787-77-9

Basic information

• Product Name: 2,2'-Dimethoxyhydrazobenzene
• Synonyms: 2,2'-Dimethoxyhydrazobenzene
• CAS NO: 787-77-9
• Molecular Formula: C₁₄H₁₆N₂O₂
• Molecular Weight: 244.289
• Mol File: 787-77-9.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 309°Cat760mmHg
• Flash Point: 130.7°C
• Appearance: /
• Density: 1.196g/cm³
• Vapor Pressure: 0.000658mmHg at 25°C
• Refractive Index: 1.642
• CAS DataBase Reference: 2,2'-Dimethoxyhydrazobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2'-Dimethoxyhydrazobenzene(787-77-9)
• EPA Substance Registry System: 2,2'-Dimethoxyhydrazobenzene(787-77-9)

Safety Data

• Hazardous Substances Data: 787-77-9(Hazardous Substances Data)

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

• 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 
• 91-23-6 2-Nitroanisole 
• 88-73-3 2-Chloronitrobenzene 
• 71-43-2 benzene 

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 
• 119-90-4 3,3'-dimethoxy-(1,1'-biphenyl)-4,4'-diamine 
• 613-55-8 2,2'-dimethoxyazobenzene 
• 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 articles and documents

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.

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.

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.