2501-02-2

Basic information

• Product Name: 4,4'-DINITROSTILBENE
• Synonyms: TRANS-1,2-BIS(4-NITROPHENYL)ETHENE;TRANS-4,4'-DINITROSTILBENE;4,4'-DINITROSTILBENE;1-NITRO-4-(4-NITROSTYRYL)BENZENE;4,4''-DINITROSTILBENE 98+%;1,1'-(1,2-Ethenediyl)bis(4-nitrobenzene);4,4'-Dinitro-trans-stilbene;p,p'-Dinitrostilbene
• CAS NO: 2501-02-2
• Molecular Formula: C₁₄H₁₀N₂O₄
• Molecular Weight: 270.24
• Product Categories: Stilbenes (substituted);Stilbenes
• Mol File: 2501-02-2.mol
• Article Data: 23

Chemical Properties

• Melting Point: 295 °C
• Boiling Point: 394.6°Cat760mmHg
• Flash Point: 182.7°C
• Appearance: /
• Density: 1.376g/cm³
• CAS DataBase Reference: 4,4'-DINITROSTILBENE(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4'-DINITROSTILBENE(2501-02-2)
• EPA Substance Registry System: 4,4'-DINITROSTILBENE(2501-02-2)

Safety Data

• Hazardous Substances Data: 2501-02-2(Hazardous Substances Data)

Usage

General Description

4,4'-Dinitrostilbene is a synthetic organic compound with the chemical formula C14H10N2O4. It is a crystalline yellow solid that is insoluble in water but soluble in organic solvents. 4,4'-Dinitrostilbene is primarily used as a dye intermediate and as a starting material for the synthesis of other organic compounds. It is also used in the production of optical brightening agents, which are used to enhance the appearance of textiles and paper products. Additionally, 4,4'-dinitrostilbene has been studied for its potential use as a pharmaceutical intermediate and in the development of new materials with advanced optical properties. However, it is important to handle this compound with care, as it is toxic and may cause irritation to the skin, eyes, and respiratory system.

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 
• 659-22-3 4,4'-dihydroxystilbene 
• 62-23-7 4-nitro-benzoic acid 
• 621-95-4 4,4'-diaminodihydrostilbene 

Relevant articles and documents

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.

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.

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.