5415-82-7

Usage

Explanation

The compound consists of 18 carbon atoms, 16 hydrogen atoms, and 2 bromine atoms.

Explanation

The compound is derived from benzene, with two bromine atoms attached to the 1 and 4 positions, and a butadiene chain connected to the 4-position.

Explanation

It belongs to the class of styrene compounds, which have bromine atoms as substituents.

Explanation

The compound is commonly used as a reagent in various fields, including organic synthesis, chemical research, and the development of pharmaceuticals, agrochemicals, and materials.

Explanation

The compound's chemical properties are influenced by its halogenated aromatic structure and the presence of a conjugated diene system.

Explanation

The compound's structure and properties make it a valuable subject for research and understanding the behavior of similar compounds in the field of organic chemistry.

Structure

Benzene derivative with two bromine atoms and a butadiene chain

Class

Styrene with bromine substituents

Applications

Organic synthesis, chemical research, pharmaceuticals, agrochemicals, and materials science

Chemical properties

Halogenated aromatic compound and conjugated diene

Importance

Understanding and studying the behavior of halogenated aromatic compounds and conjugated dienes in organic chemistry

Upstream product

• 6888-79-5 4-bromo-α-methylstyrene 
• 5391-88-8 1-(4-bromophenyl)ethanol 
• 1122-91-4 4-bromo-benzaldehyde 
• 98-10-2 benzenesulfonamide 
• 2039-82-9 1-bromo-4-ethenyl-benzene 
• 99-90-1 para-bromoacetophenone 

Relevant academic research and scientific papers

Dehydrative Coupling of Benzylic Alcohols Catalyzed by Br?nsted Acid/Lewis Base

Traditional cross-coupling reactions show some disadvantages like the use of organohalides or the production of stoichiometric amounts of waste. The dehydrative homo- or heterocoupling of alcohols therefore arises as an interesting approach for a highly atom-economical formation of carbon–carbon bonds, since water is produced as the only by-product. We herein report a simple and direct, metal-free protocol for the synthesis of olefins by applying catalytic amounts of a sulfonic acid and triphenylphosphane under air. A variety of olefins could be synthesized from benzylic alcohols under relatively mild conditions. Additionally, dehydrative hydroarylation of benzylic alcohols with electron-rich arenes was possible by using only Br?nsted acid under otherwise same reaction conditions. We could show that phosphane additives are essential to overcome oligomerization as main side reaction by the occupancy of the reactive carbocation intermediate.

Transition-Metal-Free Sulfuration/Annulation of Alkenes: Economical Access to Thiophenes Enabled by the Cleavage of Multiple C-H Bonds

A novel, atom economical, and transition-metal-free strategy for the synthesis of thiophenes from substituted buta-1-enes with potassium sulfide has been presented. The reaction achieves double C-S bond formations via cleavage of multiple C-H bonds and provides an efficient approach to access various functionalized thiophenes. Moreover, the strategy can also be used for the synthesis of thiophenes from 1,4-diaryl-1,3-dienes. Mechanistically, DMSO plays a role of oxidant and S3?- in situ generated from K2S is involved.

One-pot synthesis of 1,3-diaryl but-1-enes from 1-arylethanols over Snβ zeolite

An environmentally benign catalytic protocol has been successfully developed for the one-pot synthesis of 1,3-diaryl but-1-enes from 1-arylethanols via dehydration of 1-arylethanols followed by head-to-tail dimerization of vinylarenes over heterogeneous c

Highly efficient TfOH-catalyzed head-to-tail dimerization of vinylarenes

A convenient and efficient TfOH-catalyzed head-to-tail dimerization of vinylarenes has been realized under mild conditions. The present protocol provides an attractive approach to a diverse range of higher olefins in good to excellent yields.

Efficient hydroarylation and hydroalkenylation of vinylarenes by Br?nsted acid catalysis

Br?nsted acid Tf2NH alone catalyzed Friedel-Crafts-type hydroarylation and head-to-tail hydroalkenylation of vinylarenes under mild reaction conditions have been realized, providing a readily scalable, metal-free, and practical access to the 1,1-diarylalkane scaffolds and trans-1,3-diaryl-1-butenes in high yields and excellent regioselectivities.

Iodine-Promoted Metal-Free Head-to-Tail Dimerization of Styrenes Affording 1,3-Diarylbut-1-enes

A convenient and efficient iodine-mediated head-to-tail dimerization of styrenes to produce the corresponding dimers in the presence of triethyl phosphite is reported. The advantages of the present protocol are metal-free conditions, short reaction time, simplicity, and high efficiency.

Calcium(II) catalyzed regioselective dehydrative cross-coupling reactions: Practical synthesis of internal alkenes and benzopyrans

A simple and operationally easy protocol for the regioselective synthesis of internal alkenes through a dehydrative cross-coupling and direct coupling procedure has been described using the environmentally benign Ca(II) catalyst. Several alkenes and alcohols underwent the coupling reaction under solvent-free conditions in a short time to produce the desired alkenes. This method is further extended to show the application in the synthesis of novel benzopyran molecules through a cascade strategy.

Chemoselective hydroamination of vinyl arenes catalyzed by an NHC-amidate-alkoxide Pd(II) complex and p-TsOH

The hydroamination of various substituted vinyl arenes with benzenesulfonamide was explored using an NHC-amidate-alkoxide palladium catalyst in conjunction with p-TsOH. Utilizing halide-substituted and electron-rich vinyl arenes, this methodology selectively furnished the cross-coupled hydroamination products in moderate to excellent yields in a Markovnikov fashion while greatly reducing undesired acid-catalyzed homocoupling of the vinyl arenes. Electron-rich vinyl arenes typically required milder conditions than electron-poor ones. While most effective for para-substituted substrates, the catalyst system also furnished the desired products from ortho- and meta-substituted vinyl arenes with high chemoselectivities.

Highly efficient catalytic dimerization of styrenes via cationic Palladium(II) complexes

A highly efficient head-to-tail dimerization of a styrene was developed using a cationic palladium(II)-catalyzed selective C-C bond forming reaction. The complex [AllylPd(PPh3)]+OTf-, which is believed to generate 'palladium hydride' (Pd-H), catalyzed the dimerization of various styrenes in excellent yields as single isomers. This Pd(II)-catalyzed reaction provides a new economical C-C bond forming method. Copyright

Highly efficient Pd(acac)2/TFA catalyzed head-to-tail dimerization of vinylarenes at room temperature

Pd(acac)2 catalyzed dimerization of vinylarenes to form dimers under mild condition with excellent yields and stereoselectivities. In particular, the use of TFA highly promoted the activity and selectivity of the dimerization. The studies on mechanism for the reaction displayed clearly that the dimerization of styrenes is 100% atom economic reaction.