836-30-6

Basic information

• Product Name: 4-Nitrodiphenylamine
• Synonyms: (4-NITROPHENYL)PHENYLAMINE;4-NITRODIPHENYLAMINE;4-NITRO-N-PHENYLANILINE;P-NITRODIPHENYLAMINE;TIMTEC-BB SBB008055;4-Nitrodiphenylamine, 98+%;ANILINE,4-NITRO-N-PHENYL;4-Nitro-N-phenylanilin
• CAS NO: 836-30-6
• Molecular Formula: C₁₂H₁₀N₂O₂
• Molecular Weight: 214.22
• EINECS: 212-646-2
• Product Categories: Intermediates of Dyes and Pigments;Aromatics Compounds;Aromatics;Amines;C11 to C38;Nitrogen Compounds
• Mol File: 836-30-6.mol
• Article Data: 197

Chemical Properties

• Melting Point: 132-135 °C(lit.)
• Boiling Point: 211 °C (30 mmHg)
• Flash Point: 190°C
• Appearance: Orange Crystalline Solid
• Density: 1.2042 (rough estimate)
• Vapor Pressure: 4.68E-06mmHg at 25°C
• Refractive Index: 1.6660 (estimate)
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: -2.60±0.20(Predicted)
• Water Solubility: INSOLUBLE
• BRN: 2051910
• CAS DataBase Reference: 4-Nitrodiphenylamine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Nitrodiphenylamine(836-30-6)
• EPA Substance Registry System: 4-Nitrodiphenylamine(836-30-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-36
• RIDADR: 3077
• WGK Germany: 3
• RTECS: JJ9600000
• TSCA: Yes
• HazardClass: 9
• PackingGroup: III
• Hazardous Substances Data: 836-30-6(Hazardous Substances Data)

Usage

Chemical Properties

Orange Crystalline Solid

Uses

4-Nitrodiphenylamine was used to study reduction of nitrated diphenylamine derivatives in sediment water batch enrichments and dense cell suspensions of anaerobic, aromatic-compound-mineralizing pure bacterial cultures.

Synthesis Reference(s)

The Journal of Organic Chemistry, 42, p. 1786, 1977 DOI: 10.1021/jo00430a025

General Description

4-Nitrodiphenylamine undergoes heterogeneous catalytic transfer hydrogenation to form p-phenylenediamines. 4-Nitrodiphenylamine is used as stabilizer for propellants and explosives.

Purification Methods

Crystallise the amine from EtOH or aqueous EtOH (m 135-136o) and has m 131.5-132o after sublimation in vacuo. [Beilstein 12 H 715, 12 III 1586.]

InChI:InChI=1/C12H10N2O2/c15-14(16)12-8-6-11(7-9-12)13-10-4-2-1-3-5-10/h1-9,13H

Upstream product

• 108-86-1 bromobenzene 
• 591-50-4 iodobenzene 
• 100-01-6 4-nitro-aniline 
• 100-00-5 4-chlorobenzonitrile 
• 62-53-3 aniline 
• 91330-60-8 2-azido-5-nitrobiphenyl 
• 7664-41-7 ammonia 
• 98-95-3 nitrobenzene 
• 34839-24-2 N,N'-bis-(4-nitro-phenyl)-N,N'-diphenyl-hydrazine 
• 7664-93-9 sulfuric acid 
• 636-98-6 p-nitrobenzene iodide 
• 1798-11-4 4-nitrophenoxyacetic acid 
• 102-07-8 bis(diphenyl)urea 
• 586-78-7 para-nitrophenyl bromide 

Downstream Products

• 40932-71-6 4-bromo-N-(4-nitrophenyl)aniline 
• 1821-27-8 N,N-bis(p-nitrophenyl)amine 
• 612-36-2 2-nitro-N-(4-nitrophenyl)benzenamine 
• 101-54-2 N-phenylphenylene-1,4-diamine 
• 7418-39-5 N-(4-nitrophenyl)-N-phenylacetamide 
• 7402-56-4 N-[4-(phenylamino)phenyl]formamide 
• 1100-10-3 4,4'-dinitrotriphenylamine 
• 3081-01-4 N-(1,4-dimethylpentyl)-N'-phenyl-p-phenylenediamine 
• 13744-88-2 N‐methyl‐N‐(4‐nitrophenyl)benzenamine 
• 1417726-07-8 1-(benzo[d][1,3]dioxol-5-yl)-3-(4-nitroaniline)propan-2-ol 
• 4117-90-2 bis(4-aminophenyl)phenylamine 

Relevant articles and documents

Diarylamine Synthesis via Desulfinylative Smiles Rearrangement

Diarylamines are obtained directly from sulfinamides through a novel rearrangement sequence. The transformation is transition metal-free and proceeds under mild conditions, providing facile access to highly sterically hindered diarylamines that are otherw

A quinoxaline-based porous organic polymer containing copper nanoparticles CuNPs@Q-POP as a robust nanocatalyst toward C-N coupling reaction

A novel porous organic polymer (denoted by Q-POP) was successfully fabricated by free-radical copolymerization of allyl-substituted 2,3-di(2-hydroxyphenyl)1,2-dihydroquinoxaline, and divinylbenzene under solvothermal conditions and used as a new platform for immobilization of copper nanoparticles. The CuNPs@Q-POP nanocatalyst was prepared via incorporating of Cu(NO3)2 into the polymeric network, followed by the reduction of Cu2+ ion with hydrazine hydrate. The obtained materials were characterized through FT-IR, XRD, N2 adsorption-desorption isotherms, ICP, TGA, SEM, HR-TEM, EDX, and the single-crystal X-ray crystallography. The results displayed that Q-POP and CuNPs@Q-POP possessed high surface area, hierarchical porosity, and excellent thermal and chemical stability. The as-synthesized catalyst was utilized for the Ullmann C-N coupling reaction of aromatic amines and different aryl halides to prepare various diarylamine derivatives. All types of aryl halides (except aryl fluorides) were screened in the Ullmann C-N coupling reaction with aromatic amines to produce diaryl amines in good to excellent yields (50-98%), and it turned out that aryl iodides have the best results. Besides, due to the strong interactions between CuNPs, N, and O-atoms of quinoxaline moiety existing in the polymeric framework, the copper leaching from the support was not observed. Furthermore, the catalyst was recycled and reused for five consecutive runs without significant activity loss.

Copper anchored on phosphorus g-C3N4as a highly efficient photocatalyst for the synthesis ofN-arylpyridin-2-amines

A heterogeneous photocatalyst based on copper modified phosphorus doped g-C3N4(Cu/P-CN) has been prepared and characterized. This recyclable catalyst exhibited high photocatalytic activity for the synthesis ofN-arylpyridin-2-amine derivatives by the reaction of 2-aminopyridine and aryl boronic acid at room temperature under the irradiation of blue light. Importantly, the range of substrates for this coupling reaction has been expanded to include aryl boronic acids with strong electron-withdrawing groups as viable raw materials. In addition, this heterogeneous catalyst can be used at least 6 times while maintaining its catalytic activity.