Diphenylamine

Base Information

• Chemical Name: Diphenylamine
• CAS No.: 122-39-4
• Deprecated CAS: 1135443-74-1,86352-05-8
• Molecular Formula: C12H11N
• Molecular Weight: 169.226
• Hs Code.: H5)2NH MOL WT. 169.23
• European Community (EC) Number: 204-539-4
• ICSC Number: 0466
• NSC Number: 215210
• UN Number: 2811,3077
• UNII: 9N3CBB0BIQ
• DSSTox Substance ID: DTXSID4021975
• Nikkaji Number: J2.493G
• Wikipedia: Diphenylamine
• Wikidata: Q412265
• Metabolomics Workbench ID: 45607
• ChEMBL ID: CHEMBL38688
• Mol file: 122-39-4.mol

Synonyms:Diphenylamine

Chemical Property of Diphenylamine

Chemical Property:

• Appearance/Colour: white crystals or powder
• Vapor Pressure: 1 mm Hg ( 108 °C)
• Melting Point: 52 °C
• Refractive Index: 1.634
• Boiling Point: 302 °C at 760 mmHg
• PKA: 0.79(at 25℃)
• Flash Point: 152.8 °C
• PSA: 12.03000
• Density: 1.088 g/cm³
• LogP: 3.50320
• Storage Temp.: 0-6°C
• Sensitive.: Air & Light Sensitive
• Solubility.: alcohol: passes test
• Water Solubility.: Slightly soluble. 0.03 g/100 mL
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 169.089149355
• Heavy Atom Count: 13
• Complexity: 116
• Transport DOT Label: Poison

Purity/Quality:

99% ^*data from raw suppliers

Diphenylamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,N,F
• Hazard Codes: T,N,F
• Statements: 23/24/25-33-50/53-52/53-39/23/24/25-11-51/53
• Safety Statements: 28-36/37-45-60-61-28A-16-7

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Amines, Polyaromatic
• Canonical SMILES: C1=CC=C(C=C1)NC2=CC=CC=C2
• Inhalation Risk: Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly.
• Effects of Short Term Exposure: The substance is irritating to the eyes and respiratory tract.
• Effects of Long Term Exposure: The substance may have effects on the kidneys. This may result in impaired functions. The substance may have effects on the blood. This may result in anaemia.
• Description: Solutions of diphenylamine are used to treat apples a few days before harvest. Residue on apples’ surfaces of 10 ppm is permitted by regulation in Australia, Canada, and the United States.
• Uses: Diphenylamine is an aromatic amine that was shown to exhibit antioxidant activities and is now used as an anti-scald agent. It is also used in the manufacture of a variety of substances, for instance, dye stuffs and their intermediates, pesticides, anthelmintic drugs, and as reagents in analytical chemistry laboratories. Diphenylamine is used in the manufactureof dyes, as a stabilizer for nitrocelluloseexplosives, and as an analytical reagent forcolorimetric tests for nitrate and chlorate.Other applications of this compoundinclude preventing postharvest deteriorationof apple and peer crops; as an antioxidant inrubber and elastomer industry and in the per fumery. As a stabilizer for propellants andexplosives, it binds their degradation prod ucts thus prolonging the storage time of suchpropellants. Diphenylamine is used post-harvest to prevent superficial scald in apples in cold store.

Technology Process of Diphenylamine

There total 728 articles about Diphenylamine 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: 85.0%

phenol (108-95-2,27073-41-2) → N-phenyl-2-cyclohexylamine (1821-36-9) + diphenylamine (122-39-4)

Guidance literature:

With palladium on activated carbon; sodium formate; hydrazine hydrate; trifluoroacetic acid; In toluene; at 150 ℃; for 24h; Temperature; Sealed tube; Inert atmosphere;

DOI:10.1002/adsc.201700712

Reference yield: 65.0%

N-cyclohexyl-cyclohexanamine (101-83-7) → N-phenyl-2-cyclohexylamine (1821-36-9) + diphenylamine (122-39-4)

Guidance literature:

With ethene; 5%-palladium/activated carbon; In 5,5-dimethyl-1,3-cyclohexadiene; at 150 ℃; for 24h; under 760.051 Torr; Molecular sieve; Autoclave;

DOI:10.1002/adsc.201800504

Reference yield: 40.0%

cyclohexanone-oxime (100-64-1) → N-phenyl-2-cyclohexylamine (1821-36-9) + cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) + diphenylamine (122-39-4) + aniline (62-53-3)

Guidance literature:

With Pd(OH)x/Al₂O₃; In N,N-dimethyl acetamide; at 130 ℃; for 3h; Schlenk technique; Inert atmosphere;

DOI:10.1021/jacs.7b07347

upstream raw materials:

acetamide

bromobenzene

tetrachloromethane

N,N,N'-triphenylhydrazine

Downstream raw materials:

2-chloro-N,N-diphenylbenzamide

2,2-bis-(4-anilino-phenyl)-propane

2-hydroxy-N,N-diphenylbenzamide

bis-(4-trityl-phenyl)-amine

Refernces

• 1、 Chen, Zheng,Wang, Shuo,Lian, Chao,Liu, Yuxi,Wang, Dingsheng,Chen, Chen,Peng, Qing,Li, Yadong. "Nano PdAu Bimetallic Alloy as an Effective Catalyst for the Buchwald-Hartwig Reaction". . p. 351 - 355. Retrieved 2016.
• 2、 Ma, Ruixuan,Qin, Jianhua,Shi, Lei,Zhang, Xinhai. "A base-free Chan–Lam reaction catalyzed by an easily assembled Cu(II)-carboxylate metal-organic framework". . p. 795 - 799. Retrieved 2021.
• 3、 Mazaletskaya, L. I.,Karpukhina, G. V.. "THE REACTION OF DIPHENYLAMINYL AND NITROXYL RADICALS AND THEIR ROLE IN THE MECHANISM OF THE ANTIOXIDANT EFFECT OF MIXTURES OF AN AROMATIC AMINE WITH ANTIOXIDANT". . p. 246 - 250. Retrieved 1983.
• 4、 Primo, Ana,Esteve-Adell, Ivan,Coman, Simona N.,Candu, Natalia,Parvulescu, Vasile I.,Garcia, Hermenegildo. "One-Step Pyrolysis Preparation of 1.1.1 Oriented Gold Nanoplatelets Supported on Graphene and Six Orders of Magnitude Enhancement of the Resulting Catalytic Activity". . p. 607 - 612. Retrieved 2016.
• 5、 Hardouin Duparc, Valérie,Dimeck, Clémentine,Schaper, Frank. "Replacing sulfonate by carboxylate: Application of pyridyliminocarboxylato copper(II) complexes in rac-lactide polymerization and Chan-Evans-Lam coupling". . p. 178 - 190. Retrieved 2019.
• 6、 Moran, Ricardo J.,Cramer, Christopher,Falvey, Daniel E.. "Reactions of Diarylnitrenium Ions with Electron Rich Alkenes: An Experimental and Theoretical Study". . p. 2742 - 2751. Retrieved 1997.
• 7、 Morarji, Devita V.,Gurjar, Kamlesh K.. "Theoretical and Experimental Studies: Cu(I)/Cu(II) Catalytic Cycle in CuI/Oxalamide-Promoted C-N Bond Formation". . . Retrieved 2019.
• 8、 Liu, Bo,Liu, Bin,Zhou, Yongbo,Chen, Wanzhi. "Copper(II) hydroxide complexes of N-heterocyclic carbenes and catalytic oxidative amination of arylboronic acids". . p. 1457 - 1464. Retrieved 2010.
• 9、 Burgers, M. H. W.,Bekkum, H. van. "Vapour-Phase Substitution of Chlorobenzene with Ammonia Catalyzed by Copper-Exchanged Zeolites". . p. 68 - 75. Retrieved 1994.
• 10、 Sajitha,Prathapan,Unnikrishnan. "Novel Burgess reagent mediated C-to-N aryl migration reaction in nitrones". . p. 44689 - 44691. Retrieved 2014.