22719-28-4

Basic information

• Product Name: 1,2-bis(4-nitrophenyl)hydrazine
• Synonyms: 1,2-Bis(4-nitrophenyl)hydrazine; 4,4'-Dinitrohydrazobenzene; hydrazine, 1,2-bis(4-nitrophenyl)-
• CAS NO: 22719-28-4
• Molecular Formula: C₁₂H₁₀N₄O₄
• Molecular Weight: 274.2322
• Mol File: 22719-28-4.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 388.8°C at 760 mmHg
• Flash Point: 189°C
• Density: 1.524g/cm³
• Vapor Pressure: 2.97E-06mmHg at 25°C
• Refractive Index: 1.752
• CAS DataBase Reference: 1,2-bis(4-nitrophenyl)hydrazine(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-bis(4-nitrophenyl)hydrazine(22719-28-4)
• EPA Substance Registry System: 1,2-bis(4-nitrophenyl)hydrazine(22719-28-4)

Safety Data

• Hazardous Substances Data: 22719-28-4(Hazardous Substances Data)

Usage

Appearance

Yellow crystalline solid

Usage

a. Reagent for detection of aldehydes and ketones
b. Synthesis of pharmaceuticals
c. Synthesis of dyes
d. Synthesis of other organic compounds

Toxicity

Handle with care due to its toxic nature

Potentially explosive

Under certain conditions, it can be explosive

Banned use

Weight loss products (due to potential health risks)

Upstream product

• 3646-57-9 bis(4-nitrophenyl)diazene 
• 614-25-5 4,4'-dinitroazoxybenzene 
• 67-64-1 acetone 
• 1227476-15-4 Azobenzene 
• 100-01-6 4-nitro-aniline 
• 21190-30-7 N,N'-bis(4-cyanophenyl)hydrazine 
• 17082-12-1 trans-azobenzene 

Downstream Products

• 31464-31-0 N-methyl-4-nitro-4'-aminoazobenzene 
• 3646-57-9 bis(4-nitrophenyl)diazene 
• 21190-30-7 N,N'-bis(4-cyanophenyl)hydrazine 
• 538-41-0 4,4'-Diaminoazobenzene 
• 861596-22-7 N,N'-bis-[4-(4-amino-phenylazo)-phenyl]-hydrazine 
• 21371-47-1 bis-[4-(4-amino-phenylazo)-phenyl]-diazene 
• 106-50-3 1,4-phenylenediamine 
• 100-01-6 4-nitro-aniline 
• 730-40-5 disperse orange 3 
• 2198-74-5 4,4′-azobisbenzenamin 
• 102017-80-1 4-butyl-1,2-bis-(4-nitro-phenyl)-pyrazolidine-3,5-dione 
• 101722-57-0 1,2-bis-(4-nitro-phenyl)-4-propyl-pyrazolidine-3,5-dione 

Relevant articles and documents

When Do Strongly Coupled Diradicals Show Strongly Coupled Reactivity? Thermodynamics and Kinetics of Hydrogen Atom Transfer Reactions of Palladium and Platinum Bis(iminosemiquinone) Complexes

The 2,2′-biphenylene-bridged bis(iminosemiquinone) complexes (tBuClip)M [tBuClipH4 = 4,4′-di-tert-butyl-N,N′-bis(3,5-di-tert-butyl-2-hydroxyphenyl)-2,2′-diaminobiphenyl; M = Pd, Pt] can be reduced to the bis(aminophenoxide) complexes (tBuClipH2)M by reaction with hydrazobenzene (M = Pd) or by catalytic hydrogenation (M = Pt). The palladium complex with one aminophenoxide ligand and one iminosemiquinone ligand, (tBuClipH)Pd, is generated by comproportionation of (tBuClip)Pd with (tBuClipH2)Pd in a process that is both slow (0.06 M-1 s-1 in toluene at 23 °C) and only modestly favorable (Kcom = 1.9 in CDCl3), indicating that both N-H bonds have essentially the same bond strength. The mono(iminoquinone) complex (tBuClipH)Pt has not been observed, indicating that the platinum analogue shows no tendency to comproportionate (Kcom tBuClipH2)Pt to (tBuClip)Pd occurring with ?G° = ?8.9 kcal mol-1. The palladium complex (tBuClipH2)Pd reacts with nitroxyl radicals in two observable steps, with the first hydrogen transfer taking place slightly faster than the second. In the platinum analogue, the first hydrogen transfer is much slower than the second, presumably because the N-H bond in the monoradical complex (tBuClipH)Pt is unusually weak. Using driving force-rate correlations, it is estimated that this bond has a BDFE of 55.1 kcal mol-1, which is 7.1 kcal mol-1 weaker than that of the first N-H bond in (tBuClipH2)Pt. The two radical centers in the platinum, but not the palladium, complex thus act in concert with each other and display a strong thermodynamic bias toward two-electron reactivity. The greater thermodynamic and kinetic coupling in the platinum complex is attributed to the stronger metal-ligand ? interactions in this compound.