2501-02-2

Usage

Uses

Used in Dye Industry:
4,4'-Dinitrostilbene is used as a dye intermediate for the production of various dyes. Its chemical structure allows it to be a key component in the synthesis of dyes that impart vibrant colors to different materials.
Used in Optical Brightening Agents Production:
In the textile and paper industry, 4,4'-dinitrostilbene is used as a starting material for the synthesis of optical brightening agents. These agents enhance the appearance of textiles and paper products by reflecting light and giving them a brighter, more appealing look.
Used in Pharmaceutical Industry:
4,4'-Dinitrostilbene has been studied for its potential use as a pharmaceutical intermediate. Its unique chemical properties make it a candidate for the development of new drugs and pharmaceutical compounds.
Used in Advanced Materials Development:
4,4'-DINITROSTILBENE is also being explored for its potential in the development of new materials with advanced optical properties. Its ability to interact with light makes it a promising candidate for applications in optoelectronics and photonics.
However, it is crucial to handle 4,4'-dinitrostilbene with care due to its toxic nature and potential to cause irritation to the skin, eyes, and respiratory system. Proper safety measures should be taken during its production, use, and disposal to minimize health risks and environmental impact.

Upstream product

• 110-86-1 pyridine 
• 93968-39-9 meso-1,2-dibromo-1,2-di(4-nitrophenyl)-2-ethane 
• 99-99-0 1-methyl-4-nitrobenzene 
• 124-41-4 sodium methylate 
• 141-52-6 sodium ethanolate 
• 16993-83-2 sodium 2-ethoxyethoxide 
• 104-03-0 4-nitrobenzeneacetic acid 
• 555-16-8 4-nitrobenzaldehdye 
• 67-56-1 methanol 
• 100-14-1 4-nitrobenzyl chloride 
• 4485-08-9 4-nitrosonitrobenzene 
• 60-29-7 diethyl ether 
• 917-58-8 potassium ethoxide 
• 95-92-1 oxalic acid diethyl ester 

Downstream Products

• 105222-70-6 α,α'-dichloro-4,4'-dinitro-bibenzyl 
• 93968-39-9 meso-1,2-dibromo-1,2-di(4-nitrophenyl)-2-ethane 
• 621-96-5 4,4'-diaminostilbene 
• 13295-04-0 1.2-bis(4-nitrophenyl)ethane-1,2-diol 
• 27297-07-0 meso-p,p'-dinitrostilbene dibromide 
• 62-23-7 4-nitro-benzoic acid 
• 621-95-4 4,4'-diaminodihydrostilbene 
• 659-22-3 4,4'-dihydroxystilbene 

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.

Olefin cross-metathesis/Suzuki-Miyaura reactions on vinylphenylboronic acid pinacol esters

A series of alkenyl phenylboronic acid pinacol esters has been synthesized via an olefin cross-metathesis reaction of vinylphenylboronic acid pinacol ester derivatives. After catalytic hydrogenation, the resulting boronates were coupled via a microwave-mediated Suzuki-Miyaura reaction to afford a library of biarylethyl aryl and biarylethyl cycloalkyl derivatives. A complementary reaction sequence involved an initial Suzuki-Miyaura coupling.

Dehydrogenation of nitro derivatives of bibenzyl to corresponding nitro stilbene with dioxygen catalyzed by 2,2,6,6-tetramethylpiperidine-1-oxyl

A simple and effective oxidative dehydrogenation of nitro derivatives of bibenzyl was developed using a mixture of 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) and metal salts as catalyst under an atmospheric pressure of oxygen. The oxidation of several nitro derivatives of bibenzyl led to corresponding nitro stilbene in good yields, and the yields increased with the increase in the substituted nitro group on the bibenzyl. For example, the aerobic dehydrogenation of 2,2,4,4,6,6-hexanitrobibenzyl in the presence of a catalytic amount of TEMPO with metal salts gave 2,2,4,4,6,6-hexanitrostilbene in 81 % yield and 4,4-dinitrostilbene-2,2-disulfonic acid (75 %) was obtained from 4,4-dinitrobibenzyl-2,2-disulfonic acid. Iranian Chemical Society 2012.

Synthesis of stilbene analogues by one-pot oxidation-Wittig and oxidation-Wittig-Heck reaction

Synthesis of symmetrical (and unsymmetrical) stilbene derivatives is achieved by a combination of one-pot steps of Kornblum type oxidation of benzyl halide, its simultaneous in situ formation of phosphonium salt, and subsequently their Wittig reaction. In other variant it is oxidized to aldehyde, treated with ylide generated from phosphonium salt (CH3PPh3X) to give styrene, and subjected to Pd catalyzed Heck reaction with arylhalide to give stilbenes as the three-step one-pot sequence.

On the dual role of N-heterocyclic carbenes as bases and nucleophiles in reactions with organic halides

The synthetic consequences of different basicities, nucleophilicities, and sterics of N-heterocyclic carbenes have been studied in reactions of imidazolin-2-ylidenes with organic halides. Highly nucleophilic and less basic carbenes cleanly gave alkyli-deneimidazolines, the deoxy analogues of Breslow-type intermediates. More basic NHCs engaged in unwanted deprotonation or dehydrohalogenation reactions. Georg Thieme Verlag Stuttgart. New York.

Solvolytic stereoselective debromination of vic-dibromides with HMPA

A simple and efficient procedure for the debromination of vic-dibromides has been reported with hexamethylphosphoric triamide at 155-160°C under a nitrogen atmosphere without the aid of any reagent.

REACTIVITY OF THE ACIDS OF TRIVALENT PHOSPHORUS AND THEUR DERIVATIVES. PART II. THE REACTION OF TRIVALENT PHOSPHORUS ACID SALTS WITH THE BENZYLIC HALIDES SYSTEM

The reaction of the benzylic halides systems with sodium dialkylphosphites as well as the sodium salt of dibenzylphosphine oxide in THF and alcohols as the solvents is described.According to the constitution of the starting materials, the formation of the P-C bond, dehalogenation or dimerization occurs.Probable mechanisms namely SET and X-philic substitution are discussed.Key words: Benzylic halides system, dialkylphosphites, dibenzylphosphine oxide, Michaelis-Becker reaction, X-philic substitution.

Electrochemical reduction of certain fluorenyl and xanthenyl olefins

The reduction of certain fluorene and xanthene containing olefins at a mercury electrode using cyclic voltammetry has been investigated.In DMF, fluorene-9-(4-nitrophenyl)methylene (1) reveals two distinct reversible one-electron redox waves corresponding to anion radical and dianion formation.Some other olefins particularly stilbenes (9-14) and substituted propenones (7,8) show commonality in the emergence of at least one distinct reversible reduction couple.Anion radicals of nearly all of the olefins (1-14) studied in this work generated electrochemically or by chemical 1-electron reductants, exhibited considerable stability.

C-ALKYLATION OF β-DIKETONES WITH BENZYLPYRIDINIUM SALTS. EVIDENCE FOR CHAIN RADICAL MECHANISMS

1-(p-Substituted benzyl)-2,4,6-triphenylpyridinium cations react with β-diketone anions by mechanisms which depend on the para-substituent.The p-methoxybenzyl derivative undergoes SN1 displacement yielding O- and C-benzylated products.The p-nitrobenzyl compound reacts by a chain radicaloid mechanism and gives high yields of C-p-nitrobenzylated diketones.The parent benzyl compound forms some C- and some O-benzylated products, together with bibenzyl, probably by a radical chain reaction which was suppressed by radical traps.