619-93-2

Basic information

• Product Name: cis-4,4'-dinitrostilbene
• Synonyms: cis-4,4'-dinitrostilbene;(Z)-4,4'-Dinitrostilbene;(αZ)-4,4'-Dinitrostilbene;1-nitro-4-[(Z)-2-(4-nitrophenyl)ethenyl]benzene
• CAS NO: 619-93-2
• Molecular Formula: C₁₄H₁₀N₂O₄
• Molecular Weight: 270.2402
• EINECS: 210-620-5
• Mol File: 619-93-2.mol
• Article Data: 32

Chemical Properties

• Boiling Point: 413.36°C (rough estimate)
• Appearance: /
• Density: 1.2809 (rough estimate)
• Refractive Index: 1.6500 (estimate)
• CAS DataBase Reference: cis-4,4'-dinitrostilbene(CAS DataBase Reference)
• NIST Chemistry Reference: cis-4,4'-dinitrostilbene(619-93-2)
• EPA Substance Registry System: cis-4,4'-dinitrostilbene(619-93-2)

Safety Data

• Hazardous Substances Data: 619-93-2(Hazardous Substances Data)

Usage

General Description

Cis-4,4'-dinitrostilbene is a chemical compound that belongs to the stilbene family, which is known for its fluorescent properties. cis-4,4'-dinitrostilbene is composed of two nitro groups attached to a central stilbene backbone, with the nitro groups located at the 4th position on each benzene ring. Cis-4,4'-dinitrostilbene is commonly used as a precursor in the synthesis of various organic compounds and pharmaceuticals. It is also used in the production of dyes, pigments, and fluorescent materials, as well as in the research of photochemical and photophysical processes. Additionally, this compound has potential applications in the field of organic electronics and optoelectronics. Its unique structure and properties make cis-4,4'-dinitrostilbene a valuable and versatile chemical in various scientific and industrial processes.

Upstream product

• 736-31-2 trans-4,4'-dinitrostilbene 
• 98-95-3 nitrobenzene 
• 100-14-1 4-nitrobenzyl chloride 
• 91-22-5 quinoline 
• 6277-62-9 2,3t-bis-(4-nitro-phenyl)-acrylic acid 
• 1530-42-3 (4-nitrobenzyl)triphenylphosphonium chloride 
• 555-16-8 4-nitrobenzaldehdye 
• 67-56-1 methanol 
• 4485-08-9 4-nitrosonitrobenzene 
• 60-29-7 diethyl ether 
• 99-99-0 1-methyl-4-nitrobenzene 
• 917-58-8 potassium ethoxide 
• 95-92-1 oxalic acid diethyl ester 
• 619-73-8 4-nitrobenzyl chloride 

Downstream Products

• 736-31-2 trans-4,4'-dinitrostilbene 
• 7314-06-9 (E)-4,4'-diaminostilbene 
• 968-01-4 trans-4,4'-dinitrostilbeneoxide 
• 128899-05-8 trans-4,4'-nitrostilbenexide 
• 14688-37-0 cis-p,p'-dinitrostilbene oxide 
• 659-22-3 trans-4,4'-dihydroxystilbene 
• 47241-75-8 (E)-4,4’-diacetoxystilbene 
• 6067-45-4 4,4'-dinitrobenzil 
• 621-95-4 4,4'-diaminodihydrostilbene 
• 62-23-7 4-nitro-benzoic acid 
• 27297-07-0 meso-p,p'-dinitrostilbene dibromide 
• 13295-04-0 1.2-bis(4-nitrophenyl)ethane-1,2-diol 
• 621-96-5 4,4'-diaminostilbene 
• 93968-39-9 meso-1,2-dibromo-1,2-di(4-nitrophenyl)-2-ethane 

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.

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.

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.