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 
• 591-50-4 iodobenzene 
• 100-01-6 4-nitro-aniline 
• 100-00-5 4-chlorobenzonitrile 
• 62-53-3 aniline 
• 147506-92-1 2,2-diphenyl-1-(2,4,6-trinitrophenyl)hydrazyl 
• 91330-60-8 2-azido-5-nitrobiphenyl 
• 100-02-7 4-nitro-phenol 
• 103-72-0 phenyl isothiocyanate 
• 98-95-3 nitrobenzene 
• 103-84-4 Acetanilid 
• 17763-80-3 para-nitrophenyl triflate 
• 1516-60-5 4-nitrophenyl azide 

Downstream Products

• 7418-39-5 N-(4-nitrophenyl)-N-phenylacetamide 
• 793-24-8 N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine 
• 101-87-1 N-cyclohexyl-N'-phenyl-p-phenylenediamine 
• 101-72-4 N-phenyl-N'-isopropyl-p-phenylenediamine 
• 1100-10-3 4,4'-dinitrotriphenylamine 
• 101-54-2 N-phenylphenylene-1,4-diamine 
• 118989-60-9 N-(4-nitrophenyl)-N-phenyl-2-(4-methyl-1-piperazinyl)acetamide 
• 3077-85-8 3-Nitro-carbazol 
• 194800-37-8 4-fluoro-N-(4-(phenylamino)phenyl)benzamide 
• 3081-01-4 N-(1,4-dimethylpentyl)-N'-phenyl-p-phenylenediamine 

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

Copper nanoparticle anchored biguanidine-modified Zr-UiO-66 MOFs: a competent heterogeneous and reusable nanocatalyst in Buchwald-Hartwig and Ullmann type coupling reactions

We have designed a functionalized metal-organic framework (MOF) of UiO topology as a support, with an extremely high surface area, adjustable pore sizes and stable crystalline coordination polymeric structure and implanted copper (Cu) nanoparticles thereon. The core three dimensional Zr-derived MOF (UiO-66-NH2) was modified with a biguanidine moiety following a covalent post-functionalization approach. The morphological and physicochemical features of the material were determined using analytical methods such as FT-IR, SEM, TEM, EDX, atomic mapping, XRD and ICP-OES. The SEM and XRD results justified the unaffected morphology of Zr-MOF after structural modifications. The as-synthesized UiO-66-biguanidine/Cu nanocomposite was catalytically explored in the aryl and heteroaryl Buchwald-Hartwig C-N and Ullmann type C-O cross coupling reactions with excellent yields. A library of biaryl amine and biaryl ethers was synthesized over the catalyst under mild and green conditions. Furthermore, the catalyst was isolated by centrifugation and recycled 11 times with no significant copper leaching or change in its activity.

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.