621-96-5

Usage

Uses

Used in Textile Industry:
4,4'-Stilbenediamine is used as a precursor in the production of dyes and optical brightening agents for textiles. Its application enhances the color and brightness of fabrics, improving their aesthetic appeal and performance.
Used in Pharmaceutical Industry:
This chemical compound is utilized in the synthesis of pharmaceuticals, contributing to the development of new drugs and therapeutic agents. Its unique chemical properties make it a valuable component in the creation of various medicinal formulations.
Used in Polymer Industry:
4,4'-Stilbenediamine serves as a photo-initiator in polymerization reactions, playing a crucial role in the formation of polymers used in various applications, such as plastics, coatings, and adhesives. Its ability to initiate polymerization under specific conditions makes it an essential component in the polymer industry.

Upstream product

• 619-93-2 4,4'-dinitro stilbene 
• 65198-02-9 3-(4-aminophenyl)-acrylic acid methyl ester 
• 461461-89-2 4-aminocinnamyl alcohol 
• 621-82-9 Cinnamic acid 
• 2393-18-2 p-aminocinnamic acid 
• 619-89-6 p-nitrocinnamic acid 
• 33267-39-9 N,N'-diacetyl-4,4'-diaminostilbene 
• 2922-41-0 (p-aminophenyl)alanine 
• 2609-49-6 diethyl p-nitrobenzylphosphonate 
• 1112-55-6 tetravinylsilane 
• 540-37-4 p-aminoiodobenzene 
• 100-14-1 4-nitrobenzyl chloride 
• 99-99-0 1-methyl-4-nitrobenzene 
• 7803-57-8 hydrazine hydrate 

Downstream Products

• 28149-69-1 N,N'-bis-(4-dimethylamino-benzylidene)-stilbene-4,4'-diyldiamine 
• 588-59-0 stilbene 
• 659-22-3 4,4'-dihydroxystilbene 
• 1034911-58-4 [(E)-N,N'-bis(4-chloro-6-methoxy-1,3,5-triazin-2-yl)-4,4'-diaminostilbene]-[α-cyclodextrin]-[2]-[rotaxane] 
• 621-95-4 4,4'-diaminodihydrostilbene 
• 17635-36-8 N,N'-bis(salicylidine)-4,4'-diaminostilbene 

Relevant academic research and scientific papers

Second-generation aryl isonitrile compounds targeting multidrug-resistant Staphylococcus aureus

Antibiotic resistance remains a major global public health threat that requires sustained discovery of novel antibacterial agents with unexploited scaffolds. Structure-activity relationship of the first-generation aryl isonitrile compounds we synthesized led to an initial lead molecule that informed the synthesis of a second-generation of aryl isonitriles. From this new series of 20 compounds, three analogues inhibited growth of methicillin-resistant Staphylococcus aureus (MRSA) (from 1 to 4 μM) and were safe to human keratinocytes. Compound 19, with an additional isonitrile group exhibited improved activity against MRSA compared to the first-generation lead compound. This compound emerged as a candidate worthy of further investigation and further reinforced the importance of the isonitrile functionality in the compounds’ anti-MRSA activity. In a murine skin wound model, 19 significantly reduced the burden of MRSA, similar to the antibiotic fusidic acid. In summary, 19 was identified as a new lead aryl isonitrile compound effective against MRSA.

The 4.4′-benzidine rearrangement of 4-alkyl substituted hydrazobenzenes

When treated with dilute inorganic acids N,N′-diarylhydrazines (hydrazobenzenes) with an alkyl substituent in the 4-position undergo [5,5]-sigmatropic rearrangement reactions to furnish 4-(4′-aminophenyl)-4-alkylcyclohexa-2,5-dienimines (ipso-benzidines) in moderate to excellent yields. Steric bulk of the 4-alkyl substituent in the starting material decreases the yield of the respective ipso-benzidine. Additional electron-donating alkyl substituents in the ortho- and/or meta-positions on both rings generally promote the reaction and consequently increase the yield of the 4.4′-benzidine rearrangement product. Described herein are our findings regarding the scope and limits of this unusual benzidine rearrangement.

Ultrahigh performance bio-based polyimides from 4,4′-diaminostilbene

We have developed a novel route for the synthesis of high-performance bio-polyimides (PIs) microbially-derived from photo-responsive aromatic diamine 4,4′-diaminostilbene (DAS) and its reduced counterpart 4, 4′-(ethane-1,2-diyl)dianiline (EDDA). DAS and EDDA were condensed with various commercially-available dianhydrides to obtain a series of poly(amic acid)s (PAAs) and PIs which were characterized in terms of their thermal, mechanical, and photo-functions. These bio-based PAAs showed a very high viscosity of 6.62 dL/g, and the PIs showed ultrahigh thermal resistance with Td10 values over 600 °C, which were higher than that of any bio-based plastic reported thus far. They also showed Tg values above 250 °C, and tensile strength of over 132 MPa, which is higher than that of Kapton. The PIs also showed photo-functional behavior based on stilbene-based photoreactions.

Fluorescence phenomena in nerve-labeling styryl-type dyes

Several classes of diversely substituted styryl type dyes have been synthesized with the goal of extending their expected fluorescent properties as much toward red as possible given the constraint that they maintain drug-like properties and retain high affinity binding to their biological target. We report on the synthesis, optical properties of a series of styryl dyes (d1-d14), and the anomalous photophysical behavior of several of these donor-acceptor pairs separated by long conjugated π-systems (d7-d10). We further describe an unusual dual emission behavior with two distinct ground state conformers which could be individually excited to locally excited (LE) and twisted intramolecular charge transfer (TICT) excited state in push-pull dye systems (d7, d9 and d10). Additionally, unexpected emission behavior in dye systems d7 and d8 wherein the amino-derivative d7 displayed a dual emission in polar medium while the N,N-dimethyl derivative d8 and other methylated derivatives d12-d14 showed only LE emission but did not show any TICT emission. Based on photophysical and nerve binding studies, we down selected compounds that exhibited the most robust fluorescent staining of nerve tissue sections. These dyes (d7, d9, and d10) were subsequently selected for in vivo fluorescence imaging studies in rodents using the small animal multispectral imaging instrument and the dual-mode laparoscopic instrument developed in-house.

Facile, mild and convenient preparation and characterization of some novel schiff base ligands from synthetic diamines and salicylaldehyde

Some novel Schiff base ligands have been prepared through condensation of salicylaldehyde with synthetic various primary diamines under mild reaction conditions. The used aromatic diamines were synthesized in good yields starting from low-cost commercially available materials. In these reactions, the Schiff base products have been afforded with excellent yields and appropriate reaction times. The structure of these ligands has been characterized by IR, 1H NMR and 13C NMR techniques.

Supported palladium nanoparticles as heterogeneous ligand-free catalysts for the Hiyama C-C coupling of vinylsilanes and halobenzenes leading to styrenes

The Hiyama C-C coupling reaction of a wide range of aryl iodides and vinylsilanes has been performed using ligand-free solid catalysts based on supported palladium nanoparticles. Among the supports tested (Mg, TiO 2, CeO2 and active carbon), the most active catalysts were those in which palladium is supported on MgO and TiO2. Analogous Pt and Au materials were inefficient to promote this reaction. Leaching tests suggest that there is some contribution of dissolved Pd since Pd in solution has been detected and the scavenging test decreases the initial reaction rate. Although the solid Pd catalysts can be reused, it was, however, observed that they undergo a certain deactivation upon use that can be attributed to several factors including the presence of inorganic compounds on the catalyst, Pd leaching or agglomeration of Pd NPs.