1567-91-5

Basic information

• Product Name: (1E)-bis(3-nitrobenzylidene)hydrazine
• Synonyms: (1E)-Bis(3-nitrobenzylidene)hydrazine
• CAS NO: 1567-91-5
• Molecular Formula: C₁₄H₁₀N₄O₄
• Molecular Weight: 298.2536
• Mol File: 1567-91-5.mol

Chemical Properties

• Boiling Point: 456.969°C at 760 mmHg
• Flash Point: 230.167°C
• Density: 1.349g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.637
• CAS DataBase Reference: (1E)-bis(3-nitrobenzylidene)hydrazine(CAS DataBase Reference)
• NIST Chemistry Reference: (1E)-bis(3-nitrobenzylidene)hydrazine(1567-91-5)
• EPA Substance Registry System: (1E)-bis(3-nitrobenzylidene)hydrazine(1567-91-5)

Safety Data

• Hazardous Substances Data: 1567-91-5(Hazardous Substances Data)

Usage

Uses

Used in Coordination Chemistry:
(1E)-bis(3-nitrobenzylidene)hydrazine is used as a ligand in coordination chemistry for its ability to form stable metal complexes. This application is crucial for the development of new materials with potential applications in various fields, such as catalysis, sensing, and medicine.
Used in Medicinal Chemistry:
(1E)-bis(3-nitrobenzylidene)hydrazine is used as a precursor for the synthesis of metal complexes with potential biological activity. Its exploration as an anticancer agent highlights the importance of understanding its interactions with biological systems and the possibility of developing it into a therapeutic agent for cancer treatment.
Further research is necessary to fully understand and harness the potential applications of (1E)-bis(3-nitrobenzylidene)hydrazine, particularly in the areas of coordination chemistry and medicinal chemistry, where it may contribute to the advancement of new technologies and treatments.

Upstream product

• 3718-22-7 3-nitrobenzaldehyde hydrazone 
• 99-61-6 3-nitro-benzaldehyde 
• 3378-51-6 N-(3-Nitro-benzyliden)-4-rhodan-anilin 
• 64-17-5 ethanol 
• 7783-06-4 hydrogen sulfide 
• 137-26-8 Thiram 
• 354-58-5 1,1,1-Trichloro-2,2,2-trifluoroethane 
• 76-13-1 1,1,2-Trichloro-1,2,2-trifluoroethane 
• 75-61-6 dibromodifluoromethane 
• 124-73-2 1,2-dibromo-1,1,2,2-tetrafluoroethane 
• 5706-76-3 2-(3-nitrobenzylidene)hydrazinecarbothioamide 
• 5346-31-6 3-nitro-benzaldehyde semicarbazone 
• 3748-99-0 N'-(3-nitrobenzylidene)-4-methylbenzenesulfonohydrazide 

Downstream Products

• 873987-69-0 3-nitro-N'-(3-nitro-benzylidene)-benzohydrazonoyl chloride 
• 1709-44-0 m-aminobenzaldehyde 
• 5346-31-6 3-nitro-benzaldehyde semicarbazone 
• 99-61-6 3-nitro-benzaldehyde 
• 21388-97-6 3-nitrobenzyl acetate 
• 121-92-6 3-nitrobenzoic acid 
• 21881-77-6 m-nifedipine 
• 873987-53-2 3-nitro-N'-(3-nitro-benzylidene)-benzohydrazonoyl azide 
• 1259883-45-8 diethyl (3-nitrobenzylidenehydrazino)(3-nitrophenyl)methylphosphonate 
• 1259883-49-2 tetraethyl α,α'-hydrazobis(3-nitrobenzylphosphonate) 

Relevant articles and documents

Unusual synthesis of azines and their oxidative degradation to carboxylic acid using iodobenzene diacetate

Reaction of 3-hydrazonobutan-2-one oxime with aromatic aldehydes resulted in the formation of 1,2-bis(arylidene)hydrazine commonly referred as azine as an unexpected product, instead of expected product 3-(aryl)methylenehydrazonobutan-2-one oxime, which were subsequently oxidized to corresponding aromatic acids with an ecofriendly oxidizing agent iodobenzene diacetate. Azines and carboxylic acids were characterized by IR and NMR (1H, 13C, HMBC, and HMQC) studies.

Cs2CO3-mediated decomposition of N-tosylhydrazones for the synthesis of azines under mild conditions

Abstract: A facile, environmentally and efficient Cs2CO3-mediated decomposition of N-tosylhydrazones reaction has been developed for the synthesis of functionalized azines under mild conditions. This method offers broad substrate scope, occurs as additive-free, without strong base conditions, utilizes readily available reactants, and forms products in good to high yields. Graphical Abstract: [Figure not available: see fulltext.]

An efficient synthesis of perhydro[1,2,4]triazolo[1,2-a][1,2,4]triazole-1,5-dithiones catalyzed by TiO2-functionalized nano-Fe3O4 encapsulated-silica particles as a reusable magnetic nanocatalyst

Immobilization of a nano-TiO2 catalyst on the surface of a magnetic SiO2 support was performed through the reaction of a Fe3O4@SiO2 composite with Ti(OC4H9)4via a simple process. The Fe3O4@SiO2-TiO2 nanocomposite was characterized using scanning electron microscopy (SEM), transmission electron microscopy (TEM), energy dispersive X-ray spectroscopy (EDS), X-ray diffraction (XRD), Fourier transform infrared spectra (FTIR), and a vibrating sample magnetometer (VSM). The Fe3O4@SiO2-TiO2 nanocomposite has been found to be an efficient catalyst for the synthesis of perhydro[1,2,4]triazolo[1,2-a][1,2,4]triazole-1,5-dithiones from the condensation of various aldazines and potassium thiocyanate in acetonitrile solvent at room temperature. It has been found that the nanocatalyst was recycled for up to 6 cycles with minimal loss in catalytic activity. The purpose of this research was to provide an easy method for the synthesis of perhydrotriazolotriazole derivatives by a robust and magnetically recoverable catalyst.

An expeditious synthetic approach towards the synthesis of Bis-Schiff bases (aldazines) using ultrasound

Aldazines (Bis-Schiff bases) 1-24 were synthesized using aromatic aldehydes (heterocyclic and benzaldehydes) and hydrazine hydrate under reflux using conventional heating and/or via ultrasound irradiation using BiCl3 as catalyst. Ultrasonication conditions with cat. BiCl3 proved to be an effective, environmentally friendly synthetic procedure. This methodology is robust in the presence of electron donating and electron withdrawing groups affording desired products with high yields (>95%) in just a couple of minutes vs. hours using conventional heating.

Microwave-assisted synthesis of 1-hydrazinophosphonates via the reaction of aldazines with dialkyl phosphite

A simple, efficient, and novel method has been developed for the synthesis of 1-hydrazinophosphonic acids from aldazines. As described below, treatment of aldazines with diethyl phosphite gives the corresponding 1-hydrazinophosphonic acids in good yields. The reaction proceeds under microwave irradiation at 110°C and neutral condition without any additives such as base, acid, or catalyst. This method is easy, rapid, and gives good yields for the 1-hydrazinophosphonic acids.

Facile method for the conversion of semicarbazones/thiosemicarbazones into azines (Under Microwave Irradiation) and oxadiazoles (By Grinding)

In an effective transformation, semicarbazones/thiosemicarbazones are smoothly converted into azines under microwave irradition. Oxadiazoles are also obtained from semicarbazones by reaction with bromine generated in situ via a grinding reaction in the solid phase. Taylor &Francis Group, LLC.

Synthesis of azines in solid state: Reactivity of solid hydrazine with aldehydes and ketones

Highly conjugated azines were prepared by solid state grinding of solid hydrazine and carbonyl compounds such as aldehydes and ketones, using a mortar and a pestle. Complete conversion to the azine product is generally achieved at room temperature within 24 h, without using solvents or additives. The solid-state reactions afford azines as the sole products with greater than 97% yield, producing only water and carbon dioxide as waste.

Selective and convenient protection of aldehydes as azines under solvent-free conditions

Aldehydes can be easily protected as azines in the presence of hydrazine monohydrochloride and ferric chloride under solvent-free conditions. The major advantages of this method are: operational simplicity, ready availability, selectivity, general applicability, mild reaction conditions with low cost of the reactants, short reaction times and excellent yields.

Reaction of CBrF2-CBrF2 with hydrazones of aromatic aldehydes. Novel efficient synthesis of fluorocontaining alkanes, alkenes and alkynes

An olefination of hydrazones of aromatic aldehydes by CBrF2-CBrF2 under copper catalysis was investigated. In situ prepared aldehydes hydrazones were converted to (3-bromo-2,2,3,3-tetrafluoropropyl)arenes by reaction with CBrF2-CBrF2 in the presence of CuCl. Subsequent elimination of HF by sodium hydroxide resulted in stereospecific formation of fluorocontaining alkenes. Elimination proceeds stereoselectively, only Z -isomers of alkenes are formed. Elimination of two molecules of HF from (3-bromo-2,2,3,3-tetrafluoropropyl)arenes by treatment with potassium tert -butoxide leads to formation of (bromodifluoromethyl)alkynes. As a result a simple and efficient transformation of aromatic aldehydes to range of various fluorinated alkanes, alkenes and alkynes was elaborated.

A novel direct synthesis of (2,2-difluorovinyl)benzenes from aromatic aldehydes

A novel catalytic approach to (2,2-difluorovinyl)benzenes has been developed. It was found that hydrazones of aromatic aldehydes generated in situ could be converted to the corresponding (2,2-difluorovinyl)benzenes by catalytic olefination reaction (COR) with dibromodifluoromethane in the presence of CuCl.