5,5'-Carbonylbis(2-benzofuran-1,3-dione) - 1-(4-aminophenyl)-1,3,3-trimethyl-5-indanamine
[CAS# 62929-02-6]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Amine
• Name: 5,5'-Carbonylbis(2-benzofuran-1,3-dione) - 1-(4-aminophenyl)-1,3,3-trimethyl-5-indanamine
• Molecular Formula: C₃₅H₂₈N₂O₇
• Molecular Weight: 588.61
• CAS Registry Number: 62929-02-6
• EC Number: 676-824-5
• SMILES: CC1(C)CC(C)(c2ccc(N)cc2)c2ccc(N)cc21.O=C(c1ccc2c(c1)C(=O)OC2=O)c1ccc2c(c1)C(=O)OC2=O

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Discovory and Applicatios

5,5′-Carbonylbis(2-benzofuran-1,3-dione) - 1-(4-aminophenyl)-1,3,3-trimethyl-5-indanamine is a structurally complex organic compound consisting of two principal substructures linked by a carbonyl bridge. One substructure is a benzofuran-1,3-dione core, and the other is an indanamine derivative bearing a 4-aminophenyl substituent and two methyl groups. Compounds that combine multiple aromatic heterocycles and amine functionalities are often encountered in medicinal chemistry, materials research, and molecular probes because the juxtaposition of rigid aromatic systems with basic amine groups can give rise to interesting electronic, binding, and structural properties.

The benzofuran-1,3-dione portion of the molecule consists of a benzene ring fused to a furan ring with two carbonyl groups at the 1 and 3 positions. This di-carbonyl ring system is a derivative of isobenzofuran-1,3-dione, a reactive scaffold that participates in nucleophilic addition and cycloaddition reactions. The presence of two such units connected by a carbonyl group (forming 5,5′-carbonylbis units) suggests that the overall compound can exhibit rigidity and planarity in regions of the molecule, influencing how it might interact with biological targets or assemble in the solid state.

The indanamine fragment contains a bicyclic indane ring system with an amine substituent at the 5-position that is linked to a 4-aminophenyl group. The indane core is a saturated bicyclic structure comprised of a benzene ring fused to a cyclopentane. The 1,3,3-trimethyl substitution pattern on the indane ring introduces steric bulk and lipophilicity, and the presence of a basic amine connected via the 4-aminophenyl group can confer water solubility and potential sites for protonation under acidic conditions. Basic amine groups are common pharmacophores in biologically active compounds because they can form ionic interactions with acidic residues in proteins, and the 4-aminophenyl substituent adds an additional aromatic domain that can participate in π–π stacking or hydrophobic interactions.

Synthesis of this compound would likely involve sequential construction of the benzofuran-dione and indanamine building blocks, followed by coupling through the carbonyl carbon. Benzofuran-1,3-dione derivatives are typically prepared by oxidation of corresponding benzofuran precursors or via cyclization of appropriate o-hydroxyaryl ketones. The indanamine derivative can be synthesized by functional group transformations on indanone precursors, including reductive amination to introduce the amine and methylation steps to install the trimethyl substituents. The final carbonyl linkage connecting the two benzofuran-dione units would be generated through condensation or acylation reactions that form the bis-acyl structure.

Compounds that combine multiple aromatic and heterocyclic domains with basic amine side chains have been explored in various areas of chemical research. In medicinal chemistry, such hybrid structures are often investigated as potential ligands for protein targets, including enzymes, receptors, and nucleic acid binding sites. The diversity of aromatic surfaces and basic functional groups allows for fine tuning of affinity and selectivity. In materials science, polyaromatic compounds with bridging carbonyl groups can exhibit interesting photophysical properties, such as fluorescence or charge transport characteristics, although the specific photochemistry of this compound would depend on detailed experimental evaluation.

The presence of multiple reactive functional groups in 5,5′-Carbonylbis(2-benzofuran-1,3-dione) - 1-(4-aminophenyl)-1,3,3-trimethyl-5-indanamine also implies that it could be used as a synthetic intermediate. The di-carbonyl benzofuran units offer sites for further nucleophilic attack or condensation, and the primary amine on the phenyl group can participate in amide bond formation, urea or carbamate formation, or reductive coupling. Such versatility is often exploited in multi-step organic synthesis to build libraries of analogues for structure–activity relationship studies or to introduce reporter tags in chemical biology applications.

From a physical standpoint, compounds with fused aromatic rings and multiple substituents tend to have high melting points and limited solubility in water, while being more soluble in organic solvents such as dichloromethane, tetrahydrofuran, or dimethyl sulfoxide. Protonation of the amine group under acidic conditions can increase aqueous solubility, which may be beneficial for formulation in biological assays.

Overall, 5,5′-Carbonylbis(2-benzofuran-1,3-dione) - 1-(4-aminophenyl)-1,3,3-trimethyl-5-indanamine represents a multifunctional organic framework combining aromatic heterocycles, a bridging carbonyl structure, and a basic amine side chain. Its structural features reflect design motifs common to advanced synthetic targets in organic chemistry and provide potential utility as a scaffold for further functionalization or as a probe in chemical research.