953-01-5

Usage

Physical state

Clear, colorless to pale yellow liquid

Odor

Slightly sweet

Chemical intermediate

Production of dyes, pharmaceuticals, and other organic compounds
b. Corrosion inhibitor
c. Flame retardant
d. Reagent in organic chemistry reactions

Potential applications

Antitumor agent (cytotoxic effects on certain types of cancer cells)

Hazards

Toxic and potentially hazardous to human health and the environment

Safety precautions

Handle with caution

Upstream product

• 15426-14-9 3,3'-dichloroazobenzene 
• 139-24-2 3,3'-dichloroazoxybenzene 
• 121-73-3 3-Nitrochlorobenzene 
• 106131-20-8 (E)-1,2-bis(3-chlorophenyl)diazene 
• 88-73-3 2-Chloronitrobenzene 
• 75-09-2 dichloromethane 
• 139-24-2 3,3'-dichloroazoxybenzene 

Downstream Products

• 84-68-4 2,2'-dichlorobenzidine 
• 15426-14-9 3,3'-dichloroazobenzene 
• 106943-54-8 1,2-Bis(3-chlorphenyl)-5-cyclohexylamino-1,2-dihydro-4-hydroxy-3H-pyrazol-3-on 
• 55138-13-1 1,2-bis-(3-chloro-phenyl)-pyrazolidine-3,5-dione 
• 2528-73-6 4.4'-Di-(4-heptyloxy-benzylidenamino)-2.2'-dichlor-biphenyl 
• 30930-38-2 1-(3-chlorophenylamino)naphthalen-2-ol 
• 108-42-9 3-chloro-aniline 
• 106131-20-8 (E)-1,2-bis(3-chlorophenyl)diazene 

Relevant academic research and scientific papers

Visible-Light-Promoted Diboron-Mediated Transfer Hydrogenation of Azobenzenes to Hydrazobenzenes

A visible-light-promoted transfer hydrogenation of azobenzenes has been developed. In the presence of B2pin2 and upon visible-light irradiation, the reactions proceeded smoothly in methanol at ambient temperature. The azobenzenes with diverse functional groups have been reduced to the corresponding hydrazobenzenes with a yield of up to 96%. Preliminary mechanistic studies indicated that the hydrogen atom comes from the solvent and the transformation is achieved through a radical pathway.

Synthesis of novel 1,2-diarylpyrazolidin-3-one–based compounds and their evaluation as broad spectrum antibacterial agents

There is a continuous need to develop new antibacterial agents with non-traditional mechanisms to combat the nonstop emerging resistance to most of the antibiotics used in clinical settings. We identified novel pyrazolidinone derivatives as antibacterial hits in an in-house library screening and synthesized several derivatives in order to improve the potency and increase the polarity of the discovered hit compounds. The oxime derivative 24 exhibited promising antibacterial activity against E. coli TolC, B. subtilis and S. aureus with MIC values of 4, 10 and 20 μg/mL, respectively. The new lead compound 24 was found to exhibit a weak dual inhibitory activity against both the E. coli MurA and MurB enzymes with IC50 values of 88.1 and 79.5 μM, respectively, which could partially explain its antibacterial effect. A comparison with the previously reported, structurally related pyrazolidinediones suggested that the oxime functionality at position 4 enhanced the activity against MurA and recovered the activity against the MurB enzyme. Compound 24 can serve as a lead for further development of novel and safe antibiotics with potential broad spectrum activity.

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.

Bidirectional synthesis of the central amino acid of chloptosin

(Chemical Equation Presented) An efficient total synthesis of (2S,2′S,3aR,3′aR,8aR,8′aR)-6,6′-dichloro-3a, 3′a-dihydroxy-1,1′,2,2′,3,3a,3′,3′a,8,8a,8′, 8′a-dodecahydro-5,5′-bipyr-rolo[2,3-b]indole-2,2′- dicarboxylic acid, the central amino acid component of chloptosin (1), is described. Starting from m-chloronitrobenzene, this C2-symmetrical amino acid was synthesized by using a 14-step route, in which a Zinin benzidine rearrangement, intramolecular Heck reaction, and selenocyclization and oxidative deselenation served as key steps. The absolute stereochemistry of the target was confirmed by X-ray single-crystal studies on a key intermediate (17).

Tin-mediated reduction of azoarenes to hydrazoarenes using hydrazine hydrate

The controlled reduction of azoarenes to the corresponding hydrazoarenes using tin and hydrazine hydrate is reported. The reduction proceeds smoothly at room temperature furnishing the hydrazoarene in excellent yield without the formation of an aniline.

Pyrazolidine-3,5-diones and 5-hydroxy-1H-pyrazol-3(2H)-ones, inhibitors of UDP-N-acetylenolpyruvyl glucosamine reductases

A series of pyrazolidine-3,5-dione and 5-hydroxy-1H-pyrazol-3(2H)-one inhibitors of Escherichia coli UDP-N-acetylenolpyruvyl glucosamine reductase (MurB) has been prepared. The 5-hydroxy-1H-pyrazol-3(2H)-ones show low micromolar IC50 values versus E. coli MurB and submicromolar minimal inhibitory concentrations (MIC) against Staphylococcus aureus GC 1131, Enterococcus faecalis GC 2242, Streptococcus pneumoniae GC 1894, and E. coli GC 4560 imp, a strain with increased outer membrane permeability. None of these compounds show antimicrobial activity against Candida albicans, a marker of eukaryotic toxicity. Moreover, these compounds inhibit peptidoglycan biosynthesis, as assessed by measuring the amount of soluble peptidoglycan produced by Streptococcus epidermidis upon incubation with compounds. A partial least squares projection to latent structures analysis shows that improving MurB potency and MIC values correlate with increasing lipophilicity of the C-4 substituent of the 5-hydroxy-1H-pyrazol-3(2H)-one core. Docking studies using FLO and PharmDock produced several binding orientations for these molecules in the MurB active site.

Ammonium chloride mediated reduction of azo compounds to hydrazo compounds

The reduction of azo compounds with magnesium powder as catalyst in the presence of ammonium chloride at room temperature in methanol leads to hydrazo compounds.

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.

Process for the preparation of benzene compounds

The reduction of azoxybenzene, azobenzenes and mixtures of azoxybenzenes and azobenzene to the hydrazobenzenes is possible under mild conditions, with high yields and without any great excess of reducing agents in the presence of raney-nickel and compounds which have an alkaline action with hydrogen or hydrazine hydrate.