787-77-9

Usage

InChI:InChI=1/C14H16N2O2/c1-17-13-9-5-3-7-11(13)15-16-12-8-4-6-10-14(12)18-2/h3-10,15-16H,1-2H3

Upstream product

• 91-23-6 2-Nitroanisole 
• 13620-57-0 2,2'-dimethoxyazoxybenzene 
• 67-56-1 methanol 
• 613-55-8 2,2'-dimethoxyazobenzene 
• 19129-74-9 trans-2,2'-dimethoxyazobenzene 
• 50-99-7 D-glucose 
• 71-43-2 benzene 
• 88-73-3 2-Chloronitrobenzene 

Downstream Products

• 137182-62-8 4-acetyl-1,2-dihydro-1,2-bis(2-methoxyphenyl)-5-methyl-3H-pyrazol-3-one 
• 55908-57-1 1,2-dihydro-1,2-bis(2-methoxyphenyl)-5-methyl-3H-pyrazol-3-one 
• 613-55-8 2,2'-dimethoxyazobenzene 
• 119-90-4 3,3'-dimethoxy-(1,1'-biphenyl)-4,4'-diamine 
• 13620-57-0 2,2'-dimethoxyazoxybenzene 
• 19129-74-9 trans-2,2'-dimethoxyazobenzene 
• 102318-36-5 benzoic acid-(2-o-anisidino-6-methoxy-anilide) 
• 13620-57-0 (Z)-1,2-bis(2-methoxyphenyl)diazene 1-oxide 

Relevant academic research and scientific papers

O-Anisidine Dimer, 2-Methoxy- N4-(2-methoxyphenyl) Benzene-1,4-diamine, in Rat Urine Associated with Urinary bladder Carcinogenesis

Monocyclic aromatic amines, o-toluidine (o-Tol) and its structural analog o-anisidine (o-Ans), are IARC Group 1 and Group 2A urinary bladder carcinogens, respectively, and are involved in metabolic activation and DNA damage. Our recent study revealed that 2-methyl-N4-(2-methylphenyl) benzene-1,4-diamine (MMBD), a p-semidine-type homodimer of o-Tol, was detected and identified in an in vitro reaction of o-Tol with S9 mix and in vivo urinary samples of o-Tol-exposed rats. Potent mutagenic, genotoxic, and cytotoxic activities were reported with MMBD, suggesting its involvement in urinary bladder carcinogenesis. However, it remains unknown whether o-Ans is converted to active metabolites to induce DNA damage in a similar manner as o-Tol. In this study, we report that a novel o-Ans metabolite, 2-methoxy-N4-(2-methoxyphenyl) benzene-1,4-diamine (MxMxBD), a dimer by head-to-tail binding (p-semidine form), was for the first time identified in o-Ans-exposed rat urine. MxMxBD induced a stronger mutagenicity in N-acetyltransferase overexpressed Salmonella typhimurium strains and potent genotoxicity and cytotoxicity in human bladder carcinoma T24 cells compared with o-Ans. These results suggest that MxMxBD may to some extent contribute toward urinary bladder carcinogenesis. In addition to homodimerization, such as MxMxBD, heterodimerizations were observed when o-Ans was coincubated with o-Tol or aniline (Ani) in in vitro reactions with S9 mix. This study highlights the important consideration of homodimerizations and heterodimerizations of monocyclic aromatic amines, including o-Ans, o-Tol, and Ani, in the evaluation of the combined exposure risk of bladder carcinogenesis.

Tandem selective reduction of nitroarenes catalyzed by palladium nanoclusters

We report a catalytic tandem reduction of nitroarenes by sodium borohydride (NaBH4) in aqueous solution under ambient conditions, which can selectively produce five categories of nitrogen-containing compounds: anilines, N-aryl hydroxylamines, azoxy-, azo- and hydrazo-compounds. The catalyst is in situ-generated ultrasmall palladium nanoclusters (Pd NCs, diameter of 1.3 ± 0.3 nm) from the reduction of Pd(OAc)2 by NaBH4. These highly active Pd NCs are stabilized by surface-coordinated nitroarenes, which inhibit the further growth and aggregation of Pd NCs. By controlling the concentration of Pd(OAc)2 (0.1-0.5 mol% of nitroarene) and NaBH4, the water/ethanol solvent ratio and the tandem reaction sequence, each of the five categories of N-containing compounds can be obtained with excellent yields (up to 98%) in less than 30 min at room temperature. This tunable catalytic tandem reaction works efficiently with a broad range of nitroarene substrates and offers a green and sustainable method for the rapid and large-scale production of valuable N-containing chemicals.

Synthetic method for 4,4'-dihalogenated-3,3'-dialkyl(alkoxyl) biphenyl compounds

The invention relates to a synthetic method for 4,4'-dihalogenated-3,3'-dialkyl(alkoxyl) biphenyl compounds. The method employs o-nitro alkyl (alkoxyl) benzene as an initial raw material, 2,2'-dialkyl(alkoxyl) hydrazobenzene is prepared through catalysis hydrogenation in an alkaline environment, hydrochloric acid acidifying rearrangement is carried out, 4,4'-diamino-3,3'-dialkyl(alkoxyl) biphenyl is prepared, finally, a diazotization reaction is carried out and 4,4'-dihalogenated-3,3'-dialkyl(alkoxyl) biphenyl compounds are prepared. The synthetic method is advantaged by cheap and easily available raw materials, mild reaction conditions, simple operation, high safety coefficient, high yield and low cost.

Mg/Triethylammonium formate: A useful system for reductive dimerization of araldehydes into pinacols; Nitroarenes into azoarenes and azoarenes into hydrazoarenes

Studies are reported which describes the effectiveness of triethylammonium formate in the presence of magnesium for the efficient intermolecular pinacol coupling using MeOH as solvent, Various aromatic carbonyls underwent smooth reductive coupling to give the corresponding I ,2-diols. A series of azo compounds were obtained by the reductive coupling of nitroaromatics while azo compounds were reduced to the corresponding hydrazoarenes by this system. There was no adverse effect on the other reducible and hydrogenolysable groups such as ether linkage, hydroxy and halogens. The reactions are clean, high yielding and inexpensive. All the reactions proceeded smoothly at ambient temperature.

Conversion of azobenzenes into N,N′-diarylhydrazines by sodium dithionite

A number of chloro-, methyl- and methoxy-substituted azobenzenes have been reduced to the corresponding hydrazines by using an aqueous solution of Na 2S2O4. The yield is generally excellent, but two compounds, viz. 4,4-dimethoxyazobenzene and 2,2,4,4,6,6- hexamethylazobenzene, gave no hydrazine at all. Georg Thieme Verlag Stuttgart.

An efficient and product selective reduction of azoxyarenes into azoarenes or hydrazoarenes by tin/hydrazine hydrate

A general and rapid method is described for the reduction of azoxyarenes to give the corresponding hydrazoarenes under microwave irradiation and azoarenes at reflux conditions on treatment with hydrazine hydrate in the presence of tin metal in methanol. The reactions are found to be fast and clean, give excellent yield and high purity of the products. Ether linkage and Cl are unaffected.

Facile, product-selective reduction of azoxyarenes into azoarenes or hydrazoarenes by aluminium/hydrazine hydrate

Azoxyarenes, on treatment with hydrazine hydrate in presence of aluminium powder in methanol, undergo reduction. The reactions have been carried under microwave irradiation as well at reflux to get the corresponding hydrazoarenes and azoarenes as reduced products. The reaction is very fast, which gives excellent yield of the product. Substituents such as OCH3, OC 2H5, and Cl are unaffected. Copyright Taylor & Francis, Inc.

A facile reduction of azoxyarenes with hydrazine hydrate/magnesium: Formation of different products under different reaction conditions

Azoxyarenes on treatment with hydrazine hydrate in presence of magnesium turnings in methanol undergo reduction. The reactions have been carried under microwave irradiation as well as at reflux to give the corresponding hydrazoarenes and azoarenes as reduced products. The reactions are very fast and give excellent yields of the products. Substituents like OCH3, OC2H5 and Cl are unaffected.

Facile Transfer Hydrogenation of Azo Compounds to Hydrazo Compounds and Anilines by Using Raney Nickel and Hydrazinium Monoformate

Azo compounds are conveniently reduced to either partially reduced hydrazo compounds or completely reduced anilines by employing Raney nickel in presence of hydrazinium monoformate depending upon reaction conditions. The other reducible moieties like -COOH and halogens are tolerated. The reduction process is selective, rapid and high yielding.

Pyridazinedione derivatives useful in treatment of neurological disorders

The present invention relates to pyridazino[4,5-b]indoles, and pharmaceutically useful salts thereof, which are excitatory amino acid antagonists and which are useful when such antagonism is desired such as in the treatment of neurological disorders. The invention further provides pharmaceutical compositions containing pyridazino[4,5-b]indoles as active ingredient, and methods for the treatment of neurological disorders.