101-75-7

Basic information

• Product Name: 4-(PHENYLAZO)DIPHENYLAMINE
• Synonyms: 4-(phenylamino)azobenzene;4-(phenylazo)-diphenylamin;4-anilino-azobenzen;Azobenzene, 4-anilino-;Diphenylamine, 4-(phenylazo)-;N-Phenyl-4-[(E)-phenyldiazenyl]aniline;N-Phenyl-4-aminoazobenzene;4-Azobenzeneaniline
• CAS NO: 101-75-7
• Molecular Formula: C₁₈H₁₅N₃
• Molecular Weight: 273.33
• EINECS: 202-972-3
• Product Categories: Anilines, Aromatic Amines and Nitro Compounds;Azo
• Mol File: 101-75-7.mol
• Article Data: 8

Chemical Properties

• Melting Point: 87-91 °C
• Boiling Point: 406.35°C (rough estimate)
• Flash Point: 227 °C
• Appearance: Orange/Fine Crystalline Powder
• Density: 1.0332 (rough estimate)
• Vapor Pressure: 5.74E-07mmHg at 25°C
• Refractive Index: 1.5480 (estimate)
• Solubility: Solubility Insoluble in water; soluble in ethanol, methanol
• PKA: 0.42(at 25℃)
• BRN: 749359
• CAS DataBase Reference: 4-(PHENYLAZO)DIPHENYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(PHENYLAZO)DIPHENYLAMINE(101-75-7)
• EPA Substance Registry System: 4-(PHENYLAZO)DIPHENYLAMINE(101-75-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: 3234
• WGK Germany: 1
• RTECS: JK0185000
• TSCA: Yes
• Hazardous Substances Data: 101-75-7(Hazardous Substances Data)

Usage

Chemical Properties

orange fine crystalline powder

Uses

4-(Phenylazo)diphenylamine is a soluble azo dye and stain. Dyes and metabolites.

Safety Profile

Poison by intravenous route. When heated to decomposition it emits toxic vapors of NOx.

Purification Methods

Purify the dye by chromatography on neutral alumina using dry *C6H6 with 1% of dry MeOH. The major component, which gave a stationary band, is cut out and eluted with EtOH or MeOH. [H.gfeldt & Bigeleisen J Am Chem Soc 82 15 1960.] It crystallises from pet ether, EtOH or aqueous EtOH, and has max at 420nm ( 28,000) (aqueous EtOH) and 540nm (aqueous EtOH/H2SO4) [Badger et al. J Chem Soc 1888 1954, Beilstein 16 H 314, 16 III 343, 16 IV 457.]

InChI:InChI=1/C20H17N/c1-3-7-17(8-4-1)15-21-16-18-11-13-20(14-12-18)19-9-5-2-6-10-19/h1-14,16H,15H2/b21-16+

Upstream product

• 10296-38-5 4-azidopyridine N-oxide 
• 62-53-3 aniline 
• 60544-72-1 [1,4]benzoquinone-mono-[phenyl-(4-phenylazo-phenyl)-hydrazone] 
• 17082-12-1 trans-azobenzene 
• 537-67-7 diphenylamine hydrochloride 
• 122-39-4 diphenylamine 
• 19116-35-9 triphenyl-triazene 
• 100-34-5 benzene diazonium chloride 
• 2684-02-8 benzenediazonium 
• 123703-80-0 C₈₄H₈₀N₈O₈ 
• 622-37-7 Phenyl azide 
• 1227476-15-4 Azobenzene 
• 98-95-3 nitrobenzene 

Downstream Products

• 101-72-4 N-phenyl-N'-isopropyl-p-phenylenediamine 
• 69272-46-4 5,12-diphenyl-5,12-dihydroquinoxalino[2,3-b]phenazine 
• 609848-08-0 4'-{N-(biphenyl-4-yl)-N-[4-(phenylazo)phenyl]amino}-4-vinylbiphenyl 
• 609848-14-8 4-[N-(4-bromophenyl)-N-(biphenyl-4-yl)amino]azobenzene 
• 101-54-2 N-phenylphenylene-1,4-diamine 
• 20199-99-9 nitroso-phenyl-(4-phenylazo-phenyl)-amine 
• 788-17-0 N-phenyl-N'-(1,4-dimethylpentyl)-p-phenylenediamine 
• 4435-12-5 azophenin 
• 4935-81-3 2,3,7-trianilino-5-phenyl-phenazinium; chloride 
• 101-87-1 N-cyclohexyl-N'-phenyl-p-phenylenediamine 

Relevant articles and documents

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Process for preparing aromatic azo and hydrazo compounds, aromatic amides and aromatic amines

A process for producing amino or amido substituted aromatic azo or hydrazo compounds, or aminoaromatic amines, or aminoaromatic amides, or mixtures thereof, comprises the steps of: (a) bringing into reactive contact in a suitable solvent system a nucleophilic compound selected from the group of aniline, substituted aniline derivatives, aliphatic amines, substituted aliphatic amine derivatives, amides and substituted amide derivatives with an azo containing compound; and (b) reacting the nucleophilic compound and the azo containing compound in a confined zone at a suitable time, pressure and temperature.

Electronic spectra of push-pull 4-phenylaminoazobenzene derivatives

A series of push-pull type 4-phenylaminoazobenzene derivatives bearing an electron-withdrawing 4'-substituent were probed by electronic spectra in solution. The visible absorption maxima of these azobenzenes were correlated with the solvent parameters through the McRae theory as well as the solvent donor numbers. While the absorption spectra of these neutral species were solvent-dependent, those of protonated species were almost solvent independent. On the other hand, the absorption maxima and the rates of thermal cis-to-trans isomerization in a given solvent were correlated with Hammett constants. These results are discussed with the help of semi- empirical molecular-orbital calculations and compared with previously published data on related compounds.