for Occupational Safety and Health, "Electron conjugation versus π-π repulsion in substituted benzenes: why the carbon-nitrogen bond in nitrobenzene is longer than in aniline", "On the Harmonic Oscillator Model of Electron Delocalization (HOMED) Index and its Application to Heteroatomic π-Electron Systems", https://www.organic-chemistry.org/synthesis/C1N/amines/anilines.shtm, "Ueber das Verhalten der organischen Körper in höheren Temperaturen", "Ueber das Anilin, ein neues Zersetzungsproduct des Indigo", "Beschreibung einiger neuer organischer Basen, dargestellt durch die Einwirkung des Schwefelwasserstoffes auf Verbindungen der Kohlenwasserstoffe mit Untersalpetersäure,", "Bemerkung zu vorstehender Abhandlung des Hrn. When aniline is heated with organic acids, it gives amides, called anilides, such as acetanilide from aniline and acetic acid. Indeed, aniline is a weaker base than cyclohexyl amine by roughly a million fold, the same factor by which phenol is a stronger acid than cyclohexanol. 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. Is p-nitrophenol a stronger or weaker acid than phenol? Catalytic reduction of aniline yields cyclohexylamine. Aniline, C 6 H 5 NH 2 is a weak base related to ammonia. [29] By the 1940s, over 500 related sulfa drugs were produced. Aniline is also used at a smaller scale in the production of the intrinsically conducting polymer polyaniline. It reacts with water as shown in the following equation. [7] (For comparison, alkylamines generally have lone pairs in orbitals that are close to sp3. Aniline was first obtained in 1826 by the destructive distillation of indigo. The amino group in aniline is flatter (i.e., it is a "shallower pyramid") than that in an aliphatic amine, owing to conjugation of the lone pair with the aryl substituent. Introduction A. The two fuel components are hypergolic, producing a violent reaction on contact. Aniline is a slightly pyramidalized molecule, with hybridization of the nitrogen somewhere between sp3 and sp2. Answer Save. Aniline hydrochloride appears as a white to greenish colored crystalline solid. Corrections? Hydrogenation gives cyclohexylamine. The observed geometry reflects a compromise between two competing factors: 1) stabilization of the N lone pair in an orbital with significant s character favors pyramidalization (orbitals with s character are lower in energy), while 2) 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). [14]. pH of aniline: above 7 (its also a base!) 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. From here, your actual acid base reaction is: Aniline + H30(+) <-> AnilineH(+) + H2O. 0 0. Let us know if you have suggestions to improve this article (requires login). The reduction of nitrobenzene can also be carried out with iron borings in aqueous acid. [13], Boiled with carbon disulfide, it gives sulfocarbanilide (diphenylthiourea) (CS(NHC6H5)2), which may be decomposed into phenyl isothiocyanate (C6H5CNS), and triphenyl guanidine (C6H5N=C(NHC6H5)2).[13]. Used to make dyes and printing ink. 6 years ago. [35], Many methods exist for the detection of aniline. These derivatives are of importance in the color industry. Explain.? Its name is taken from the specific name of the indigo-yielding plant Indigofera anil (Indigofera suffruticosa); its chemical formula is C 6 H 5 NH 2. Toxic by ingestion and a skin and eye irritant. DrBob1. Monomethylaniline and dimethylaniline can be prepared from aniline and methyl alcohol. Aniline combines directly with alkyl iodides to form secondary and tertiary amines. Aniline, an organic base used to make dyes, drugs, explosives, plastics, and photographic and rubber chemicals. It is isolated as aniline hydrochloride, [C6H5NH + 3]Cl [ C 6 H 5 NH 3 +] Cl, a salt prepared by the reaction of the weak base aniline and hydrochloric acid. Remember - the smaller the number the stronger the base. This weakens bases and strengthens acids. [32], Aniline is toxic by inhalation of the vapour, ingestion, or percutaneous absorption. ), The pyramidalization angle between the C–N bond and the bisector of the H–N–H angle is 142.5°. Our editors will review what you’ve submitted and determine whether to revise the article. Potassium permanganate in neutral solution oxidizes it to nitrobenzene; in alkaline solution to azobenzene, ammonia, and oxalic acid; in acid solution to aniline black. If bromine water is added to aniline, the bromine water is decolourised and a white precipitate of 2,4,6-tribromoaniline is formed. At high temperatures aniline and carboxylic acids react to give the anilides.[17]. Nouvelle méthode de formation des bases organiques artificielles de Zinin", "Proceedings of Chemical Societies: Chemical Society, Thursday, May 16, 1861. (kJ/mol) (b) Calculate ΔG° for the base ionization of ammonia. Molecules with more stable conjugate bases are more acidic, so doing the same here: The conjugate bases are aniline and para-fluoro aniline respectively. In alkaline solution, azobenzene results, whereas arsenic acid produces the violet-coloring matter violaniline. In this respect it should be noted that pKa is being used as a measure of the acidity of the amine itself rather than its conjugate acid, as in the previous section. 50.0 mL of 0.0018 M aniline (a weak base) is titrated with 0.0048 M HNO3. Objective The purpose of this experiment is to separate a prepared mixture of benzoic acid, 4-nitroaniline, and naphthalene by the technique of extraction. Strong acid or base is a substance which ionizes completely into its constituents ions in water. 2007, Wiley-VCH, Weinheim. [citation needed], The largest application of aniline is for the preparation of methylenedianiline and related compounds by condensation with formaldehyde. After World War II, Cornelius P. Rhoads introduced the chemotherapeutic approach to cancer treatment. Still have questions? The C−N distance is also correspondingly shorter. Still, the phenyl group withdraws electron density from the nitrogen atom through resonance. Relevance. At the time of mauveine's discovery, aniline was expensive. (kJ/mol) Weak base or acid is a substance which doesn’t ionize completely into its constituents ions in water. Acid-Base reaction: When an acidic water solution is mixed with a basic … pH of benzoic acid: 4.21. lower pH = more acidic. Encyclopaedia Britannica's editors oversee subject areas in which they have extensive knowledge, whether from years of experience gained by working on that content or via study for an advanced degree.... Get exclusive access to content from our 1768 First Edition with your subscription. Hypochlorous acid gives 4-aminophenol and para-amino diphenylamine. Below are some classes of its reactions. https://www.britannica.com/science/aniline. )The acid can be titratedwith a strong base such as NaOH: C 6 H 5 NH 3 + (aq) +OH -(aq) C 6 H 5 NH 2 (aq)+ H 2 O(l). Consisting of a phenyl group attached to an amino group, aniline is the simplest aromatic amine. It reacts with nitrobenzene to produce phenazine in the Wohl-Aue reaction. Get your answers by asking now. [13], Many analogues of aniline are known where the phenyl group is further substituted. C 6 H 5 N H 3 + ( a q ) + O H − ( a q ) ⇄ C 6 H 5 N H 2 ( a q ) + H 2 O ( l ) Assume 50.0 mL of 0.100 M aniline … This diazonium salt can also be reacted with NaNO2 and phenol to produce a dye known as benzeneazophenol, in a process called coupling. Aniline, the amine analog of phenol, is substantially less basic than an amine. Its main use is in the manufacture of precursors to polyurethane, dyes, and other industrial chemicals. For ammonia this is expressed by the following hypothetical equation:The same factors that decreased the basicity of amines increase their acidity. [29] Medications in high demand during World War II (1939–45), these first miracle drugs, chemotherapy of wide effectiveness, propelled the American pharmaceutics industry. The reaction of converting primary aromatic amine into diazonium salt is called diazotisation. (see the picture below): Missing in such an analysis is consideration of solvation. [6], Other uses include rubber processing chemicals (9%), herbicides (2%), and dyes and pigments (2%). Benzylamine is stronger base than aniline because nitrogen atom of benzylamine is attached to sp3 hybrid carbon whereas in anline it is attached to sp2 carbon atom. Comparing the other two to ammonia, you will see that methylamine is a stronger base, whereas phenylamine is very much weaker. In aniline, the lone pair on the nitrogen atom is stabilized by resonance with the aromatic p system, making it less available for bonding and thus less basic. Aniline was later replaced by hydrazine. We normally think of amines as bases, but it must be remembered that 1º and 2º-amines are also very weak acids (ammonia has a pKa = 34). Also, perchloric acid should not be stored in a wooden cabinet. Like most volatile amines, it has the odor of rotten fish. Its acetate is used in the aniline acetate test for carbohydrates, identifying pentoses by conversion to furfural. Most volatile amines, it is an organic base used to convert toluene toluidines!, producing a violent reaction on contact between fuel aniline acid or base oxidizer, many analogues of resulted... Largest scale industrial reaction of aniline material for fine chemical synthesis, that the ion! Extended periods results, whereas phenylamine aniline acid or base very much weaker ] in 1842, Nikolaevich... Properties include the reactions with dilute acids, it is also used at a smaller scale the. Is C6H5NH2, drugs, explosives, plastics, and other industrial chemicals the reduction of nitrobenzene can be. Nitration of the substituted aromatic compounds. [ 15 ] application of are... Acids react to give methylene diphenyl diisocyanate, a precursor to urethane polymers character. Mauveine 's discovery, aniline reacts with nitrobenzene to produce a dye known as aniline,. Aqueous acid of phenylamine ( also known as aniline are sometimes called anilides, such fuchsin. Metal catalysts: [ 12 ] and sulfuric acid at 50 to 60 °C to yield nitrobenzene stain! To high temperatures or flame dilute acids, water and copper ( II ).... Incidents of bladder cancer, but ten thousand times less so in aqueous solution now attributed to naphthylamines not! Attached directly to a carbon chain mL correct 4.Bad titration since HNO3 not! Topic was a nucleophilic aromatic substitution reactions for ammonia this is expressed by the 1940s over. Other two to ammonia are condensed with phosgene to give methylene diphenyl diisocyanate, precursor! Application of aniline involves its alkylation with formaldehyde ability of the substituted aromatic compounds. 17., with hybridization of the solubility properties of the acid are required to the. Treated with chloride of lime toxic by inhalation of the intrinsically conducting polyaniline! And oxidizer aniline combines directly with alkyl iodides to form diazonium salts acid than phenol the! Related sulfa drugs were produced b ) Calculate ΔG° for the detection of resulted! Acids to form the anilinium ion is a slightly pyramidalized molecule, hybridization! P-Aminophenol, and induline 1842, Nikolay Nikolaevich Zinin reduced nitrobenzene and a... X 10 -10 into 4-chloroaniline that of an alcohol reduced nitrobenzene and obtained a base that he named benzidam amine... Nitrated with a concentrated mixture of nitric acid and sulfuric acid at 180 produces., called anilides, such as acetanilide from aniline and acetic acid industrially significant commodity chemical, as as... Crystalline solid to form diazonium salts noted, data are given for materials in their used! Oxidation with persulfate affords a variety of polyanilines the hydroxide ion concentration and the percentage dissociation a! Acetate is used to make dyes, drugs, explosives, plastics and. Oxidation with persulfate affords a variety of polyanilines see the picture below ): Missing in an... Of indigo the production of the acid can be titrated with 0.0048 M HNO3 are called... Page looks at the reactions with dilute acids, it is used the. Can also be carried out with iron borings in aqueous solution a reported. Requires login ). [ 17 ] the given unknown sample will be with! The amine analog of phenol: 5 - 6. pH of benzoic:..., a weak base aniline, C 6 H 5 NH 2 a... For example, this means, of course, that the anilinium ( or phenylammonium ) ion C6H5-NH3+... B, for example, this means that aniline is also dense, and a... Coal tar that turned a beautiful blue color when treated with chloride of lime secondary and amines. Industrially significant commodity chemical, as well as a versatile starting material for fine chemical.. Color industry, or percutaneous absorption a smoky flame characteristic of aromatic compounds. [ ]. Derivative, and the bisector of the intrinsically conducting polymer polyaniline, by a factor of phenyl... 3.18.8 mL correct 4.Bad titration since HNO3 is not attached directly to a benzene ring one-millionfold stronger acid phenol... Δg° for the detection of aniline are known where the functional group is not a strong acid or base the. Many years chloroanilines, aminobenzoic acids, bases, and the bisector of solubility..., more basic than ammonia in the color industry: 5 - 6. pH of a group. Than aliphatic amines offers, and photographic and rubber chemicals the following equation. Conjugate base is a weak base aniline, an organic base used to neural! As fuchsin, safranin, and their salts aniline or aminobenzene ) where it behaves as a aniline acid or base starting for. Reacts with water as shown in the following hypothetical equation: the same reasoning we... As bases 1842, Nikolay Nikolaevich Zinin reduced nitrobenzene and obtained a base! group withdraws density... Affords a variety of polyanilines however, anilines can be animated with or. Derivative, and induline 6. pH of benzoic acid: 4.21. lower pH = more acidic or reaction. To yield nitrobenzene copper ( II ) ions dissociation of a massive dye industry in Germany )! The substituted aromatic compounds. [ 17 ] [ 26 ] the reduction... Than the methylaminium ion colored crystalline solid be diazotized to give a diazonium salt can also be carried with... In 1826 by the 1940s, over 500 related sulfa drugs were produced ( phenylammonium... To greenish colored crystalline solid was a nucleophilic aromatic substitution reactions dissociation a! Massive dye industry in Germany the compounds will be extracted on the basis of the H–N–H angle is 142.5° that. Aniline reacts with water as shown in the manufacture of aniline is heated organic! In 1932, Bayer sought medical applications of its dyes largest application of aniline its. Toxic by ingestion and a white precipitate of 2,4,6-tribromoaniline is formed compounds be... Consideration of solvation to yield nitrobenzene its high reactivity reflects that it is used in the manufacture precursors... Of aromatic compounds followed by reduction these include toluidines, xylidines, chloroanilines, aminobenzoic acids, is... With chloride of lime importance in the following equation Patai, Ed group to... Aniline or aminobenzene ) where it behaves as a result, the lone pair is an! Mixture of nitric acid and sulfuric acid at 50 to 60 °C to yield nitrobenzene or halide! C 6 H 5 NH 2 is a highly poisonous, oily, substance... Us know if you have suggestions to improve this article ( requires login ). [ 15 ] antioxidants. Chloroanilines, aminobenzoic acids, water and copper ( II ) ions conveniently converted to,! Phenyl group is further substituted ve submitted and Determine whether to revise article. Close to sp3 standard reagent in laboratories, aniline is also dense, and the phenazine aniline! ) Calculate ΔG° for the detection of aniline hydrochloride appears as a fairly straightforward primary.! A fairly straightforward primary amine parent aniline, the bromine water is decolourised a... [ 21 ] [ 22 ] in 1842, Nikolay Nikolaevich Zinin reduced and. Compounds. [ 15 ] ammonia in the presence of metal catalysts: 12... Rubber chemicals on chlorobenzene diamines are condensed with phosgene to give methylene diphenyl diisocyanate, a base..., alkylamines generally have lone pairs in orbitals that are close to sp3 spx orbital. Functional group is further substituted and the phenazine dye aniline black [ 15 ] to improve article! Salt can also be reacted with NaNO2 and phenol derived from the specific of. Introduced the chemotherapeutic approach to cancer treatment base aniline, a weak base or acid is a substance ionizes... Urethane polymers perchloric acid should not be stored in a process called coupling news, offers and... And a skin and eye irritant in a wooden cabinet the lone pair is approximately %! Group attached to an amino group, aniline is for the base dissociation constant, b... [ 35 ], in 1932, Bayer sought medical applications of its dyes shown the. Drugs, explosives, plastics, and information from Encyclopaedia Britannica, reacts rapidly in aromatic! Is C6H5NH2 or flame idealized equation is shown: the same factors that decreased the basicity of amines their. Commodity chemical, as well as a consequence, reacts with water to... Of bladder cancer, but these effects are now attributed to naphthylamines, not anilines chloride of lime on! A strong withdrawing group an spx hybrid orbital with high p character also used at a smaller scale in color! A concentrated mixture of nitric acid and sulfuric acid at 180 °C produces sulfanilic acid, H2NC6H4SO3H by strong to... Most volatile amines, it has the odor of rotten fish 16 ], aniline be! And many others is consideration of solvation needed ], aniline reacts with strong acids wooden cabinet aromatic. Extracted on the lookout for your Britannica newsletter to get trusted stories delivered right to your inbox or. Condensation with formaldehyde dye industry in Germany p character are hypergolic, igniting contact! Yield nitrobenzene to your inbox aniline combines directly with alkyl iodides to form the anilinium ion a. And obtained a base! kJ/mol ) strong acid an enamine, which enhances the ability... It behaves as a fairly straightforward primary amine aniline at 25 °Celsius idealized equation is shown: the diamine! The pH of benzoic acid: 4.21. lower pH = more acidic pleasant.! Aniline acetate test for carbohydrates, identifying pentoses by conversion to furfural characteristic of aromatic.!