N-Phenyl-p-phenylenediamine

Base Information

• Chemical Name: N-Phenyl-p-phenylenediamine
• CAS No.: 101-54-2
• Deprecated CAS: 12227-74-6,76600-63-0,2365226-94-2,76600-63-0
• Molecular Formula: C12H12N2
• Molecular Weight: 184.241
• Hs Code.: 2921.51
• European Community (EC) Number: 202-951-9
• ICSC Number: 1446
• NSC Number: 37074,3401
• UN Number: 1673
• UNII: 007X4XXS71
• DSSTox Substance ID: DTXSID7025895
• Nikkaji Number: J4.017G
• Wikipedia: 4-Aminodiphenylamine
• Wikidata: Q4533362
• Metabolomics Workbench ID: 60364
• ChEMBL ID: CHEMBL572203
• Mol file: 101-54-2.mol

Synonyms:4-aminodiphenylamine;4-aminodiphenylamine monohydrochloride;4-aminodiphenylamine sulfate;4-aminodiphenylamine sulfate (2:1);N-phenyl-1,4-benzenediamine;N-phenyl-p-phenylenediamine;p-aminodiphenylamine;p-anilinoaniline;para-aminodiphenylamine;Semidine

Chemical Property of N-Phenyl-p-phenylenediamine

Chemical Property:

• Appearance/Colour: Odorless purple-black solid or flake or dark purple chips
• Vapor Pressure: 0.000171mmHg at 25°C
• Melting Point: 69 °C
• Refractive Index: 1.656
• Boiling Point: 354.7 °C at 760 mmHg
• PKA: 5.20±0.10(Predicted)
• Flash Point: 197.8 °C
• PSA: 38.05000
• Density: 1.09 g/cm³
• LogP: 3.66660
• Storage Temp.: Store below +30°C.
• Solubility.: ethanol: soluble10mg/mL, clear, very dark red (Violet to brown t
• Water Solubility.: Soluble in water at 20°C 0.6g/L. Soluble in (10 mg/mL) ethanol.
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 184.100048391
• Heavy Atom Count: 14
• Complexity: 156
• Transport DOT Label: Poison

Purity/Quality:

96%, ^*data from raw suppliers

N-?Phenyl-?p-?phenylenediamine(p-Anilinoaniline) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi,N
• Statements: 22-36-43-42/43-36/37/38-20/22-50/53
• Safety Statements: 26-36-45-36/37/39-61-60-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Amines, Polyaromatic
• Canonical SMILES: C1=CC=C(C=C1)NC2=CC=C(C=C2)N
• Inhalation Risk: A harmful concentration of airborne particles can be reached quickly when dispersed, especially if powdered.
• Effects of Short Term Exposure: The substance is irritating to the skin and eyes. Ingestion could cause effects on the blood. This may result in the formation of methaemoglobin. Medical observation is indicated. The effects may be delayed.
• Effects of Long Term Exposure: Repeated or prolonged contact may cause skin sensitization.
• Description: p-Aminodiphenylamine hydrochloride was formerly used as a hair dye. Sensitization, when deteeted by patch testing, is relatively low in hairdressers.
• Uses: Dye intermediate, pharmaceuticals, photographic chemicals. 4-Aminodiphenylamine is used as an oxidation dye color in hair dyes. It is also promoted as an efficient reagent for oxidase enzymes, including glucose, lactate, xanthine, and lysine oxidases. p-Anilinoaniline is an antioxidant that has shown to cause a reduction of NOx emissions from soybean biodiesel powered DI diesel engines but has increased CO and HC emissions. It is also used to produce dyes, pharmaceuticals, and photographic chemicals and frmerly used as a hair dye.

Technology Process of N-Phenyl-p-phenylenediamine

There total 124 articles about N-Phenyl-p-phenylenediamine 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: 29.0%

N-phenyl-N'-phenylthio-p-benzoquinone di-imine (82993-63-3) → N-phenyl-N'-phenylthio-p-phenylenediamine (88047-04-5) + diphenyldisulfane (882-33-7) + N-phenylphenylene-1,4-diamine (101-54-2)

Guidance literature:

With sodium dithionite; for 2h; Ambient temperature;

Reference yield: 21.2%

tetrachloromethane (56-23-5) + aniline (62-53-3) → N,N',N''-triphenylguanidine (101-01-9) + diphenyl hydrazine (122-66-7) + phenylcarbonimidic dichloride (622-44-6) + Azobenzene (1227476-15-4) + N-phenylphenylene-1,4-diamine (101-54-2) + N-phenyl-1,2-benzenediamine (534-85-0)

Guidance literature:

at 15 ℃; for 24h; Product distribution; Mechanism; Irradiation; also in methanol and 1,4-dioxane;

Reference yield: 18.6%

dichloromethane (75-09-2) + aniline (62-53-3) → N-methylenebenzenamine (100-62-9) + methylene chloride (74-87-3) + 1,2-dichloro-ethane (107-06-2,52399-93-6) + Azobenzene (1227476-15-4) + N-phenylphenylene-1,4-diamine (101-54-2) + N-phenyl-1,2-benzenediamine (534-85-0)

Guidance literature:

at 15 ℃; for 24h; Product distribution; Mechanism; Irradiation;

upstream raw materials:

diethyl ether

hydrogen bromide

diphenyl hydrazine

acetic acid

Downstream raw materials:

piperonal-(4-anilino-phenylimine)

1-phenyl-3-[4-(phenylamino)phenyl]urea

N-(4-nitrophenyl)-N'-phenyl-1,4-phenylenediamine

N-phenyl-N'-isopropyl-p-phenylenediamine

Refernces

• 1、 Buchwald, Stephen L.,Mauger, Christelle,Mignani, Gerard,Scholz, Ulrich. "Industrial-scale palladium-catalyzed coupling of aryl halides and amines - A personal account". . p. 23 - 39. Retrieved 2006.
• 2、 Gao, Ping,Gosztola, David,Weaver, Michael J.. "Surface-Enhanced Raman Spectroscopy as a Probe of Electroorganic Reaction Pathways. 2. Ring-Coupling Mechanisms during Aniline Oxidation". . p. 3753 - 3760. Retrieved 1989.
• 3、 Stern, Michael K.,Cheng, Brian K.,Hileman, Frederick D.,Allman, James M.. "A New Route to 4-Aminodiphenylamine via Nucleophilic Aromatic Substitution for Hydrogen: Reaction of Aniline and Azobenzene". . p. 5627 - 5632. Retrieved 1994.
• 4、 Polenov,Egorova,Ryazantseva. "Reduction of 4-nitrosodiphenylamine with sodium hydroxy- and aminoalkanesulfinates". . p. 1787 - 1791. Retrieved 2003.
• 5、 Stuehr, Dennis J.,Marletta, Michael A.. "Superoxide-Promoted Oxidation Reactions of Aniline and N-Methylaniline in Dimethyl Sulfoxide". . p. 694 - 696. Retrieved 1985.
• 6、 Seyedi, Neda,Zahedifar, Mahboobeh. "Chitosan nanoparticles functionalized poly-2-hydroxyaniline supported CuO nanoparticles: An efficient heterogeneous and recyclable nanocatalyst for N-arylation of amines with phenylboronic acid at ambient temperature". . . Retrieved 2021.
• 7、 Deng, Haiteng,Van Berkel, Gary J.. "Electrochemical polymerization of aniline investigated using on-line electrochemistry/electrospray mass spectrometry". . p. 4284 - 4293. Retrieved 1999.
• 8、 Petr,Dunsch. "Kinetics of the p-aminodiphenylamine radical in organic solution: An electrochemical and electron spin resonance study". . p. 4867 - 4872. Retrieved 1996.
• 9、 Viveki, Amol B.,Garad, Dnyaneshwar N.,Gonnade, Rajesh G.,Mhaske, Santosh B.. "Para -Selective copper-catalyzed C(sp2)-H amidation/dimerization of anilides via a radical pathway". . p. 1565 - 1568. Retrieved 2020/02/13.