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Aniline
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62-53-3 Usage

Definition

ChEBI: A primary arylamine in which an amino functional group is substituted for one of the benzene hydrogens.

Purification Methods

Aniline is hygroscopic. It can be dried with KOH or CaH2, and distilled under reduced pressure. Treatment with stannous chloride removes sulfur-containing impurities, reducing the tendency to become coloured by aerial oxidation. It can be crystallised from Et2O at low temperatures. More extensive purifications involve preparation of derivatives, such as the double salt of aniline hydrochloride and cuprous chloride or zinc chloride, or N-acetylaniline (m 114o) which can be recrystallised from water. Redistilled aniline is dropped slowly into a strong aqueous solution ofrecrystallised oxalic acid. Aniline oxalate (m 174-175o) is filtered off, washed several times with water and recrystallised three times from 95% EtOH. Treatment with saturated Na2CO3 solution regenerated aniline which was distilled from the solution, dried and redistilled under reduced pressure [Knowles Ind Eng Chem 12 881 1920]. After refluxing with 10% acetone for 10hours, aniline is acidified with HCl (Congo Red as indicator) and extracted with Et2O until colourless. The hydrochloride is purified by repeated crystallisation before aniline is liberated by addition of alkali, then dried with solid KOH, and distilled. The product is sulfur-free and remains colourless in air [Hantzsch & Freese Chem Ber 27 2529, 2966 1894]. Non-basic materials, including nitro compounds, are removed from aniline in 40% H2SO4 by passing steam through the solution for 1hour. Pellets of KOH are then added to liberate the aniline which is steam distilled, dried with KOH, distilled twice from zinc dust at 20mm, dried with freshly prepared BaO, and finally distilled from BaO in an all-glass apparatus [Few & Smith J Chem Soc 753 1949]. Aniline is absorbed through skin and is TOXIC.[Beilstein 12 IV 223.]

Reactivity Profile

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. Can react vigorously with oxidizing materials (including perchloric acid, fuming nitric acid, sodium peroxide and ozone). Reacts violently with BCl3. Mixtures with toluene diisocyanate may ignite. Undergoes explosive reactions with benzenediazonium-2-carboxylate, dibenzoyl peroxide, fluorine nitrate, nitrosyl perchlorate, peroxodisulfuric acid and tetranitromethane. Violent reactions may occur with peroxyformic acid, diisopropyl peroxydicarbonate, fluorine, trichloronitromethane (293° F), acetic anhydride, chlorosulfonic acid, hexachloromelamine, (HNO3 + N2O4 + H2SO4), (nitrobenzene + glycerin), oleum, (HCHO + HClO4), perchromates, K2O2, beta-propiolactone, AgClO4, Na2O2, H2SO4, trichloromelamine, acids, FO3Cl, diisopropyl peroxy-dicarbonate, n-haloimides and trichloronitromethane. Ignites on contact with sodium peroxide + water. Forms heat or shock sensitive explosive mixtures with anilinium chloride (detonates at 464° F/7.6 bar), nitromethane, hydrogen peroxide, 1-chloro-2,3-epoxypropane and peroxomonosulfuric acid. Reacts with perchloryl fluoride form explosive products. .

Description

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

Incompatibilities

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

Reduction of nitrobenzene with hydrogen

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

Production

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

Uses

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

Chemical Reactivity

Reactivity with Water No reaction; Reactivity with Common Materials: No reaction; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Flush with water and rinse with dilute acetic acid; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.

Derivatives

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

Reaction

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

Chemical Properties

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

Potential Exposure

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

Uses

Aniline is used in the manufacture of dyes,pharmaceuticals, varnishes, resins, photo graphic chemicals, perfumes, shoe blacks,herbicides, and fungicides. It is also usedin vulcanizing rubber and as a solvent. Itoccurs in coal tar and is produced from thedry distillation of indigo. It is also producedfrom the biodegradation of many pesticides.Aniline is a metabolite of many toxic com pounds, such as nitrobenzene, phenacetin,and phenylhydroxylamine.

Industrial uses

Aniline, the simplest primary aromatic amine, consists of a nitrogen atom with two attached hydrogen atoms affixed to a benzene ring. This aromatic amine is a weaker base than the aliphatic amines but aniline does undergo many of the same reactions in the realm of synthetic chemistry. Aniline is used to prepare agricultural chemicals, antioxidants, fungicides, herbicides, isocyanates, and other commercially important chemicals.Aniline is used as a chemical intermediate to prepare isocyanates for making polyurethanes, antioxidants, and vulcanization accelerators, as well as in the manufacture of agricultural fungicides, herbicides and insecticides and in the preparation of certain dyes.

Chemical Properties

Aniline,C6H5NH2, is slightly soluble in water,miscible in alcohol and ether,and turns yellow to brown in air. Aniline may be made(1) by the reduction, with iron or tin in HCI, of nitrobenzene, and(2) by the amination of chlorobenzene by heating with ammonia to a high temperature corresponding to a pressure of over 200 atmospheres in the presence of a catalyst(a mixture of cuprous chlorideandoxide).Aniline is the end point of reduction of most mononitrogen substituted benzene nuclei,as nitro benzene beta-phenyl hydroxylamine, azoxybenzene, azobenzene, hydrazobenzene. Aniline is detected by the violet coloration produced by a small amountof sodium hypochlorite. Aniline is used as a solvent, in the preparation of compound in the manufacture of dyes and their intermediates, and in the manufacture of medicinal chemicals.

Health Hazard

Aniline is a moderate skin irritant, a moderate to severe eye irritant, and a skin sensitizer in animals. Aniline is moderately toxic via inhalation and ingestion. Symptoms of exposure (which may be delayed up to 4 hours) include headache, weakness, dizziness, nausea, difficulty breathing, and unconsciousness. Exposure to aniline results in the formation of methemoglobin and can thus interfere with the ability of the blood to transport oxygen. Effects from exposure at levels near the lethal dose include hypoactivity, tremors, convulsions, liver and kidney effects, and cyanosis. Aniline has not been found to be a carcinogen or reproductive toxin in humans. Some tests in rats demonstrate carcinogenic activity. However, other tests in which mice, guinea pigs, and rabbits were treated by various routes of administration gave negative results. Aniline produced developmental toxicity only at maternally toxic dose levels but did not have a selective toxicity for the fetus. It produces genetic damage in animals and in mammalian cell cultures but not in bacterial cell cultures.

Precautions

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

Hazards

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

General Description

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

Carcinogenicity

The IARC has classified aniline as a Group 3 carcinogen, that is, not classifiable as to its carcinogenicity. However, NIOSH has determined that there is sufficient evidence to recommend that OSHA require labeling this substance a potential occupational carcinogen. This position followed an evaluation of a high-dose feeding study of aniline hydrochloride in F344 rats and B6C3F1 mice (3000 or 6000 ppm and 6000 or 12,000 ppm, respectively). The test was negative in both sexes of mice; however, hemangiosarcomas of the spleen and combined incidence of fibrosarcomas and sarcomas of the spleen were statistically significant in the male rats; the number of female rats having fibrosarcomas of the spleen was also significant.

Environmental fate

Biological. Under anaerobic conditions using a sewage inoculum, 10% of the aniline present degraded to acetanilide and 2-methylquinoline (Hallas and Alexander, 1983). In a 56-d experiment, [14C]aniline applied to soil-water suspensions under aerobic and anaerobic conditions gave 14CO2 yields of 26.5 and 11.9%, respectively (Scheunert et al., 1987). A bacterial culture isolated from the Oconee River in North Georgia degraded aniline to the intermediate catechol (Paris and Wolfe, 1987). Aniline was mineralized by a soil inoculum in 4 d (Alexander and Lustigman, 1966). Soil. A reversible equilibrium is quickly established when aniline covalently bonds with humates in soils forming imine linkages. These quinoidal structures may oxidize to give nitrogensubstituted quinoid rings. The average second-order rate constant for this reaction in a pH 7 buffer at 30 °C is 9.47 x 10-5 L/g?h (Parris, 1980). In sterile soil, aniline partially degraded to azobenzene, phenazine, formanilide, and acetanilide and the tentatively identified compounds nitrobenzene and p-benzoquinone (Pillai et al., 1982). Surface Water. Aniline degraded in pond water containing sewage sludge to catechol, which then degrades to carbon dioxide. Intermediate compounds identified in minor degradative pathways include acetanilide, phenylhydroxylamine, cis,cis-muconic acid, β-ketoadipic acid, levulinic acid, and succinic acid (Lyons et al., 1984). Photolytic. A carbon dioxide yield of 46.5% was achieved when aniline adsorbed on silica gel was irradiated with light (λ >290 nm) for 17 h (Freitag et al., 1985). Products identified from the gas-phase reaction of ozone with aniline in synthetic air at 23 °C were nitrobenzene, formic acid, hydrogen peroxide, and a nitrated salt having the formula: [C6H5NH3]+NO3 - (Atnagel and Himmelreich, 1976). A second-order rate constant of 6.0 x 10-11 cm3/molecule?sec at 26 °C was reported for the vapor-phase reaction of aniline and OH radicals in air at room temperature (Atkinson, 1985). Chemical/Physical. Alkali or alkaline earth metals dissolve in aniline with hydrogen evolution and the formation of anilides (Windholz et al., 1983). Laha and Luthy (1990) investigated the redox reaction between aniline and a synthetic manganese dioxide in aqueous suspensions at the pH range 3.7–6.5. They postulated that aniline undergoes oxidation by loss of one electron forming cation radicals. These radicals may undergo head-to-tail, tail-to-tail, and head-to-head couplings forming 4-aminophenylamine, benzidine, and hydrazobenzene, respectively. These compounds were additionally oxidized, in particular, hydrazobenzene to azobenzene at pH 4 (Laha and Luthy, 1990).

Uses

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

Physical properties

Colorless, oily liquid with a faint ammonia-like odor and burning taste. Gradually becomes yellow to reddish-brown on exposure to air or light. The lower and upper odor thresholds are 2 and 128 ppm, respectively (quoted, Keith and Walters, 1992). An odor threshold of 1.0 ppmv was reported by Leonardos et al. (1969).

Hazard

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

storage

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

Production Methods

Aniline was obtained in 1826 by Unverdorben from distillation of indigo and was given the name aniline in 1841 by Fritzsche (Windholz et al 1983). The chemical was manufactured in the U. S. by the Bechamp reaction involving reduction of nitrobenzene in the presence of either copper/silica or hydrochloric acid/ferrous chloride catalysts; but in 1966, amination of chlorobenzene with ammonia was introduced (IARC 1982; Northcott 1978). Currently, aniline is produced in the U.S., several European countries and Japan by the catalytic hydrogenation of nitrobenzene in either the vapor phase or solvent system. This chemical is also produced by reacting phenol with ammonia (HSDB 1989). Production in 1982 amounted to 331,000 tons (HSDB 1989).

Fire Hazard

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

Shipping

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

Air & Water Reactions

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

Source

Detected in distilled water-soluble fractions of regular gasoline (87 octane) and Gasohol at concentrations of 0.55 and 0.20 mg/L, respectively (Potter, 1996). Aniline was also detected in 82% of 65 gasoline (regular and premium) samples (62 from Switzerland, 3 from Boston, MA). At 25 °C, concentrations ranged from 70 to 16,000 μg/L in gasoline and 20 to 3,800 μg/L in watersoluble fractions. Average concentrations were 5.8 mg/L in gasoline and 1.4 mg/L in watersoluble fractions (Schmidt et al., 2002). Based on laboratory analysis of 7 coal tar samples, aniline concentrations ranged from ND to 13 ppm (EPRI, 1990). Aniline in the environment may originate from the anaerobic biodegradation of nitrobenzene (Razo-Flores et al., 1999).

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 29, p. 1159, 1981 DOI: 10.1248/cpb.29.1159The Journal of Organic Chemistry, 58, p. 5620, 1993 DOI: 10.1021/jo00073a018

Waste Disposal

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

Metabolism

Aniline is absorbed from the skin and the gastrointestinal tract (BaranowskaDutkeiwicz 1982). It is excreted primarily in the urine of treated rabbits with only a small fraction (2%) of the administered dose excreted in the feces (Kao et al 1978; Parke 1960) and none in the expired air. Urinary metabolites of aniline include P-aminophenol, O-aminophenol, m-aminophenol, aniline-N-glucuronide, phenylsulfonic acid and acetanilide (Parke, 1960). Aminophenyl- and acetylaminophenyl-mercapturic acids also have been detected in the urine of rats and rabbits (IARC 1982). Excretion of aniline conjugates of P-aminophenol have been observed in human urine (Williams 1959) and urinary excretion of these conjugates has been found to reflect the extent of absorption of aniline vapor through the skin and respiratory tract (Kao et al 1978; Piotrowski 1972). The methemoglobinemia produced in humans by aniline is believed to result from its N-hydroxylation (IARC 1982). Aniline also is a weak inducer of hepatic microsomal enzymes. Subcutaneous injections of 5 mg/kg body weight for 30 days to rats impaired aniline metabolism in vivo but it increased its in vitro metabolism to p-aminophenol (Wisniewska-Knypl and Jablonska 1975; Wisniewska-Knypl et al 1975). Low protein diets decreased hepatic aniline hydroxylation in the rat (Kato et al 1968). Saturated fat increased aniline metabolism by rat liver independent of chemical composition of the fat used (Caster et al 1970). Highest initial concentrations of aniline derived radioactivity were found in blood, liver, kidney, bladder, and gastrointestinal tract of rat, given labelled compound i.v. After 0.5 h and 6 h, radioactivity concentrated in the stomach and jejunum and subsequently absorbed from the intestine indicating the presence of an enterogastric cycle in rats. Aniline was the predominant compound in the gastric contents of treated animals and acetanilide is the major metabolite found in the jejunal contents (Irons et al 1980).

Flammability and Explosibility

Aniline is a combustible liquid (NFPA rating = 2). Smoke from a fire involving aniline may contain toxic nitrogen oxides and aniline vapor. Toxic aniline vapors are given off at high temperatures and form explosive mixtures in air. Carbon dioxide or dry chemical extinguishers should be used to fight aniline fires.

Uses

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

Safety Profile

Suspected carcinogen with experimental neoplastigenic data. A human poison by an unspecified route. Poison experimentally by most routes incluhng inhalation and ingestion. Experimental reproductive effects. A skin and severe eye irritant, and a rmld sensitizer. In the body, aniline causes formation of methemoglobin, resulting in prolonged anoxemia and depression of the central nervous system; less acute exposure causes hemolysis of the red blood cells, followed by stimulation of the bone marrow. The liver may be affected with resulting jaundice. Long-term exposure to a d n e dye manufacture has been associated with malignant bladder growths. A common air contaminant, A combustible liquid when exposed to heat or flame. To fight fire, use alcohol foam, CO2, dry chemical. It can react vigorously with oxidizing materials. When heated to decomposition it emits highly toxic fumes of NOx. Spontaneously explosive reactions occur with benzenediazonium-2-carboxylate, dibenzoyl peroxide, fluorine nitrate, nitrosyl perchlorate, red fuming nitric acid, peroxodisulfuric acid, and tetranitromethane. Violent reactions with boron trichloride, peroxyformic acid, dhsopropyl peroxydicarbonate, fluorine, trichloronitromethane (145℃), acetic anhydride, chlorosulfonic acid, hexachloromelamine, (HNO3 + N2O4 + H2SO4), (nitrobenzene + glycerin), oleum, (HCHO + HClO4), perchromates, K2O2, ppropiolactone, AgClO4, Na2On, H2SO4, trichloromelamine, acids, peroxydisulfuric acid, F03Cl, diisopropyl peroxy-dicarbonate, n-haloimides, and trichloronitromethane. Ignites on contact with sodium peroxide + water. Forms heator shock-sensitive explosive mixtures with anhnium chloride (detonates at 240°C/7.6 bar), nitromethane, hydrogen peroxide, 1 -chloro-2,3- epoxypropane, and peroxomonosulfuric acid. Reactions with perchloryl fluoride, perchloric acid, and ozone form explosive products.
InChI:InChI=1/C6H7N/c7-6-4-2-1-3-5-6/h1-5H,7H2

62-53-3 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
TCI America (A0463)  Aniline  >98.0%(GC)(T) 62-53-3 500g 255.00CNY Detail
Alfa Aesar (A14443)  Aniline, 99+%    62-53-3 100g 232.0CNY Detail
Alfa Aesar (A14443)  Aniline, 99+%    62-53-3 500g 327.0CNY Detail
Alfa Aesar (A14443)  Aniline, 99+%    62-53-3 1000g 442.0CNY Detail
Alfa Aesar (A14443)  Aniline, 99+%    62-53-3 5000g 1697.0CNY Detail
Alfa Aesar (36238)  Aniline, ACS, 99+%    62-53-3 100ml 229.0CNY Detail
Alfa Aesar (36238)  Aniline, ACS, 99+%    62-53-3 500ml 611.0CNY Detail
Alfa Aesar (36238)  Aniline, ACS, 99+%    62-53-3 1L 1045.0CNY Detail

62-53-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name aniline

1.2 Other means of identification

Product number -
Other names Aniline

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Aniline is predominantly used as a chemical intermediate for the dye, agricultural, polymer, and rubber industries. It is also used as a solvent, and has been used as an antiknock compound for gasolines.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:62-53-3 SDS

62-53-3Synthetic route

bromobenzene
108-86-1

bromobenzene

aniline
62-53-3

aniline

Conditions
ConditionsYield
With copper(I) oxide; ammonium hydroxide In 1-methyl-pyrrolidin-2-one at 80℃; for 15h;100%
With ammonia; copper In water at 100℃; for 24h; Ullmann reaction;99.1%
With copper(l) iodide; 2-carboxyquinoline N-oxide; potassium carbonate; ammonium hydroxide In dimethyl sulfoxide at 80℃; for 23h; Inert atmosphere;98%
nitrobenzene
98-95-3

nitrobenzene

aniline
62-53-3

aniline

Conditions
ConditionsYield
With hydrogen; platinum In water at 20℃; Product distribution; other temp.;100%
With ethanol; water; tetrabutylammonium hypophosphite; benzene; palladium on activated charcoal for 5h; Product distribution; Heating; hydrogenation in a biphasic solvent system;100%
With hydrogen; Pd in AV-17-8-Pd In ethanol at 40℃; under 760 Torr; Rate constant;100%
nitrobenzene
98-95-3

nitrobenzene

A

aniline
62-53-3

aniline

B

diphenyl hydrazine
122-66-7

diphenyl hydrazine

Conditions
ConditionsYield
With ammonia borane; gold on titanium oxide In ethanol at 20℃; for 0.5h; Inert atmosphere;A 92%
B 100%
With samarium; iodine; ammonium chloride In tetrahydrofuran; water at 20℃; for 4h; Reduction;A 56%
B 20%
Electrolysis;
Nitrosobenzene
586-96-9

Nitrosobenzene

aniline
62-53-3

aniline

Conditions
ConditionsYield
With hydrazine hydrate In ethanol; water at 80℃; chemoselective reaction;100%
With ammonium hydroxide; nickel boride at 40℃; for 0.5h; Product distribution; further medium: 3N HCl;94.4%
With copper(I) chloride; potassium borohydride In methanol for 0.416667h; Product distribution; Ambient temperature; reduction of aromatic nitro compounds, nitrozobenzene, azobenzene and azoxybenzene with potassium borohydride-copper(I) chloride to primary amines;94%
Phenyl azide
622-37-7

Phenyl azide

aniline
62-53-3

aniline

Conditions
ConditionsYield
With sodium hydrogen telluride In diethyl ether; ethanol for 0.25h; Ambient temperature;100%
With iron(III)-acetylacetonate; hydrazine hydrate In methanol at 150℃; for 0.05h; Microwave irradiation; chemoselective reaction;99%
With dibutyltin In benzene at 15℃; for 5h; other reagents;98%
benzene
71-43-2

benzene

aniline
62-53-3

aniline

Conditions
ConditionsYield
With tris-(2-chloro-ethyl)-amine; trifluorormethanesulfonic acid; trifluoroacetic acid In chloroform at 40℃; for 12h; Product distribution; Mechanism; various acids, various substrates;100%
With trifluorormethanesulfonic acid; trimethylsilylazide at 55℃; for 0.833333h; Product distribution; Mechanism; other arenes or substituted arenes; var. temperatures and time;95%
With trifluorormethanesulfonic acid; trimethylsilylazide In chloroform at 90℃; under 5250.53 Torr; for 0.0466667h; Flow reactor;86%
carbamic acid, phenyl-, 1-methylethyl ester
122-42-9

carbamic acid, phenyl-, 1-methylethyl ester

aniline
62-53-3

aniline

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water at 100℃; for 0.666667h; Product distribution;100%
3-(4-nitro-phenoxy)-benz[d]isothiazole-1,1-dioxide
132636-65-8

3-(4-nitro-phenoxy)-benz[d]isothiazole-1,1-dioxide

A

aniline
62-53-3

aniline

B

saccharin
81-07-2

saccharin

Conditions
ConditionsYield
With sodium hypophosphite; palladium on activated charcoal In water; benzene for 0.25h; Heating;A 100%
B n/a
benzamide
55-21-0

benzamide

aniline
62-53-3

aniline

Conditions
ConditionsYield
With sodium hypochlorite; sodium hydroxide In 1,4-dioxane; water at 80℃; for 0.25h; Hofmann degradation;100%
With sodium hydroxide; benzyltrimethylazanium tribroman-2-uide In water for 2h; Ambient temperature;72%
With water; bromine; sodium hydroxide Hofmann Rearrangement; Cooling with ice;
N-Phenylhydroxylamine
100-65-2

N-Phenylhydroxylamine

aniline
62-53-3

aniline

Conditions
ConditionsYield
With hydrazine hydrate In ethanol; water at 80℃; chemoselective reaction;100%
With sodium tetrahydroborate; meso-tetraphenylporphyrin iron(III) chloride In methanol; diethylene glycol dimethyl ether at 25℃; for 3h; Product distribution; Further Variations:; Reagents;98%
With hydrogen In ethanol at 30℃; under 1875.19 Torr; for 1h; Irradiation; Autoclave;95%
isobutyric acid-(N'-phenyl-hydrazide)
5461-50-7

isobutyric acid-(N'-phenyl-hydrazide)

A

ISOPROPYLAMIDE
563-83-7

ISOPROPYLAMIDE

B

aniline
62-53-3

aniline

Conditions
ConditionsYield
With hydrogen; palladium In ethanol; acetic acid under 2585.7 Torr;A 100%
B n/a
As,As-bis(p-bromophenyl)-N,N'-diphenylarsinimidic amide

As,As-bis(p-bromophenyl)-N,N'-diphenylarsinimidic amide

A

bis(p-bromophenyl)arsinic acid
113827-90-0

bis(p-bromophenyl)arsinic acid

B

aniline
62-53-3

aniline

Conditions
ConditionsYield
With water In diethyl etherA 100%
B n/a
t-butyl N-phenyl sulfinamoyl acetate
82185-52-2

t-butyl N-phenyl sulfinamoyl acetate

benzylamine
100-46-9

benzylamine

A

Benzylamino-thioxo-acetic acid tert-butyl ester
130293-09-3

Benzylamino-thioxo-acetic acid tert-butyl ester

B

aniline
62-53-3

aniline

Conditions
ConditionsYield
In diethyl ether for 72h; Ambient temperature;A 63%
B 100%
In diethyl ether for 72h; Mechanism; Ambient temperature; reaction of other substituted t-butyl sulfinamoyl acetates;A 63%
B 100%
azoxybenzene
495-48-7

azoxybenzene

aniline
62-53-3

aniline

Conditions
ConditionsYield
With copper(I) chloride; potassium borohydride In methanol for 0.25h; Product distribution; Ambient temperature; reduction of aromatic nitro compounds , nitrosobenzene, azobenzene and azoxybenzene with potassium borohydride-copper(I) chloride to primary amines;100%
With N-doped TiO2 In methanol at 20℃; for 3h; UV-irradiation; Inert atmosphere;92%
With 4,4'-di-tert-butylbiphenyl; lithium; nickel dichloride In tetrahydrofuran at 20℃; for 10h; Reduction; deoxygenation;66%
(HRu3(CO)9((C6H5)N))(1-)

(HRu3(CO)9((C6H5)N))(1-)

carbon monoxide
201230-82-2

carbon monoxide

aniline
62-53-3

aniline

Conditions
ConditionsYield
With H2 In not given Ru compound heated at 80°C under CO-H2 (1:1);100%
(((C6H5)3P)2N)(1+)*(HRu3(CO)9((C6H5)NCO))(1-)=(((C6H5)3P)2N)(HRu3(CO)9((C6H5)NCO))

(((C6H5)3P)2N)(1+)*(HRu3(CO)9((C6H5)NCO))(1-)=(((C6H5)3P)2N)(HRu3(CO)9((C6H5)NCO))

carbon monoxide
201230-82-2

carbon monoxide

aniline
62-53-3

aniline

Conditions
ConditionsYield
With H2 In not given Ru compound heated at 80°C under CO-H2 (1:1);100%
iodobenzene
591-50-4

iodobenzene

aniline
62-53-3

aniline

Conditions
ConditionsYield
With iron(III) oxide; sodium hydroxide; copper(l) iodide; ammonia In ethanol; water at 90℃; for 16h;100%
With copper(I) oxide; ammonium hydroxide In 1-methyl-pyrrolidin-2-one at 80℃; for 15h;99%
With ammonia; triethylamine In water at 20℃; for 2.5h; Reagent/catalyst; Solvent; Time;98%
anilino(tert-butyldimethyl)silane
53742-62-4

anilino(tert-butyldimethyl)silane

aniline
62-53-3

aniline

Conditions
ConditionsYield
With silica gel In ethanol; water at 20℃; for 2h;100%
2-methyl-1,2,3,4-tetrahydroquinolin-4-yl-(phenyl)amine
1026-05-7

2-methyl-1,2,3,4-tetrahydroquinolin-4-yl-(phenyl)amine

A

2-methylquinoline
91-63-4

2-methylquinoline

B

aniline
62-53-3

aniline

Conditions
ConditionsYield
With palladium dichloride In acetonitrileA 100%
B 100%
4-chloro-aniline
106-47-8

4-chloro-aniline

aniline
62-53-3

aniline

Conditions
ConditionsYield
With ammonium formate In water; isopropyl alcohol at 20℃; for 3h;99%
With hydrogen; triethylamine In water at 120 - 140℃; under 22502.3 - 37503.8 Torr;99%
With hydrogen; NiCl2-Li-[poly(2-vinyl-naphthalene)-co-(divinylbenzene)] In tetrahydrofuran at 20℃; under 760.051 Torr; for 2h;98%
3-chloro-aniline
108-42-9

3-chloro-aniline

aniline
62-53-3

aniline

Conditions
ConditionsYield
With hydrogen; triethylamine In water at 120 - 140℃; under 22502.3 - 37503.8 Torr;99%
With lithium at 230℃; Zersetzen der Reaktionsprodukte mit Wasser;
With potassium fluoride; polymethylhydrosiloxane; palladium diacetate In tetrahydrofuran at 20℃; for 0.75h;94 % Spectr.
4-chlorobenzonitrile
100-00-5

4-chlorobenzonitrile

aniline
62-53-3

aniline

Conditions
ConditionsYield
With ammonium formate In water at 20℃; for 3h;99%
With ammonium formate; PdMCM-41 In methanol at 69.84℃; for 0.666667h;95%
With palladium on activated charcoal; formic acid; N,N-dimethyl-formamide for 3h; Heating;90%
4-bromo-aniline
106-40-1

4-bromo-aniline

aniline
62-53-3

aniline

Conditions
ConditionsYield
With hydrogen; triethylamine In water at 120 - 140℃; under 22502.3 - 37503.8 Torr; Temperature;99%
With methanol; gold; hydrogen; caesium carbonate at 100℃; under 3800.26 Torr; for 155h;80%
Stage #1: 4-bromo-aniline With palladium dichloride In water at 20℃; for 0.0333333h;
Stage #2: With 1,1,3,3-Tetramethyldisiloxane for 0.383333h;
79%
tert-butyl phenylcarbamate
3422-01-3

tert-butyl phenylcarbamate

aniline
62-53-3

aniline

Conditions
ConditionsYield
With water at 100℃; for 10h; Inert atmosphere;99%
HY-Zeolite In dichloromethane for 1.5h; Heating;92%
With 3-butyl-l-methyl-1H-imidazol-3-iumtrifloroacetate In 1,4-dioxane; water at 70 - 72℃; for 1h;92%
styrene
292638-84-7

styrene

nitrobenzene
98-95-3

nitrobenzene

A

ethylbenzene
100-41-4

ethylbenzene

B

aniline
62-53-3

aniline

Conditions
ConditionsYield
With hydrogen; 5% rhodium-on-charcoal; tris(acetylacetonato)cobalt In tetrahydrofuran at 20℃; for 16h;A 99%
B 89%
With hydrogen; 5% rhodium-on-charcoal; iron(II) acetate In tetrahydrofuran at 20℃; for 16h;A 98%
B 80%
With hydrogen; 5% rhodium-on-charcoal In tetrahydrofuran at 20℃; for 16h; Product distribution / selectivity;A 93%
B 31%
With hydrogen at 110℃; under 4560.31 Torr; for 24h; Autoclave; chemoselective reaction;
4-nitrobenzanilide
3460-11-5

4-nitrobenzanilide

A

aniline
62-53-3

aniline

B

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

Conditions
ConditionsYield
With 40% potassium fluoride/alumina for 0.0666667h; Microwave irradiation; Neat (no solvent);A 90%
B 99%
3,5-Dichloroaniline
626-43-7

3,5-Dichloroaniline

aniline
62-53-3

aniline

Conditions
ConditionsYield
With ammonium formate In water; isopropyl alcohol at 20℃; for 3h;99%
With Raney aluminium-nickel alloy; water; sodium hydroxide In dimethoxymethane at 25℃; for 17h;
2,4-Dichloroaniline
554-00-7

2,4-Dichloroaniline

aniline
62-53-3

aniline

Conditions
ConditionsYield
With ammonium formate In water; isopropyl alcohol at 20℃; for 3h;99%
With methylene blue; sodium hydroxide Kinetics; Concentration; pH-value; Temperature; Irradiation;
nitrobenzene
98-95-3

nitrobenzene

12percent nickel/Al-SBA-15 fiber

12percent nickel/Al-SBA-15 fiber

aniline
62-53-3

aniline

Conditions
ConditionsYield
With hydrogen In ethanol at 109.84℃; under 18751.9 Torr; for 7.5h; Autoclave; Green chemistry; chemoselective reaction;99%
Cyclopentene oxide
285-67-6

Cyclopentene oxide

aniline
62-53-3

aniline

trans-2-(phenylamino)cyclopentanol
77924-49-3, 101593-89-9

trans-2-(phenylamino)cyclopentanol

Conditions
ConditionsYield
With zirconium(IV) chloride at 20℃; for 0.25h;100%
With lithium bromide at 20℃; for 5h;100%
With sulfated zirconia In neat (no solvent) at 20℃; for 0.5h; regioselective reaction;98%
furfural
98-01-1

furfural

aniline
62-53-3

aniline

N-(2-furylmethylene)aniline
3237-23-8

N-(2-furylmethylene)aniline

Conditions
ConditionsYield
With copper(II) bis(trifluoromethanesulfonate) In water at 20℃; for 0.0166667h;100%
With aluminum oxide for 5h; Milling;100%
sodium hydrogen sulfate; silica gel at 56 - 58℃; for 0.0244444h; microwave irradiation;98%
maleic anhydride
108-31-6

maleic anhydride

aniline
62-53-3

aniline

N-phenylmaleamic acid
555-59-9, 4437-08-5, 37902-58-2

N-phenylmaleamic acid

Conditions
ConditionsYield
In diethyl ether Ring cleavage; Substitution;100%
In dichloromethane at 20℃; for 1h;100%
at 20℃; for 2h;99%
phthalic anhydride
85-44-9

phthalic anhydride

aniline
62-53-3

aniline

N-phenylphthalimide
520-03-6

N-phenylphthalimide

Conditions
ConditionsYield
Stage #1: phthalic anhydride; aniline In N,N-dimethyl acetamide at 20℃; for 24h;
Stage #2: In N,N-dimethyl acetamide; xylene at 140℃; for 48h;
100%
In 1,2-dichloro-benzene at 180 - 190℃; for 5h; Dean-Stark;100%
In 1,2-dichloro-benzene at 180 - 190℃; for 5h; Dean-Stark;100%
Phenyl glycidyl ether
122-60-1

Phenyl glycidyl ether

aniline
62-53-3

aniline

N-(2-hydroxy-3-phenoxypropyl)aniline
16112-55-3, 113279-34-8

N-(2-hydroxy-3-phenoxypropyl)aniline

Conditions
ConditionsYield
With zirconium(IV) chloride at 20℃; for 0.25h;100%
With lithium bromide at 20℃; for 5h;100%
silica gel at 20℃; for 3h;100%
cyclohexane-1,2-epoxide
286-20-4

cyclohexane-1,2-epoxide

aniline
62-53-3

aniline

Conditions
ConditionsYield
In water at 60℃; for 18h;100%
With acetic acid at 20 - 25℃; for 1h; Temperature; Reagent/catalyst;100%
With PhCNAl(OC(CF3)2PhCH3)3 at 25℃; for 4h; Inert atmosphere; Neat (no solvent);99%
cyclohexane-1,2-epoxide
286-20-4

cyclohexane-1,2-epoxide

aniline
62-53-3

aniline

Conditions
ConditionsYield
With bis(trifluoromethane)sulfonimide lithium at 20℃; for 20h; without solvent;100%
With zirconium(IV) chloride at 20℃; for 0.25h;100%
Montmorillonite K 10 at 20℃; for 3h; Product distribution; Further Variations:; Catalysts; reaction times;100%
acetic anhydride
108-24-7

acetic anhydride

aniline
62-53-3

aniline

Acetanilid
103-84-4

Acetanilid

Conditions
ConditionsYield
With pyridine; aluminum oxide at 93 - 95℃; for 1h; microwave irradiation;100%
In dichloromethane at 20℃; Inert atmosphere;100%
In dichloromethane at 21℃; Inert atmosphere;100%
4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

aniline
62-53-3

aniline

N-(4-chlorobenzylidene)aniline
2362-79-0

N-(4-chlorobenzylidene)aniline

Conditions
ConditionsYield
With acetic acid In 1,2-dichloro-ethane at 20℃; for 24h; Inert atmosphere;100%
With formic acid In ethanol; water at 20℃; for 0.0166667h; Green chemistry;99%
at 20℃; for 14h; Molecular sieve;98%
cinnamoyl chloride
102-92-1

cinnamoyl chloride

aniline
62-53-3

aniline

Conditions
ConditionsYield
With pyridine In toluene for 12h;100%
With triethylamine In dichloromethane at 20℃; Inert atmosphere;100%
With triethylamine In ethyl acetate at 0 - 20℃;94%
1-naphthaldehyde
66-77-3

1-naphthaldehyde

aniline
62-53-3

aniline

[1]naphthylmethylen-aniline
890-50-6

[1]naphthylmethylen-aniline

Conditions
ConditionsYield
In chloroform Ambient temperature;100%
In benzene Heating;74%
In water at 20℃; for 2h;69%
2-ethoxycarbonyl-1-cyclopentanone
611-10-9

2-ethoxycarbonyl-1-cyclopentanone

aniline
62-53-3

aniline

2-(N-phenylcarbamoyl)cyclopentanone
4874-65-1

2-(N-phenylcarbamoyl)cyclopentanone

Conditions
ConditionsYield
In neat (no solvent) at 180℃; for 0.75h; Microwave irradiation; Green chemistry;100%
In 5,5-dimethyl-1,3-cyclohexadiene at 160℃; Inert atmosphere;90%
With dmap In toluene for 9.5h; Reflux; Inert atmosphere;39%
3,4,5-trimethoxy-benzaldehyde
86-81-7

3,4,5-trimethoxy-benzaldehyde

aniline
62-53-3

aniline

N-(3,4,5-trimethoxybenzylidene)aniline
114468-30-3, 32349-41-0

N-(3,4,5-trimethoxybenzylidene)aniline

Conditions
ConditionsYield
In chloroform Ambient temperature;100%
sodium hydrogen sulfate; silica gel at 60 - 62℃; for 0.025h; microwave irradiation;94%
In ethanol at 20℃;87%
trityl chloride
76-83-5

trityl chloride

aniline
62-53-3

aniline

Phenyl-trityl-amine
4471-22-1

Phenyl-trityl-amine

Conditions
ConditionsYield
Stage #1: trityl chloride; aniline at 190℃; for 0.5h;
Stage #2: With hydrogenchloride In methanol for 0.5h; Reflux;
100%
at 50℃; for 1.5h;63%
With pyridine at 20℃; for 24h; Substitution;44%
benzaldehyde
100-52-7

benzaldehyde

aniline
62-53-3

aniline

N-Benzylaniline
758640-21-0

N-Benzylaniline

Conditions
ConditionsYield
With tri-n-butyl-tin hydride; silica gel at 20℃; for 1h;100%
With sodium tetrahydroborate; triethylamine In methanol100%
With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 18℃; for 1h; Solvent; Reagent/catalyst; Green chemistry;100%
benzaldehyde
100-52-7

benzaldehyde

aniline
62-53-3

aniline

benzylidene phenylamine
538-51-2

benzylidene phenylamine

Conditions
ConditionsYield
In chloroform Ambient temperature;100%
In toluene at 120℃; for 24h;100%
With alumina-entrapped Ag at 120℃; under 750.075 Torr; for 1h; Inert atmosphere; Autoclave;100%
benzaldehyde
100-52-7

benzaldehyde

aniline
62-53-3

aniline

Conditions
ConditionsYield
In ethanol for 6h; Reflux;100%
In toluene Inert atmosphere; Schlenk technique; Molecular sieve;100%
With silica gel In ethanol at 20℃; Ultrasound irradiation;99%
4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

aniline
62-53-3

aniline

p-methoxybenzylidene-phenylamine
836-41-9

p-methoxybenzylidene-phenylamine

Conditions
ConditionsYield
In chloroform Ambient temperature;100%
In toluene for 1h; Ambient temperature;100%
In benzene for 4h; Reflux; Dean-Stark;100%
salicylaldehyde
90-02-8

salicylaldehyde

aniline
62-53-3

aniline

N-phenylsalicylaldimine
779-84-0

N-phenylsalicylaldimine

Conditions
ConditionsYield
at 50℃; for 4h;100%
With sodium sulfate In dichloromethane for 4h; Reflux;100%
In methanol at 20℃; for 1h;98%
benzoyl chloride
98-88-4

benzoyl chloride

aniline
62-53-3

aniline

N-phenyl benzoyl amide
93-98-1

N-phenyl benzoyl amide

Conditions
ConditionsYield
With pyridine; aluminum oxide at 92 - 94℃; for 0.0166667h; microwave irradiation;100%
With triethylamine In dichloromethane at 0 - 20℃; for 16h; Inert atmosphere;100%
With triethylamine In tetrahydrofuran at 0 - 20℃; for 2.5h; Inert atmosphere; Schlenk technique; Glovebox;99.5%
phenyl isocyanate
103-71-9

phenyl isocyanate

aniline
62-53-3

aniline

bis(diphenyl)urea
102-07-8

bis(diphenyl)urea

Conditions
ConditionsYield
With triethylamine In dichloromethane100%
In acetic acid for 0.0833333h;98%
In hexane95%
vanillin
121-33-5

vanillin

aniline
62-53-3

aniline

N-(4-hydroxy-3-methoxybenzylidene)aniline
17696-53-6

N-(4-hydroxy-3-methoxybenzylidene)aniline

Conditions
ConditionsYield
With aluminum oxide for 5h; Milling;100%
sodium hydrogen sulfate; silica gel at 58 - 60℃; for 0.0208333h; microwave irradiation;96%
With aqueous extract of pericarp of Sapindus trifoliatus fruits at 20℃; for 0.333333h;93%
4-nitro-benzoyl chloride
122-04-3

4-nitro-benzoyl chloride

aniline
62-53-3

aniline

4-nitrobenzanilide
3460-11-5

4-nitrobenzanilide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 2.5h;100%
With pyridine Reflux;95%
With pyridine at 20℃; Inert atmosphere; Reflux;91%
3,4-dimethoxy-benzaldehyde
120-14-9

3,4-dimethoxy-benzaldehyde

aniline
62-53-3

aniline

N-(3,4-dimethoxybenzylidene)aniline
27895-67-6

N-(3,4-dimethoxybenzylidene)aniline

Conditions
ConditionsYield
In toluene Heating;100%
sodium hydrogen sulfate; silica gel at 56 - 58℃; for 0.0222222h; microwave irradiation;95%
magnesium(II) perchlorate In 1,2-dichloro-ethane at 20℃; for 4h;94%
Conditions
ConditionsYield
With iron(III) chloride hexahydrate In toluene for 6.5h; Solvent; Reagent/catalyst; Reflux;100%
at 20 - 120℃; for 15h;99%
at 120℃; for 15h;99%
acetic acid
64-19-7

acetic acid

aniline
62-53-3

aniline

Acetanilid
103-84-4

Acetanilid

Conditions
ConditionsYield
With dmap; 2-chloro-1-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,12-henicosafluorododecyl)pyridinium trifluoromethanesulfonate; triethylamine In N,N-dimethyl-formamide at 20℃; for 1h;100%
With dmap; 2-chloro-1-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,12-henicosafluorododecyl)pyridinium trifluoromethanesulfonate; triethylamine In N,N-dimethyl-formamide at 20℃; for 1h;100%
With zinc(II) oxide for 2.33h; Reflux; chemoselective reaction;99%
methyl vinyl ketone
78-94-4

methyl vinyl ketone

aniline
62-53-3

aniline

4-phenylamino-butan-2-one
6220-79-7

4-phenylamino-butan-2-one

Conditions
ConditionsYield
In water at 20℃; for 24h; Michael condensation;100%
With Nafion(R) SAC-13 In acetonitrile at 20℃; for 12h;98%
With bis(trifluoromethanesulfonyl)amide In acetonitrile for 4h; Michael addition;98%
chloroacetonitrile
107-14-2

chloroacetonitrile

aniline
62-53-3

aniline

N-phenylglycinonitrile
3009-97-0

N-phenylglycinonitrile

Conditions
ConditionsYield
With potassium carbonate; sodium iodide In acetonitrile for 3h; Reflux;100%
With potassium carbonate; sodium iodide In acetonitrile for 3h; Reflux;100%
With triethylamine In ethanol for 4h; Heating;22%
butyraldehyde
123-72-8

butyraldehyde

aniline
62-53-3

aniline

N-(n-butyl)aniline
1126-78-9

N-(n-butyl)aniline

Conditions
ConditionsYield
With ammonium formate; palladium on activated charcoal In water; isopropyl alcohol at 20℃; for 0.5h;100%
With 1.1 wt% Pd/NiO; hydrogen In ethanol at 25℃; under 760.051 Torr; for 10h;98%
With sodium tetrahydroborate In tetrahydrofuran at 20℃;96%
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