1-[4-(2,4-Dinitrophenoxy)phenoxy]-2,4-dinitrobenzene
[CAS# 4434-08-6]

Identification

• Classification: Chemical reagent >> Organic reagent >> Nitro compound
• Name: 1-[4-(2,4-Dinitrophenoxy)phenoxy]-2,4-dinitrobenzene
• Synonyms: 1,1'-[1,4-Phenylenebis(oxy)]bis(2,4-dinitrobenzene)
• Molecular Formula: C₁₈H₁₀N₄O₁₀
• Molecular Weight: 442.29
• CAS Registry Number: 4434-08-6
• SMILES: C1=CC(=CC=C1OC2=C(C=C(C=C2)[N+](=O)[O-])[N+](=O)[O-])OC3=C(C=C(C=C3)[N+](=O)[O-])[N+](=O)[O-]

Properties

• Density: 1.6±0.1 g/cm³ Calc.^*
• Boiling point: 546.9±50.0 ºC 760 mmHg (Calc.)^*
• Flash point: 218.9±32.1 ºC (Calc.)^*
• Index of refraction: 1.682 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Discovory and Applicatios

1‑[4-(2,4-Dinitrophenoxy)phenoxy]-2,4-dinitrobenzene is a nitroaromatic ether compound in which two aromatic rings bearing nitro groups are connected through an ether linkage. Each aromatic ring contains nitro substituents at the 2 and 4 positions, making the rings highly electron-deficient. This electron deficiency influences both the chemical reactivity and physical properties of the molecule. Compounds of this type are generally solid at room temperature, have relatively high melting points, and are insoluble in water while being soluble in organic solvents. The electron-withdrawing nitro groups also activate the aromatic rings toward nucleophilic aromatic substitution reactions, facilitating the formation of additional ether or other functional linkages.

The structural motif of 1-[4-(2,4-dinitrophenoxy)phenoxy]-2,4-dinitrobenzene is characteristic of nitroaromatic ethers, which are widely employed in synthetic organic chemistry as intermediates and model compounds. Nitroaromatic ethers are often used to investigate the reactivity of electron-deficient aromatic systems and to prepare more complex nitroaromatic structures. The presence of multiple nitro groups allows further chemical transformation, such as reduction to amino groups, which can then serve as precursors for dyes, polyamines, or other functionalized molecules.

The synthesis of compounds in this class typically involves nucleophilic aromatic substitution (SNAr) reactions. In such reactions, a phenoxide ion generated from a substituted phenol attacks an electron-deficient aromatic halide, displacing a leaving group and forming the ether linkage. The nitro substituents on the aromatic ring enhance the susceptibility of the halide to nucleophilic attack, enabling efficient formation of the multi-nitro ether structure. Variations of this method, including the use of different linkers or substituted phenols, allow the assembly of a wide variety of electron-poor aromatic ethers with controlled substitution patterns.

Physically, 1-[4-(2,4-dinitrophenoxy)phenoxy]-2,4-dinitrobenzene exhibits low volatility and limited solubility in polar solvents due to its extensive conjugated and electron-withdrawing framework. Its thermal stability and crystalline nature make it suitable for research applications that require stable, solid nitroaromatic compounds. Nitroaromatic ethers are generally handled with caution in laboratory settings, as many compounds in this class are toxic and may pose health hazards upon exposure.

In terms of applications, the compound is primarily used as a research chemical or synthetic intermediate. It serves as a model system for studying the reactivity of electron-deficient aromatic compounds and for preparing derivatives with additional functional groups. Its bifunctional nitro-substituted structure allows chemists to explore sequential substitution reactions or reductions, enabling the creation of amino-functionalized derivatives that are valuable in organic synthesis and materials chemistry.

Overall, 1-[4-(2,4-dinitrophenoxy)phenoxy]-2,4-dinitrobenzene exemplifies the class of electron-deficient nitroaromatic ethers. Its molecular architecture, featuring multiple nitro groups and ether linkages, provides a platform for studying nucleophilic aromatic substitution, designing synthetic intermediates, and exploring chemical transformations that exploit the reactivity of highly electron-poor aromatic systems. Its applications remain centered on research and synthetic chemistry rather than large-scale industrial use, where it functions primarily as a versatile and stable intermediate for further functionalization.

References

2021. Chemical validation of a druggable site on Hsp27/HSPB1 using in silico solvent mapping and biophysical methods. Bioorganic & Medicinal Chemistry, 31.
DOI: 10.1016/j.bmc.2020.115990