20432-10-4

Usage

Uses

Used in Organic Synthesis:
(E)-1,2-Dibromo-1,2-diphenylethene is used as a building block in the organic synthesis industry for the creation of various organic compounds. Its unique structure and reactivity make it a valuable component in the synthesis of complex molecules.
Used in Pharmaceutical Preparation:
In the pharmaceutical industry, (E)-1,2-Dibromo-1,2-diphenylethene is used as a common reagent in the preparation of different pharmaceuticals. Its versatility in chemical reactions allows for the development of a wide range of medicinal compounds.
Used in Agrochemical Production:
(E)-1,2-Dibromo-1,2-diphenylethene also finds application in the agrochemical industry, where it is used in the production of various agrochemicals. Its role in this industry is crucial for the development of effective agricultural products.
Used in Photochemical and Radical Reaction Studies:
In the field of chemical research, (E)-1,2-Dibromo-1,2-diphenylethene is used as a model compound for studying photochemical reactions and radical reactions. Its properties make it an ideal candidate for understanding the underlying mechanisms and kinetics of these types of reactions.
Safety Precautions:
Due to its toxic nature, (E)-1,2-Dibromo-1,2-diphenylethene should be handled with caution. It is essential to follow proper safety protocols to minimize the risk of skin, eye, and respiratory system irritation. Appropriate personal protective equipment (PPE) should be worn, and the compound should be stored and used according to the manufacturer's guidelines.

Upstream product

• 501-65-5 diphenyl acetylene 
• 108-88-3 toluene 
• 2489-03-4 tribromomethylbenzene 
• 4541-89-3 2-chloro-1,1-diphenylethene 
• 15219-34-8 Oxalyl bromide 
• 3469-17-8 2-diazo-1,2-diphenylethan-1-one 
• 67-56-1 methanol 
• 103-29-7 1,1'-(1,2-ethanediyl)bisbenzene 
• 13440-24-9 1,2-dibromo-1,2-diphenylethane 
• 588-59-0 stilbene 
• 79-15-2 N-bromoacetamide 
• 151416-94-3 (Z)-2,2'-[1,2-(biphenyl)eth-1-ene-1,2-diyl]bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) 

Downstream Products

• 1212-08-4 S-Phenyl benzenethiosulfonate 
• 501-65-5 diphenyl acetylene 
• 134-81-6 benzil 
• 98-11-3 benzenesulfonic acid 
• 92-52-4 biphenyl 
• 661-69-8 hexamethyldistannane 
• 16387-72-7 tetradeca-6,8-diyne 
• 882-33-7 diphenyldisulfane 
• 27435-08-1 (E)-bis(trimethylstannyl)stilbene 
• 25044-96-6 bis(triphenylphosphine)palladium dibromide 
• 2450-55-7 diphenyl fumarodinitrile 
• 5088-12-0 acetic acid-(α'-bromo-stilben-α-yl ester) 

Relevant academic research and scientific papers

Graphene nanoribbons from tetraphenylethene-based polymeric precursor: Chemical synthesis and application in thin-film field-effect transistor

Graphene nanoribbons (GNRs) with a non-zero bandgap are regarded as a promising candidate for the fabrication of electronic devices. In this study, large-scale solution synthesis of narrow GNRs was firstly achieved by the intramolecular cyclodehydrogenati

Dehalogenation of vicinal dihalo compounds by 1,1′-bis(trimethylsilyl)-1: H,1′ H-4,4′-bipyridinylidene for giving alkenes and alkynes in a salt-free manner

We report a transition metal-free dehalogenation of vicinal dihalo compounds by 1,1′-bis(trimethylsilyl)-1H,1′H-4,4′-bipyridinylidene (1) under mild conditions, in which trimethylsilyl halide and 4,4′-bipyridine were generated as byproducts. The synthetic protocol for this dehalogenation reaction was effective for a wide scope of dibromo compounds as substrates while keeping the various functional groups intact. Furthermore, the reduction of vicinal dichloro alkanes and vicinal dibromo alkenes also proceeded in a salt-free manner to afford the corresponding alkenes and alkynes.

Ladder-type conjugated oligomers prepared by the Scholl oxidative cyclodehydrogenation reaction: Synthesis, characterization and application in field effect transistors

Two novel well defined ladder-type conjugated oligomers have been successfully designed and synthesized through a solution processing method in an excellent yield. The field effect transistors (FETs) fabricated by these ladder-type oligomers with a nice planar structure exhibit excellent charge carrier mobilities, up to 0.10 cm2 V-1 s-1 and 0.33 cm2 V-1 s-1; furthermore, the devices can work well with a low gate voltage. The ladder-type oligomers are both converted from two precursor co-oligomers, poly(2,7-(1,2,-diphenylethene)-9,9-dioctylfluorene) (PDPF), via an anhydrous FeCl3 oxidative cyclodehydrogenation. The pronounced red shift shown in the preliminary photoluminescence spectra and the changes of band gaps measured by electrochemical analysis both testify that the better electronic transmission capacity in the FET performance is due to the expanded molecular chain planarization after the chemical cyclodehydrogenation. Interestingly, the precursor oligomers having a linear-type chain and a zigzag-type chain (L-PDPF and Z-PDPF, respectively) show many characteristic differences in their thermal, optical and electrochemical properties. The differences caused by the different types of main chains demonstrate that the macromolecular configurations have a tremendous impact on the functioning of the oligomers.

Halodeboronation of organotrifluoroborates using tetrabutylammonium tribromide or cesium triiodide

Halodeboronation of organotrifluoroborates using commercially available tetrabutylammonium tribromide (TBATB) or cesium triiodide in aqueous medium is reported. The mild, transition metal-free method has proven to be tolerant of a wide range of functional groups. High regio- and chemoselectivity are observed. Two synthetic routes to (Z)-dibromoalkenes from alkynes, through stereodefined (Z)-2-bromoalkenyltrifluoroborates and (Z)-1,2-bis(boryl) alkenyltrifluoroborates, have been developed using the TBATB mediated bromodeboronation as the key step.

Sequential bromination reactions from beads with methyltriphenylphosphonium tribromide groups

A reusable bromination reagent based on polystyrene beads with covalently appended methyltriphenylphosphonium tribromide groups has been developed. The results from bromination reactions of several structurally diverse unsaturated substrates with the beads and with solutions of a non-polymeric model brominating reagent, methyltriphenylphosphonium tribromide, are described. It is shown that the reactions are highly regio- and stereo-selective and can be conducted easily. Copyright

Tetraalkylphosphonium trihalides. Room temperature ionic liquids as halogenation reagents

(Chemical Equation Presented) Six room temperature ionic liquids (RTILs) comprised of a tetraalkylphosphonium cation (tridecylmethyphosphonium or trihexyltetradecylphosphonium) and a trihalide anion (Br3 -, BrCl2-, or ClBr2-) have been prepared and characterized. Their ability to effect halogenation reactions with a variety of substrates has been explored. In general, halogenation reactions of alkenes proceed with high yields and stereo- and regioselectivities, whether performed in the absence or presence of a solvent (chloroform). Reactions of an alkyne and electrophilic substitution on an aromatic ring have been investigated as well. The facile preparation of the salts, their ease of handling, and the simplicity of product isolation should make these RTILs useful additions to the repertoire of halogenation reagents and the reagents of choice for specific transformations.

Selective aerobic oxidative dibromination of alkenes with aqueous HBr and sodium nitrite as a catalyst

Various alkenes (internal, terminal, aryl and alkyl substituted) and 1,2-diphenylethyne were efficiently and selectively dibrominated using 2 equivalents of 48% aqueous hydrobromic acid, with air as an oxidant and sodium nitrite as a catalyst. Despite the presence of water, only trans dibromination occurred producing anti-1,2-dibromoalkanes and (E)-1,2-dibromo-1,2- diphenylethene. A comparison of resource demand, waste production and environmental, health and safety issues of the NaNO2 catalyzed aerobic bromination with molecular bromine and other oxidative bromination methods revealed that the proposed method is not only selective and effective but has a better environmental profile.

Stereoselective bromination reactions using tridecylmethylphosphonium tribromide in a "stacked" reactor

(Chemical Equation Presented) A new reagent, tridecylmethylphosphonium tribromide, and new procedures for bromination reactions of unsaturated substrates (including one that allows several substrates to be reacted in sequence) are described. The procedures exploit the diffusion of components and the densities and immiscibilities of layers, including a fluorous "spacer" layer, within a reaction vessel. The stereoselectivities achieved in the reactions are superior in some cases to those found with other brominating reagents.

Mild oxidative bromination of alkenes and alkynes with zinc bromide and lead tetraacetate

Zinc bromide and lead tetraacetate is a practical and safe source of bromine. The combined reagents are used to brominate a variety of alkenes to vicinal dibromoalkanes. Similarly, alkynes can be converted into dibromoalkenes in high yields. The reagents are also capable of tetrabromination of alkynes.

The effect of vicinyl olefinic halogens on cross-coupling reactions using Pd(0) catalysis

(trans) 1-Chloro-2-iodoethylene (3), (trans) 1-bromo-2-iodoethylene (4), (trans) 1,2-diiodoethylene (5) and (cis and trans) 1,2-dibromoethylene (11) were reacted under Suzuki, Sonogashira and Negishi cross-coupling conditions using Pd catalysis to obtain mono coupled products. Only olefin template 3 provided the desired coupling products reliably under all reaction conditions. Compound 5 did not provide cross coupled products under any of the reaction conditions used. The Negishi reaction was the only one that worked for templates 4 and 11. Studies indicate that oxidative addition of the most reactive carbon-halogen bond to Pd(0) is followed by elimination of the second halide, when the second halide is a bromide or an iodide. This happens to a much lesser degree when the second halogen is a chloride. Graphical Abstract.