N,N'-Diphenyl-p-phenylenediamine

Base Information

• Chemical Name: N,N'-Diphenyl-p-phenylenediamine
• CAS No.: 74-31-7
• Deprecated CAS: 66746-42-7,72711-53-6,943443-44-5,72711-53-6,943443-44-5
• Molecular Formula: C18H16 N2
• Molecular Weight: 260.338
• Hs Code.: 2921.51 Oral rat LD50: 2370 mg/kg
• European Community (EC) Number: 200-806-4
• ICSC Number: 1181
• NSC Number: 5761
• UN Number: 1673
• UNII: DD517SCM92
• DSSTox Substance ID: DTXSID9020538
• Nikkaji Number: J11.021C
• Wikidata: Q22829255
• Pharos Ligand ID: AKTBULNT5QQH
• ChEMBL ID: CHEMBL1333512
• Mol file: 74-31-7.mol

Synonyms:DDPD;DPPD;N,N'-diphenyl-1,4-phenylenediamine;N,N'-diphenyl-4-phenylenediamine;N,N'-diphenyl-p-phenylenediamine

Chemical Property of N,N'-Diphenyl-p-phenylenediamine

Chemical Property:

• Appearance/Colour: light gray to brown powder
• Vapor Pressure: 5.6E-09mmHg at 25°C
• Melting Point: 145 - 152 C
• Refractive Index: 1.6300 (estimate)
• Boiling Point: 220 - 225 C
• PKA: 1.85±0.20(Predicted)
• Flash Point: 297 °C
• PSA: 24.06000
• Density: 1.2
• LogP: 5.31980
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: <0.1 g/100 mL at 20℃
• XLogP3: 5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 260.131348519
• Heavy Atom Count: 20
• Complexity: 231
• Transport DOT Label: Poison

Purity/Quality:

99% ^*data from raw suppliers

N1,N4-Diphenylbenzene-1,4-diamine ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 43-52/53
• Safety Statements: 24-37-61

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)NC3=CC=CC=C3
• Inhalation Risk: A nuisance-causing concentration of airborne particles can be reached quickly when dispersed.
• Effects of Long Term Exposure: Repeated or prolonged contact may cause skin sensitization.
• Description: N,N'-Diphenyl-4-phenylenediamine (DPPD) is a rubber accelerant, formerly contained in the "black rubber mix". The most frequent occupational categories are in metal industry, homemakers, health services and laboratories, and building industries.
• Uses: Polymerization inhibitor. Antioxidant for rubber, petroleum oils, feedstuffs. N1,N4-Diphenylbenzene-1,4-diamine can be used to prepare low pressure change, high temperature resistant flame retardant silicone rubber. N,N'-Diphenyl-4-phenylene diamine is an antioxidant for rubber, petroleum oils, and feed stuffs; stabilizer; a polymerization inhibitor; used to retard copper degradation; as an intermediate for dyes, drugs, plasties and detergents; antidegradant for nitrile-butadiene rubber, natural, styrene-butadiene, isoprene, butadiene, and ehloroprene rubbers.

Technology Process of N,N'-Diphenyl-p-phenylenediamine

There total 49 articles about N,N'-Diphenyl-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: 99.0%

chlorobenzene (108-90-7) + N-phenylphenylene-1,4-diamine (101-54-2) → N,N'-diphenyl-1,4-phenylenediamine (74-31-7,943443-44-5)

Guidance literature:

With dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; chloro[2-(dicyclohexylphosphino)-3,6-dimethoxy-2’,4’,6’-triisopropyl-1,1’-biphenyl] [2-(2-aminoethyl)phenyl]palladium(II); sodium t-butanolate; In 1,4-dioxane; at 80 ℃; for 2h; chemoselective reaction; Inert atmosphere;

DOI:10.1021/ja8055358

Reference yield: 94.4%

N4-(2-methylphenyl) benzene-1,4-diamine (66311-46-4) + N-phenylphenylene-1,4-diamine (101-54-2) + phenol (108-95-2,27073-41-2) → N,N'-diphenyl-1,4-phenylenediamine (74-31-7,943443-44-5) + N-phenyl-N'-tolyl-p-phenylenediamine (27173-16-6)

Guidance literature:

With 5%-palladium/activated carbon; In cyclohexanone; at 250 ℃; for 6h; Autoclave; Inert atmosphere;

Reference yield: 93.6%

N-phenylphenylene-1,4-diamine (101-54-2) + phenol (108-95-2,27073-41-2) → N,N'-diphenyl-1,4-phenylenediamine (74-31-7,943443-44-5)

Guidance literature:

With 5%-palladium/activated carbon; In cyclohexanone; at 220 ℃; for 6h; Concentration; Autoclave; Inert atmosphere;

upstream raw materials:

N,N'-diphenyl-1,4-phenylenediamine

4-amino-phenol

aniline

1.4-dibromobenzene

Downstream raw materials:

N-isopropyl-N'-phenyl-1,4-benzoquinonediimine

diphenyl p-phenylenediamine

(4-anilino-phenyl)-phenyl-aminyl

N,N'-diphenyl-1,4-phenylenediamine

Refernces

• 1、 Varlamov. "Effect of Propanol-1 on the Reaction between Thiophenol and N,N'-Diphenyl-1,4-Benzoquinone Diimine in Chlorobenzene". . p. 644 - 651. Retrieved 2019.
• 2、 -. "Preparation method of diaryl p-phenylenediamine anti-aging agent". Paragraph 0069-0076. . Retrieved 2020/02/10.