4-Aminobenzonitrile

Base Information

• Chemical Name: 4-Aminobenzonitrile
• CAS No.: 873-74-5
• Molecular Formula: C7H6N2
• Molecular Weight: 118.138
• Hs Code.: 2926.90
• European Community (EC) Number: 212-850-1
• NSC Number: 7625
• UNII: PB8V69Y76T
• DSSTox Substance ID: DTXSID0061240
• Nikkaji Number: J46.531C
• Wikidata: Q27286445
• Mol file: 873-74-5.mol

Synonyms:4-aminobenzonitrile;p-aminobenzonitrile;para-aminobenzonitrile

Chemical Property of 4-Aminobenzonitrile

Chemical Property:

• Appearance/Colour: off-white or beige to orange-yellow crystalline
• Vapor Pressure: 0.00263mmHg at 25°C
• Melting Point: 83-85 °C(lit.)
• Refractive Index: 1.59
• Boiling Point: 286.5 °C at 760 mmHg
• PKA: 1.74(at 25℃)
• Flash Point: 127.1 °C
• PSA: 49.81000
• Density: 1.14 g/cm³
• LogP: 1.72168
• Storage Temp.: Store below +30°C.
• Water Solubility.: Soluble in ethyl acetate, dichloromethane and chloroform. Insoluble in water.
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 118.053098200
• Heavy Atom Count: 9
• Complexity: 125

Purity/Quality:

98% ^*data from raw suppliers

4-Aminobenzonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi
• Statements: 22-36-36/37/38-20/21/22
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitriles
• Canonical SMILES: C1=CC(=CC=C1C#N)N
• Uses: 4-Aminobenzonitrile is an amino substituted benzonitrile with hypotensive activity. 4-Aminobenzonitrile is used as radioprotective agent 4-Aminobenzonitrile was used as derivatization reagent in capillary zone electrophoretic analysis of aldoses, ketoses and uronic acid. It was used in the synthesis of methacrylic monomers containing pendant azobenzene structures and polythiophenes containing an azobenzene moiety in the side-chain. 4-Aminobenzonitrile is used as an amino substituted benzonitrile with hypotensive activity and as a radioprotective agent. It is also used as a derivatization reagent in the capillary zone electrophoretic analysis of aldoses, ketoses and uronic acid. Further, it is used in the preparation of methacrylic monomers containing pendant azobenzene structures and polythiophenes containing an azobenzene moiety in the side-chain.

Technology Process of 4-Aminobenzonitrile

There total 208 articles about 4-Aminobenzonitrile 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: 92.0%

4-Cyanochlorobenzene (623-03-0) → 4,4’-dicyanodipehnylamine (36602-05-8) + 4-Aminobenzonitrile (873-74-5)

Guidance literature:

With C₄₆H₇₁Cl₃N₂Pd; ammonia; sodium t-butanolate; In 1,4-dioxane; at 80 ℃; for 2h; Inert atmosphere; Schlenk technique;

DOI:10.1021/acs.organomet.6b00830

Reference yield: 78.0%

4-nitrobenzonitrile (619-72-7) → (4-aminomethyl)aniline (4403-71-8) + 4-Aminobenzonitrile (873-74-5)

Guidance literature:

With isopropyl alcohol; sodium hydroxide; for 12h; chemoselective reaction; Inert atmosphere; Reflux;

DOI:10.1039/c2gc16441h

Reference yield: 46.0%

4-cyano-N,N-dimethylaniline-N-oxide (62820-00-2) + cyclohexene (110-83-8) → 4-cyano-N-methylaniline (4714-62-9) + N,N'-dimethyl-N,N'-bis-(p-cyanophenyl)hydrazine (79121-26-9) + cyclohexane-1,2-epoxide (286-20-4) + N,N'-bis-(p-cyanophenyl)-N-methylmethylenediamine (97860-69-0) + 4-Aminobenzonitrile (873-74-5) + 4-cyano-N,N-dimethylaniline (1197-19-9)

Guidance literature:

With 1H-imidazole; [Mn(2,3,7,8,12,13,17,18-octamethyl-5,10,15,20-tetraphenylporphyrin)Cl]; In dichloromethane; at 25 ℃; Product distribution; Rate constant; with various alkene concentration;

DOI:10.1021/ja00245a039

upstream raw materials:

4-ureidobenzoic acid

4-bromo-aniline

4-nitrobenzonitrile

styrene

Downstream raw materials:

1-(4-cyanophenyl)-3-(4-nitrophenyl)urea

p-methoxybenzylidene-p-cyano-aniline

N-(4-cyanophenyl)-S-phenyl sulfonamide

N-(4-cyano-phenyl)-N'-phenyl-guanidine

Refernces

• 1、 Moldoveanu, Serban C.. "Interconversion of nicotine enantiomers during heating and implications for smoke from combustible cigarettes, heated tobacco products, and electronic cigarettes". . p. 667 - 677. Retrieved 2022/02/02.
• 2、 Ioannou, Dimitris I.,Gioftsidou, Dimitra K.,Tsina, Vasiliki E.,Kallitsakis, Michael G.,Hatzidimitriou, Antonios G.,Terzidis, Michael A.,Angaridis, Panagiotis A.,Lykakis, Ioannis N.. "Selective Reduction of Nitroarenes to Arylamines by the Cooperative Action of Methylhydrazine and a Tris(N-heterocyclic thioamidate) Cobalt(III) Complex". supporting information. p. 2895 - 2906. Retrieved 2021/02/27.