628-36-4

Basic information

• Product Name: 1,2-Diformylhydrazine
• Synonyms: 1,2-DIFORMYLHYDRAZINE;DIFORMYLHYDRAZINE;Syndiformylhydrazine;N-Formamidoformamide;1,2-Hydrazinedicarbaldehyde;N,N'-Bi(formamide);sym-Diformylhydrazine,97%;1,2-Diformyhydrazine
• CAS NO: 628-36-4
• Molecular Formula: C₂H₄N₂O₂
• Molecular Weight: 88.07
• EINECS: 211-040-5
• Product Categories: Carbonyl Compounds;Hydrazides;Organic Building Blocks;Aromatic Hydrazides, Hydrazines, Hydrazones and Oximes
• Mol File: 628-36-4.mol
• Article Data: 8

Chemical Properties

• Melting Point: 155-157 °C(lit.)
• Boiling Point: 162.99°C (rough estimate)
• Flash Point: 81.6 ºC
• Appearance: White to almost white/Fine Crystalline Powder
• Density: 1.4371 (rough estimate)
• Vapor Pressure: 3.28mmHg at 25°C
• Refractive Index: 1.4264 (estimate)
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Solubility: DMSO (Slightly), Methanol (Slightly, Heated)
• PKA: 11.92±0.23(Predicted)
• CAS DataBase Reference: 1,2-Diformylhydrazine(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Diformylhydrazine(628-36-4)
• EPA Substance Registry System: 1,2-Diformylhydrazine(628-36-4)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• RTECS: LQ8625000
• Hazardous Substances Data: 628-36-4(Hazardous Substances Data)

Usage

Description

1,2-Diformylhydrazine is an organic compound that serves as a bidentate ligand, capable of forming 1:1 metal to ligand complexes with various transition metals such as manganese (Mn), zinc (Zn), and nickel (Ni). It is known for its ability to combine with iron (II) and iron (III) in alkaline conditions, resulting in a complex with an intense red-purple color. This characteristic makes it a valuable reagent in spectrophotometric analysis for the determination of iron (II) and iron (III) ions. However, it is important to note that 1,2-Diformylhydrazine has been observed to increase the likelihood of lung tumor development in mice when administered as a 2% solution.

Uses

Used in Chemical Analysis:
1,2-Diformylhydrazine is used as a reagent in spectrophotometric analysis for the detection and quantification of iron (II) and iron (III) ions. Its ability to form a red-purple complex with these ions in alkaline conditions allows for accurate and sensitive measurements in various applications.
Used in Chemical Synthesis:
As a bidentate ligand, 1,2-Diformylhydrazine is used in the formation of 1:1 metal to ligand complexes with transition metals such as manganese (Mn), zinc (Zn), and nickel (Ni). These complexes have potential applications in various fields, including catalysis, materials science, and coordination chemistry.
It is important to consider the potential health risks associated with 1,2-Diformylhydrazine, as it has been observed to increase the likelihood of lung tumor development in mice when administered as a 2% solution. Proper safety precautions and handling procedures should be followed when working with this compound to minimize exposure and potential health hazards.

InChI:InChI=1/C2H4N2O2/c5-1-3-4-2-6/h1-2H,(H,3,5)(H,4,6)

Upstream product

• 64-18-6 formic acid 
• 141-53-7 sodium formate 
• 122-51-0 orthoformic acid triethyl ester 
• 624-84-0 formic acid hydrazide 
• 77287-34-4 formamide 
• 302-01-2 hydrazine 
• 7803-57-8 hydrazine hydrate 
• 209797-65-9 Formic acid [2-(4-chloro-phenyl)-1-ethoxy-eth-(E)-ylidene]-hydrazide 
• 209797-63-7 Formic acid [1-ethoxy-2-phenyl-eth-(E)-ylidene]-hydrazide 
• 209797-67-1 ethyl p-methylbenzoateformylhydrazone 
• 209797-66-0 Formic acid [1-ethoxy-1-phenyl-meth-(E)-ylidene]-hydrazide 
• 209797-62-6 Formic acid [1-ethoxy-eth-(E)-ylidene]-hydrazide 
• 109-94-4 formic acid ethyl ester 

Downstream Products

• 80535-18-8 4-(4-methylphenyl)-4H-1,2,4-triazole 
• 16227-12-6 1-phenyl-1,3,4-triazole 
• 57058-01-2 1-(4-bromophenyl)-1H-tetrazole 
• 64-18-6 formic acid 
• 7732-18-5 water 
• 917242-54-7 4-(4-ferrocenylphenyl)-4H-[1,2,4]triazole 
• 16227-06-8 {N'-[(dimethylamino)methylene]-N,N-dimethylhydrazonoformamide dihydrochloride} 
• 157069-48-2 4-(4’-carboxyphenyl)-1,2,4-triazole 
• 16120-71-1 1-Formyl-1-benzyl-hydrazin 
• 91333-18-5 6-(4-Aethoxy-anilino)-4-amino-1.3.5-triazin 
• 90564-70-8 4-o-tolyl-1,2,4-triazole 
• 99989-86-3 4-(5-methyl-2-phenyl-2H-pyrazol-3-yl)-4H-[1,2,4]triazole 
• 787-84-8 N'-benzoylbenzohydrazide 
• 584-13-4 4-amino-1,2,4-triazole 

Relevant articles and documents

Synthesis, Structure, and Characterization of 3, 4′-Bis-1H-1, 2,4-triazolium Picrate Salt: A New High-Energy Density Material

The environmentally friendly high-energy density salt (TRTR)(PA) (TRTR = 3, 4′-bis-1, 2,4-1H-triazole, PA = 2, 4,6-trinitrophenol, picric acid) was synthesized and characterized. The X-ray single crystal diffraction results illustrate that the structure of title salt belongs to the monoclinic system, space group P21/c. Many parallel relationships exist in the molecule, as well as a strong intramolecular π-π stacking interaction. The DSC result shows only one exothermal decomposition step at 229.1 C. The TG-DTG curve demonstrates a 75.9 % mass loss from 180 C to 300 C at a rate of 3.01 %·K-1. Experimental data show that the combustion heat approximately equals to TNT (-15.22 MJ·kg-1) and the enthalpy of formation is +332.2 kJ·mol-1. Non-isothermal kinetic and thermodynamic parameters were obtained by two methods (Kissinger and Ozawa). Detonation pressure and velocity were calculated to be 23.4 GPa and 7.32 km·s-1, respectively. Additionally, the sensitivities towards impact and friction were assessed with relevant standard methods.

Synthesis and molecular properties of formic hydrazides

The existence of 1,3-silatropic transformation in N',N'-dimethyl-N-(trimethylsilyl)formic hydrazide was discovered. In the crystal, its molecules form chains due to bifurcated hydrogen bonds.

Synthesis and characterization of two formyl 2-tetrazenes

The synthesis of two formyl 2-tetrazenes, namely, (E)-1-formyl-1,4,4- trimethyl-2-tetrazene (2) and (E)-1,4-diformyl-1,4-dimethyl-2-tetrazene (3), by oxidation of (E)-1,1,4,4-tetramethyl-2-tetrazene (1) using potassium permanganate in acetone solution is presented. Compound 3 was also synthesized in an improved yield from the oxidation of 1-formyl-1-methylhydrazine (4 a) using potassium permanganate in acetone. Both compounds 2 and 3 were characterized by analytical (elemental analysis, GC-MS) and spectroscopic methods (1H, 13C, and 15N NMR spectroscopy, and IR and Raman spectroscopy). In addition, the solid-state structures of the compounds were confirmed by low-temperature X-ray analysis. (Compound 2: triclinic; space group P-1; a=5.997(1) A, b=8.714(1) A, c=13.830(2) A; α=107.35(1)°, β=90.53(1)°, γ=103.33(1)°; VUC=668.9(2) A3; Z=4; ρcalc=1.292 cm-3. Compound 3: monoclinic; space group P21/c; a=5.840(2) A, b=7.414(3) A, c=8.061(2) A; β=100.75(3) °; VUC=342(2) A3; Z=2; ρcalc=1. 396 g cm-3.) The vibrational frequencies of compounds 2 and 3 were calculated using the B3LYP method with a 6-311+G(d,p) basis set. We also computed the natural bond orbital (NBO) charges using the rMP2/aug-cc-pVDZ method and the heats of formation were determined on the basis of their electronic energies. Furthermore, the thermal stabilities of these compounds, as well as their sensitivity towards classical stimuli, were also assessed by differential scanning calorimetry and standard BAM tests, respectively. Lastly, the attempted synthesis of (E)-1,2,3,4-tetraformyl-2-tetrazene (6) is also discussed.