71082-02-5

Basic information

• Product Name: N,N'-bis-(p.hyroxyphenyl)-2-hydroxy-5-amino-1,4-benzoquinone
• Synonyms: N,N'-bis-(p.hyroxyphenyl)-2-hydroxy-5-amino-1,4-benzoquinone
• CAS NO: 71082-02-5
• Molecular Weight: 321.335
• Mol File: 71082-02-5.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: N,N'-bis-(p.hyroxyphenyl)-2-hydroxy-5-amino-1,4-benzoquinone(CAS DataBase Reference)
• NIST Chemistry Reference: N,N'-bis-(p.hyroxyphenyl)-2-hydroxy-5-amino-1,4-benzoquinone(71082-02-5)
• EPA Substance Registry System: N,N'-bis-(p.hyroxyphenyl)-2-hydroxy-5-amino-1,4-benzoquinone(71082-02-5)

Safety Data

• Hazardous Substances Data: 71082-02-5(Hazardous Substances Data)

Upstream product

• 637-61-6 benzoquinone N-chloroimine 
• 123-30-8 4-amino-phenol 

Relevant articles and documents

Cyclodextrin-based artificial oxidases with high rate accelerations and selectivity

Three cyclodextrin derivatives with one to four 2-O-formylmethyl groups attached to the secondary rim were prepared and investigated as catalysts for the oxidation of aminophenols in buffered dilute hydrogen peroxide. The derivatives were found to be Michaelis-Menten catalysts and to give rate accelerations of up to 20,000 for the oxidation of 2-aminophenol to 2-amino-phenoxazin-3-one, and 12,000 for the oxidation of 2-amino-p-cresol to 2-nitro-p-cresol. While a range of differently substituted substrates was oxidized the success of the reaction was highly dependent on the substituent pattern. The ability of one of the new artificial enzymes to oxidize selectively one aminophenol from a mixture of two was investigated giving substrate selectivities of up to 16:1.

Simple cyclodextrin aldehydes as excellent artificial oxidases

Cyclodextrin based oxidases, with a ketone as functional group are well known as good artificial enzyme mimics (Fenger et al. Org Biomol Chem 7:933-943; Marinescu and Bols Angew Chem Int Ed 45:4590-4593; Bjerre et al. Eur J Org Chem 704-710; Marinescu et al. J Am Chem Soc 127:17578-17579). We here report a series of modified cyclodextrins, having aldehydes as functional groups. The aldehyde based artificial enzymes have, in most cases, better catalysis than the ketones, because of their powerful covalent binding of hydrogen peroxide. Among the modified cyclodextrins studied are mono and di aldehydes on the 6 positions, with or without methylated hydroxyl groups. The aldehyde functionality was also introduced close to the secondary side, by attaching ethoxy-2-al or propoxy-3-al to the 2 position. The modified cyclodextrins showed excellent enzymatic activity towards oxidation of different aminophenols, and 4-methoxy benzyl alcohol with hydrogen peroxide as a stoichiometric oxidant. Rate enhancements up to 4,600 were achieved for oxidation of 4-methoxy benzyl alcohol, where as oxidation of amines gave rate enhancements up to 3,400. The artificial oxidases catalyses oxidations under enzymatic conditions (water, pH 7, 25 °C), following Michaelis-Menten kinetics. To confirm the enzyme activity, inhibition studies with sodium naphthalene-2-sulfonate were carried out. These studies showed competitive inhibition of the enzymes, verifying the cyclodextrins enzyme like character.

MECANISMES DE REDUCTION ELECTROCHIMIQUE DES QUINONES MONO ET DICHLORIMINE SUR PLATINE. ETUDE ET STRUCTURE DES COMPOSES OBTENUS LORS DE COULOMETRIES A FORTE CONCENTRATION

In this work, electrochemical reduction of quinone mono and dichlorimine was investigated on platinum cathodes.The first product produces paraaminophenol and the second produces paraphenylenediamine.Chemical reactions occur when the concentration of initial product is higher than E-4 M.Reaction between quinone monochlorimine and its ultimate reduction product occurs when concentrated solution are electrolysed on a platinum cathode.In this work, the nature and the structure of the reaction products were eluciated by physicochemical methods.An approach of the reaction mechanism is proposed.