25144-42-7

Basic information

• Product Name: (E)-2,6-Dichlorostilbene
• Synonyms: (E)-1-(2,6-Dichlorophenyl)-2-phenylethene;(E)-2,6-Dichlorostilbene
• CAS NO: 25144-42-7
• Molecular Formula: C14H10Cl2
• Molecular Weight: 249.14
• Mol File: 25144-42-7.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (E)-2,6-Dichlorostilbene(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-2,6-Dichlorostilbene(25144-42-7)
• EPA Substance Registry System: (E)-2,6-Dichlorostilbene(25144-42-7)

Safety Data

• Hazardous Substances Data: 25144-42-7(Hazardous Substances Data)

Upstream product

• 1449-46-3 benzyltriphenylphosphonium bromide 
• 83-38-5 2,6-dichlorobenzaldehyde 
• 100-52-7 benzaldehyde 
• 28469-92-3 2,6-dichlorostyrene 
• 71-43-2 benzene 
• 37532-04-0 N'-(2,6-dichlorobenzylidene)-4-methylbenzene-1-sulfonohydrazide 
• 100-44-7 benzyl chloride 
• 100-39-0 benzyl bromide 
• 1080-32-6 O,O-diethyl benzylphosphonate 

Downstream Products

• 1575599-10-8 C₁₄H₈Cl₂O₂ 

Relevant articles and documents

Synthesis of 1,2-diarylethylenes by Pd-catalyzed one-pot reaction of benzyl halides, tosylhydrazide, and aryl aldehydes

Background: Substituted olefins are versatile functional groups and intermediates in chemistry, medicine, electronics, and optics and materials science fields because of their unique properties. One important class of substituted olefins 1,2-diarylethylenes have attracted considerable attention due to their presence in both natural products and pharmacologically active substances. Methods: In this paper, we developed a one-pot two-step coupling reaction of aryl aldehydes, tosylhydrazide with benzyl halides by using inexpensive Pd(PPh3)4 as catalyst, leading to a variety of 1,2- diphenylethenes derivatives with moderate to good yields. Results: The desired 1,2-diarylethylenes were obtained in 46-96% yields via Pd(0)-catalyzed one-pot reaction of benzyl halides, tosylhydrazide, and aryl aldehydes. Conclusion: The catalytic system presented here enables the use of easily accessible starting materials and good functional group tolerance.

THERAPEUTIC AGENTS FOR SKIN DISEASES AND CONDITIONS

The present invention relates to method(s) of treating a subject afflicted with a skin disease or condition, the method comprising administering to the subject or patient in need a composition comprising a therapeutically effective amount of a substituted cis or trans- stilbene or a stilbene hybrid. A method of treating or reducing the likelihood of a skin disease or condition in a patient is an additional embodiment of the present invention. Preferred pharmaceutical compositions of the invention include nanoemulsions comprising a therapeutically effective amount of a substituted cis or trans-stilbene or stilbene hybrid and at least one antibiotic.

Straightforward synthesis of phenanthrenes from styrenes and arenes

Semi-one-pot synthesis of phenanthrenes from styrenes and arenes was developed through cross-dehydrogenative coupling. A sequence of Heck-type coupling and photo-cyclization were involved and a variety of functionalities were tolerated. This method provides an effective and practical protocol towards the synthesis of substituted phenanthrenes. The Royal Society of Chemistry 2012.

Substituted CIS- and trans-stilbenes as therapeutic agents

The present invention relates to method(s) of treating a subject afflicted with cancer or a precancerous condition, an inflammatory disease or condition, and/or stroke or other ischemic disease or condition, the method comprising administering to the subject or patient in need a composition comprising a therapeutically effective amount of a substituted cis or trans-stilbene.

Substituted trans-stilbenes, including analogues of the natural product resveratrol, inhibit the human tumor necrosis factor alpha-induced activation of transcription factor nuclear factor kappaB

The transcription factor nuclear factor kappaB (NF-κB), which regulates expression of numerous antiinflammatory genes as well as genes that promote development of the prosurvival, antiapoptotic state is up-regulated in many cancer cells. The natural product resveratrol, a polyphenolic trans-stilbene, has numerous biological activities and is a known inhibitor of activation of NF-κB, which may account for some of its biological activities. Resveratrol exhibits activity against a wide variety of cancer cells and has demonstrated activity as a cancer chemopreventive against all stages, i.e., initiation, promotion, and progression. The biological activities of resveratrol are often ascribed to its antioxidant activity. Both antioxidant activity and biological activities of analogues of resveratrol depend upon the number and location of the hydroxy groups. In the present study, phenolic analogues of resveratrol and a series of substituted trans-stilbenes without hydroxy groups were compared with resveratrol for their abilities to inhibit the human tumor necrosis factor alpha-induced (TNF-α) activation of NF-κB, using the Panomics NF-κB stable reporter cell line 293/NF-κB-luc. A series of 75 compounds was screened to identify substituted trans-stilbenes that were more active than resveratrol. Dose-response studies of the most active compounds were carried out to obtain IC50 values. Numerous compounds were identified that were more active than resveratrol, including compounds that were devoid of hydroxy groups and were 100-fold more potent than resveratrol. The substituted trans-stilbenes that were potent inhibitors of the activation of NFκB generally did not exhibit antioxidant activity. The results from screening were confirmed using BV-2 microglial cells where resveratrol and analogues were shown to inhibit LPS-induced COX-2 expression.

Co-operative ortho-effects on the Wittig reaction. Interpretation of stereoselectivity in the reaction of ortho-halo-substituted benzaldehydes and benzylidenetriphenylphosphoranes

The E/Z ratios of the stilbenes 1 formed in the Wittig reaction of ortho-halo substituted benzyltriphenylphosphonium salts 2 and benzaldehydes 3 were determined. It was found that there is a co-operative effect of one ortho-halo group on each of the two reacting partners which increases Z-selectivity, but two such groups on the same reactant gives high E-selectivity. The effects are strong enough to be preparatively significant in certain cases and can be interpreted within the modern framework of the Wittig mechanism established by Vedejs and co-workers.