Aniline

Base Information

• Chemical Name: Aniline
• CAS No.: 62-53-3
• Deprecated CAS: 146997-94-6,37342-16-8,1533423-51-6,1582784-51-7,1619933-02-6,37342-16-8
• Molecular Formula: C6H7N
• Molecular Weight: 93.1283
• Hs Code.: 2921 41 00
• European Community (EC) Number: 200-539-3,294-999-2,308-052-9,686-085-0
• ICSC Number: 0011
• UN Number: 1547
• UNII: SIR7XX2F1K
• DSSTox Substance ID: DTXSID8020090
• Nikkaji Number: J2.349C
• Wikipedia: Aniline
• Wikidata: Q186414,Q27121173,Q83081722
• Metabolomics Workbench ID: 38235
• ChEMBL ID: CHEMBL538
• Mol file: 62-53-3.mol

Synonyms:Phenylamine;Arylamine;Aminophen;Benzene, amino;Kyanol;Anilinium nitrate;Phenyleneamine;Anyvim;Aniline and homologues;Aniline oil;Benzidam;Aniline, Reagent;

Chemical Property of Aniline

Chemical Property:

• Appearance/Colour: colourless liquid
• Vapor Pressure: 0.7 mm Hg ( 25 °C)
• Melting Point: -6.2 °C
• Refractive Index: n20/D 1.586(lit.)
• Boiling Point: 184.449 °C at 760 mmHg
• PKA: 4.63(at 25℃)
• Flash Point: 70 °C
• PSA: 26.02000
• Density: 1.015 g/cm³
• LogP: 1.85000
• Storage Temp.: 2-8°C
• Solubility.: water: soluble
• Water Solubility.: 36 g/L (20 ºC)
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 93.057849228
• Heavy Atom Count: 7
• Complexity: 46.1
• Transport DOT Label: Poison

Purity/Quality:

99% ^*data from raw suppliers

Aniline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T, N, F
• Hazard Codes: T,N,F
• Statements: 23/24/25-40-41-43-48/23/24/25-50-68-48/20/21/22-39/23/24/25-11
• Safety Statements: 26-27-36/37/39-45-46-61-63-36/37-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Amines, Aromatic
• Canonical SMILES: C1=CC=C(C=C1)N
• Inhalation Risk: A harmful contamination of the air will be reached on evaporation of this substance at 20 °C; on spraying or dispersing, however, much faster.
• Effects of Short Term Exposure: The substance is severely irritating to the eyes. The substance may cause effects on the blood. This may result in the formation of methaemoglobin. Exposure could cause haemolysis. This may result in haemolytic anaemia. The effects may be delayed. Medical observation is indicated.
• Effects of Long Term Exposure: Repeated or prolonged contact may cause skin sensitization. The substance may have effects on the blood. This may result in haemolytic anaemia.
• 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. First produced in 1826 by Otto Unverdorben through destructive distillation of indigo, the first industrial use was as a purple dye, Mauveine, formulated by William Henry Perkin accidentally in an attempt to isolate quinone. The name aniline was given in deference to the indigoyielding plant, Indigofera suffruticosa, commonly named anil.
• Uses: Aniline is an important industrial chemical for many decades. Currently, it is most widely used for the manufacture of polyurethanes and rubber, with lesser amounts consumed in the production of pesticides (herbicides, fungicides, insecticides, animal repellants), defoliants, dyes, antioxidants, antidegradants, and vulcanization accelerators. It is also an ingredient of some household products, such as polishes (stove and shoe), paints, varnishes, and marking inks. 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. 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. 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.
• 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).

Technology Process of Aniline

There total 3979 articles about Aniline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 22.0%

C18H23NO3Si (99391-13-6) → 4-methoxybenzoic acid (100-09-4) + aniline (62-53-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; Ambient temperature;

DOI:10.1039/c39880001530

Reference yield: 14.0%

cyclohexane (110-82-7,25012-93-5) + 1-(benzyloxy)-1H-benzo[d][1,2,3]triazole (68930-15-4) → 1,2,3-Benzotriazole (95-14-7,27556-51-0) + cyclohexylcyclohexane (92-51-3) + N-phenyl-2-cyclohexylamine (1821-36-9) + benzaldehyde (100-52-7) + aniline (62-53-3) + Azobenzene (1227476-15-4)

Guidance literature:

for 8h; Product distribution; Irradiation;

Reference yield:

p-nitrophenylbenzotriazene (13113-75-2) + Benzenesulfinic acid (618-41-7) → 4-nitro-aniline (100-01-6,104810-17-5) + aniline (62-53-3) + phenylazo phenyl sulfone (14922-16-8)

Guidance literature:

upstream raw materials:

diazomethane

diethyl ether

N-Phenylhydroxylamine

piperidine

Downstream raw materials:

phenyl-(tetrahydropyran-2-yl)amine

N,N-diphenylbenzamidine

5-anilino-penta-2,4-dienal-phenylimine

glutacondianil hydrochloride

Refernces

• 1、 Portsmouth,Beal. "-". . p. 451,453-456. Retrieved 1971.
• 2、 Wibaut. "-". . p. 545. Retrieved 1917.
• 3、 Kondeboina, Murali,Enumula, Siva Sankar,Gurram, Venkata Ramesh Babu,Yadagiri, Jyothi,Burri, David Raju,Kamaraju, Seetha Rama Rao. "Mesoporous silica supported cobalt catalysts for gas phase hydrogenation of nitrobenzene: role of pore structure on stable catalytic performance". . p. 15714 - 15725. Retrieved 2018.
• 4、 Liu, Juanjuan,Zou, Shihui,Xiao, Liping,Fan, Jie. "Well-dispersed bimetallic nanoparticles confined in mesoporous metal oxides and their optimized catalytic activity for nitrobenzene hydrogenation". . p. 441 - 446. Retrieved 2014.
• 5、 Sakaki, Shigcyoshi,Koga, Hiroaki,Tao, Kou-Ichiro,Yamashita, Takafumi,Iwashita, Tetsuro,Hamada, Taisuke. "Efficient reduction catalysis of viologen-bound iron porphyrin and its application to six-electron reduction of nitrobenzene to aniline". . p. 1015 - 1017. Retrieved 2000.
• 6、 Kuhn, L. P.,Corwin, A. H.. "". . p. 3370 - 3375. Retrieved 1948.
• 7、 Shim, Sang Chul,Choi, Kui Nam,Yeo, Young Kuk. "Transition Metal Catalyzed Reduction of Azidoarenes to Aminoarenes with Carbon Monoxide-Water System". . p. 1149 - 1150. Retrieved 1986.
• 8、 Cai, Mei Qiang,Wei, Xiao Qin,Song, Zhi Jun,Jin, Mi Cong. "Decolorization of azo dye Orange G by aluminum powder enhanced by ultrasonic irradiation". . p. 167 - 173. Retrieved 2015.
• 9、 Yu, Tianhua,Yang, Ruiguang,Xia, Sheng,Li, Guiying,Hu, Changwei. "Direct amination of benzene to aniline with H2O2 and NH3·H2O over Cu/SiO2 catalyst". . p. 3159 - 3167. Retrieved 2014.
• 10、 Xun, Zhan,Feng, Xian,Wang, Jianjun,Shi, Daqing,Huang, Zhibin. "Multicomponent Strategy for the Preparation of Pyrrolo[1,2-a]pyrimidine Derivatives under Catalyst-Free and Microwave Irradiation Conditions". . p. 696 - 702. Retrieved 2016.