Production Method 1

1646-54-4

87199-17-5

850559-54-5

Reaction Conditions

1.1 Reagents: Potassium carbonate Catalysts: Tetrakis(triphenylphosphine)palladium Solvents: 1,2-Dimethoxyethane ,  Water ;  6 h, reflux

Reference

Synthesis of rigid polyaromatic dialdehydes

Kozakova, Michala; et al, Synthetic Communications, 2005, 35(2), 161-167

[1,1′:4′,1′′-Terphenyl]-4,4′′-dicarboxaldehyde, 2′,3′,5′,6′-tetramethyl- (9CI) Raw materials

• 3,6-Dibromodurene
• (4-formylphenyl)boronic acid

[1,1′:4′,1′′-Terphenyl]-4,4′′-dicarboxaldehyde, 2′,3′,5′,6′-tetramethyl- (9CI) Preparation Products

• [1,1′:4′,1′′-Terphenyl]-4,4′′-dicarboxaldehyde, 2′,3′,5′,6′-tetramethyl- (9CI) (850559-54-5)

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• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives P-terphenyls
• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Terphenyls P-terphenyls

Introduction to [1,1′:4′,1′′-Terphenyl]-4,4′′-dicarboxaldehyde, 2′,3′,5′,6′-tetramethyl- (9CI) and Its Applications in Modern Chemical Biology

The compound with the CAS number 850559-54-5, specifically named as [1,1′:4′,1′′-Terphenyl]-4,4′′-dicarboxaldehyde, 2′,3′,5′,6′-tetramethyl- (9CI), represents a fascinating molecule in the realm of chemical biology. This terphenyl derivative has garnered significant attention due to its unique structural features and potential applications in various biochemical pathways. The presence of multiple aromatic rings interconnected by methylene bridges provides a stable scaffold that can be modified for specific biological interactions.

In recent years, the study of multifunctional organic compounds has seen remarkable advancements, particularly in the development of molecular tools for drug discovery and biomolecular research. The [1,1′:4′,1′′-Terphenyl]-4,4′′-dicarboxaldehyde, 2′,3′,5′,6′-tetramethyl- (9CI) structure offers a rich platform for designing ligands that can interact with biological targets such as enzymes and receptors. The aldehyde functional groups at the para positions of the outer phenyl rings enhance its reactivity, making it a valuable intermediate in synthesizing more complex molecules.

One of the most intriguing aspects of this compound is its potential application in the development of novel fluorescent probes. Fluorescent dyes are widely used in cellular imaging and diagnostics due to their ability to emit light upon excitation with specific wavelengths. The rigid terphenyl core of [1,1′:4′,1′''-Terphenyl]-4,4''-dicarboxaldehyde, 2''',3''',5''',6'''-tetramethyl- (9CI) can be engineered to incorporate fluorophores that are sensitive to environmental changes such as pH or redox potential. This property makes it an excellent candidate for real-time monitoring of biological processes within living cells.

Moreover, the compound's tetramethyl substitution pattern at the inner phenyl ring enhances its solubility in organic solvents while maintaining its stability under various conditions. This balance is crucial for its application in high-throughput screening assays where compatibility with diverse solvent systems is essential. Researchers have leveraged these properties to develop novel screening platforms for identifying small molecules that modulate specific biological pathways.

The aldehyde groups in [1,1':4',1''-Terphenyl]-4',4''-dicarboxaldehyde also serve as versatile handles for further chemical modifications. These groups can undergo condensation reactions with amines or hydrazines to form Schiff bases or hydrazones respectively. Such derivatives have been explored for their potential antimicrobial and anti-inflammatory properties. Recent studies have shown that certain Schiff base derivatives derived from this terphenyl compound exhibit promising activity against drug-resistant bacterial strains.

In the context of drug discovery pipelines, the structural motif of [1',1':4',1'''-Terphenyl]-4',4'''-dicarboxaldehyde, 2'',3'',5'',6'''-tetramethyl-(9CI), has inspired the design of inhibitors targeting various therapeutic targets including kinases and proteases. The aromatic stacking interactions provided by the terphenyl core can be exploited to enhance binding affinity towards protein targets. Additionally, the presence of multiple reactive sites allows for the synthesis of bispecific inhibitors that can simultaneously bind two different targets—a strategy increasingly employed in modern drug development.

The compound's stability under various storage conditions makes it a practical choice for industrial applications where long-term shelf life is critical. This stability is attributed to its robust aromatic framework and minimal susceptibility to degradation under ambient conditions. Furthermore

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