4,4'-Dinitrodiphenic acid cas 20246-81-5 powder

Product Overview:
4,4'-dinitro-1,1'-biphenyl-2,2'-dicarboxylic acid is an important organic synthesis intermediate and belongs to the biphenyl derivatives. Its molecular structure has three key chemical characteristics: nitro, carboxylic acid and biphenyl backbone, which makes it of special application value in the field of advanced materials science and medicinal chemistry.
Basic information

Chinese Name: 4,4'-dinitro-1,1'-biphenyl-2,2'-dicarboxylic acid

English name: 4,4'-Dinitro-[1,1'-biphenyl]-2,2'-dicarboxylic acid

CAS Number: 20246-81-5

Molecular formula: C₁₄H₈N₂O₈

Molecular weight: 332.22 g/mol

Physicochemical properties

Appearance: Typically light yellow to yellow crystalline powder.

Solubility: Soluble in polar organic solvents (e.g., dimethylformamide DMF, dimethyl sulfoxide DMSO), slightly soluble in alcohols, poorly soluble in water.

Chemical Properties:

Acidic: Contains two carboxyl groups, which are somewhat acidic and can react with bases to form salts.

Reducibility of nitro groups: Two nitro groups can be reduced to amino groups to form the corresponding diaminobiphenyl dicarboxylic acid, which is an extremely important chemical transformation.

Reactivity of carboxyl groups: Carboxyl groups can undergo reactions such as esterification and amidination to further modify molecular structures.

Steric hindrance effect: Two carboxyl groups and two nitro groups are in the adjacent position, causing a certain steric resistance, which may affect the selectivity of the reaction.

Synthesis method
It is usually synthesized using 2-nitrobenzoic acid or 2-nitrotoluene as the starting material through the following key steps:

Ullmann coupling reaction: Under copper catalysis, two molecular halogenated (such as iodine or brominated) o-nitrobenzoic acids (or their derivatives) are coupled to form biphenyl bonds.

Oxidation reaction (if toluene is used as raw material): If the starting raw material is 2-nitrotoluene, methyl needs to be oxidized to carboxyl groups after coupling.
The key to synthesis is the highly selective coupling of 2,2' bits.

Main applications:
The core value of this compound lies in its role as a high-performance polymer monomer precursor.

Key monomers of polybenzimidazole and polybenzooxazole polymers:

Core conversion: Reduce two nitro groups to amino groups to obtain 3,3'-diaminobiphenyl-4,4'-dicarboxylic acid or its derivatives.

Polymer Synthesis: The above diamino compounds are polycondensed with monomers such as diacids, dialdehydes, or diacid anhydrides, which can synthesize a class of polymers called polybenzimidazole or polybenzooxazole.

Final Material Application:

High-performance fibers and films: These polymers offer extremely high thermal stability, excellent mechanical strength, excellent chemical stability, and flame retardancy. It can be used to manufacture spacecraft heat-resistant parts, firefighting suits, protective gloves, etc. Proton exchange membrane: Polybenzimidazole doped with phosphoric acid is one of the core materials of high-temperature proton exchange membrane fuel cells, Summary 4,4'-dinitro-1,1'-biphenyl-2,2'-dicarboxylic acid (CAS 20246-81-5)

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