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 
• 104-04-1 N-(4-Nitrophenyl)acetamide 
• 73333-79-6 N-(4-nitrophenyl)-N-phenylbenzamide 
• 591-50-4 iodobenzene 
• 100-01-6 4-nitro-aniline 
• 100-00-5 4-chlorobenzonitrile 
• 62-53-3 aniline 
• 148-97-0 N-hydroxy-N-nitroso-benzenamine 
• 71-43-2 benzene 
• 91330-60-8 2-azido-5-nitrobiphenyl 
• 56751-83-8 diphenylsulfamoyl chloride 
• 100-02-7 4-nitro-phenol 
• 103-72-0 phenyl isothiocyanate 
• 98-95-3 nitrobenzene 

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 
• 861578-86-1 N-(4-nitro-phenyl)-N,N'-diphenyl-urea 
• 793-24-8 N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine 
• 101-72-4 N-phenyl-N'-isopropyl-p-phenylenediamine 
• 101-87-1 N-cyclohexyl-N'-phenyl-p-phenylenediamine 
• 13744-88-2 N‐methyl‐N‐(4‐nitrophenyl)benzenamine 
• 7402-56-4 N-[4-(phenylamino)phenyl]formamide 
• 4316-57-8 4-nitrophenyldiphenylamine 
• 73333-79-6 N-(4-nitrophenyl)-N-phenylbenzamide 
• 118989-60-9 N-(4-nitrophenyl)-N-phenyl-2-(4-methyl-1-piperazinyl)acetamide 

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

Cu(OAc)2-porphyrins as an efficient catalytic system for base-free, nature mimicking Chan–Lam coupling in water

The use of porphyrins as ligands in organic synthesis reveals the natural process, because these are the constituent motifs of catalysts in many bio-organic reactions. This article presents the synthesis of two N-pincer tetradentate porphyrins; tetrasodium meso-tetra(p-sulfonatophenyl)phorphyrin (H2TSTpSPP) and meso-tetra(m-carboxyphenyl)porphyrin (H2TmCPP), and study on their aptness for Cu-catalyzed C–N coupling reactions of arylboronic acids and amines (Chan–Lam coupling reaction) in water under external base free conditions. The porphyrins and Chan–Lam coupling products were well characterized by their spectral analysis. The high product yields, application of nature-inspired conditions, large extent of substrates, ease of making and handling the ligands, avoidance of base, and use of water as reaction media are the attractive attributes of this finding.

A terphenyl phosphine as a highly efficient ligand for palladium-catalysed amination of aryl halides with 1° anilines

A terphenyl phosphine ligand (2,6-bis(2,4,6-triisopropylphenyl)phenyl-dicyclohexylphosphine, TXPhos) and its supported palladium complex [(TXPhos)(allyl)PdCl] have been developed and the catalyst system is highly efficient in amination of aryl halides with 1° anilines, especially effective for densely functionalized substrates including both partners possessing ortho-ester, acetyl, nitrile and nitro groups. With the TXPhos-supported catalyst system, many partner combinations have been unprecedentedly realized and the base scope has been even extended to KOAc, which is even the best choice in the amination of 2-nitrochlorobenzene.