4377-76-8

Upstream product

• 95-55-6 2-amino-phenol 
• 24541-44-4 2-azidophenol 

Downstream Products

• 1916-59-2 2-aminophenoxazin-3-one 

Relevant academic research and scientific papers

Matrix isolation of o-quinoid compounds - 6-imino-2,4-cyclohexadien-1-one and 1,2-diimino-3,5-cyclohexadiene

6-Imino-2,4-cyclohexadien-1-one (1b) and 1,2-diimino-3,5-cyclohexadiene (1c) were generated in high yields from o-azidophenol (5b) and o-azidoaniline (5c), respectively, by irradiation in argon matrices at 10 K or by flash vacuum pyrolysis (FVP) with subsequent trapping of the products in solid argon. The hydrogen shift in the phenylnitrenes 6 formed as primary intermediates is very rapid, and thus the nitrenes are short-lived transients even under the conditions of matrix isolation. Ring expansion to azacycloheptatetraenes was not observed. FVP produces the thermodynamically most stable E/Z isomers of the quinones as the main products. Photolysis of the matrix-isolated quinones results in photostationary equilibria of the E/Z isomers. The stereoisomers were identified by comparison of the matrix IR spectra with ab initio calculations at the RMP2-FC-6/31G(d) level of theory. VCH Verlagsgesellschaft mbH, 1996.

Tris(2,2′-azobispyridine) complexes of copper(II): X-ray structures, reactivities, and the radical nonradical bis(ligand) analogues

Tris(abpy) complexes of types mer-[CuII(abpy)3][PF6]2 (mer-12+[PF6-]2) and ctc-[CuII(abpy)2(bpy)][PF6]2 (ctc-22+[PF6-]2) were successfully isolated and characterized by spectra and single-crystal X-ray structure determinations (abpy = 2,2′-azobispyridine; bpy = 2,2′-bipyridine). Reactions of mer-12+ and ctc-22+ ions with catechol, o-aminophenol, p-phenylenediamine, and diphenylamine (Ph-NH-Ph) in 2:1 molar ratio afford [CuI(abpy)2]+ (3+) and corresponding quinone derivatives. The similar reactions of [CuII(bpy)3]2+ and [CuII(phen)3]2+ with these substrates yielding [CuI(bpy)2]+ and [CuI(phen)2]+ imply that these complexes undergo reduction-induced ligand dissociation reactions (phen = 1,10-phenanthroline). The average -N=N- lengths in mer-12+[PF6-]2 and ctc-22+[PF6-]2 are 1.248(4), while that in 3+[PF6-]·2CH2Cl2 is relatively longer, 1.275(2) ?, due to dCu → πazo back bonding. In cyclic voltammetry, mer-12+ exhibits one quasi-reversible wave at -0.42 V due to CuII/CuI and abpy/abpy?- couples and two reversible waves at -0.90 and -1.28 V due to abpy/abpy?- couple, while those of ctc-22+ ion appear at -0.44, -0.86, and -1.10 V versus Fc+/Fc couple. The anodic 32+/3+ and the cathodic 3+/3 redox waves at +0.33 and -0.40 V are reversible. The electron paramagnetic resonance spectra and density functional theory (DFT) calculations authenticated the existence of abpy anion radical (abpy?-) in 3, which is defined as a hybrid state of [CuI(abpy0.5?-)(abpy0.5?-)] and [CuII(abpy?-)(abpy?-)] states. 32+ ion is a neutral abpy complex of copper(II) of type [CuII(abpy)2]2+. 3 exhibits a near-IR absorption band at 2400-3000 nm because of the intervalence ligand-to-ligand charge transfer, elucidated by time-dependent DFT calculations in CH2Cl2.

Kinetic characterisation of o-aminophenols and aromatic o-diamines as suicide substrates of tyrosinase

We study the suicide inactivation of tyrosinase acting on o-aminophenols and aromatic o-diamines and compare the results with those obtained for the corresponding o-diphenols. The catalytic constants follow the order aromatic o-diamines max/KmS, follows this order: o-diphenols > o-aminophenols > aromatic o-diamines.

Effect of the structure of amines on the rate constants of their reactions with diphenylcarbonyl oxide

Flash photolysis and fast-response spectrophotometry were used to measure the rate constants for the reactions of diphenylcarbonyl oxide Ph2COO with aliphatic and aromatic amines. The reactivity of the amines studied increase in the following s

Photochemistry of phenyl azides bearing 2-hydroxy and 2-amino groups studied by matrix-isolation spectroscopy: Generation and characterization of reactive o-quinoid compounds

Broad-band irradiation (λ > 370 nm) of 2-hydroxyphenyl azide (1) in Ar at 10 K monitored by IR resulted in the formation of at least three major products, all of which were shown to be photointerconvertible under these conditions. The two products showing

Isophenoxazine Synthase Model. Oxidation of o-Aminophenol by an Oxidation-active Flavin Mimic in an Aqueous Solution

It was found that a flavin mimic, benzo-dipteridine (BDP), oxidizes o-aminophenol in an aqueous solution under anaerobic conditions.Under aerobic conditions, 2-aminophenoxazine-3-one was isolated.This is the first example of an isophenoxazine synthase mod