60512-56-3

Usage

Uses

Used in Agricultural Industry:
Benzene, 1-(2,2-dibromoethenyl)-4-methylis used as a pesticide and fungicide for controlling pests and fungi that can damage crops. Its application helps protect agricultural yields and maintain crop quality.
Used in Chemical Synthesis:
In the chemical industry, Benzene, 1-(2,2-dibromoethenyl)-4-methylmay also be used as an intermediate in the synthesis of other organic compounds, leveraging its reactive dibromoethenyl group for further chemical reactions.

Upstream product

• 75-25-2 Bromoform 
• 104-87-0 4-methyl-benzaldehyde 
• 104-81-4 4-Methylbenzyl bromide 
• 558-13-4 carbon tetrabromide 
• 52693-87-5 4-methylbenzaldehyde hydrazone 
• 603-35-0 triphenylphosphine 
• 72591-22-1 p-(2,2,2-Tribromaethyl)-toluol 

Downstream Products

• 1866-39-3 4-methylcinnamic acid 
• 866913-73-7 1,5-di-p-tolylpenta-1,4-diyn-3-ol 
• 34793-64-1 1,5-di-(p-methylphenyl)-1,4-pentadiyn-3-one 
• 1429762-68-4 (4-methylstyryl)diphenylphosphine oxide 
• 23901-75-9 (E)-1-(diphenylphosphinyl)-2-(4-methylphenyl)ethene 
• 1429402-63-0 N-((4-methyl)phenylethynyl)-S-methyl-S-phenylsulfoximine 
• 3287-02-3 4-(phenylethynyl)toluene 
• 24785-38-4 1-methoxy-4-[2-(4-methylphenyl)ethynyl]benzene 
• 15795-00-3 1-(4-nitrophenyl)-2-(4-tolyl)acetylene 
• 22666-07-5 di-p-tolylbutadiyne 
• 3038-62-8 4-Methyltolazoline 
• 108030-80-4 2-(4-methylphenyl)pyrazine 
• 622-97-9 1-ethenyl-4-methylbenzene 
• 60655-80-3 (E)-4-methylstyrenyl bromide 

Relevant academic research and scientific papers

Expedient Synthesis of Bridged Bicyclic Nitrogen Scaffolds via Orthogonal Tandem Catalysis

Bridged nitrogen bicyclic skeletons have been accessed via unprecedented site- and diastereoselective orthogonal tandem catalysis from readily accessible reactants in a step economic manner. Directed Pd-catalyzed γ-C(sp3)-H olefination of aminocyclohexane with gem-dibromoalkenes, followed by a consecutive intramolecular Cu-catalyzed amidation of the 1-bromo-1-alkenylated product delivers the interesting normorphan skeleton. The tandem protocol can be applied on substituted aminocyclohexanes and aminoheterocycles, easily providing access to the corresponding substituted, aza- and oxa-analogues. The Cu catalyst of the Ullmann-Goldberg reaction additionally avoids off-cycle Pd catalyst scavenging by alkenylated reaction product. The picolinamide directing group stabilizes the enamine of the 7-alkylidenenormorphan, allowing further product post functionalizations. Without Cu catalyst, regio- and diastereoselective Pd-catalyzed γ-C(sp3)-H olefination is achieved.

Synthesis of 3,4-bis(Butylselanyl)selenophenes and 4-alkoxyselenophenes promoted by oxone

We describe herein an alternative transition-metal-free procedure to access 3,4-bis(butylsela nyl)selenophenes and the so far unprecedented 3-(butylselanyl)-4-alkoxyselenophenes. The protocol involves the 5-endo-dig electrophilic cyclization of 1,3-diynes promoted by electrophilic organosele-nium species, generated in situ through the oxidative cleavage of the Se-Se bond of dibutyl diselenide using Oxone as a green oxidant. The selective formation of the title products was achieved by controlling the solvent identity and the amount of dibutyl diselenide. By using 4.0 equiv of dibutyl diselenide and acetonitrile as solvent at 80?C, four examples of 3,4-bis(butylselanyl)selenophenes were obtained in moderate to good yields (40–78%). When 3.0 equiv of dibutyl diselenide were used, in the presence of aliphatic alcohols as solvent/nucleophiles under reflux, 10 3-(butylselanyl)-4-alkoxyselenophenes were selectively obtained in low to good yields (15–80%).

Synthesis of Chiral Propargylamines, Chiral 1,2-Dihydronaphtho[2,1-b]furans and Naphtho[2,1-b]furans with C-Alkynyl N,N′-di-(tert-butoxycarbonyl)-aminals and β-Naphthols

Chiral phosphoric acid-catalyzed couplings of C-alkynyl N,N′-di-(tert-butoxycarbonyl)-aminals with β-naphthols led to chiral propargylamines in moderate to high yields with high to excellent enantioselectivity, in which the reactions underwent sequential chiral phosphoric acid-catalyzed in situ formation of N-(tert-butoxycarbonyl)-imines (N-Boc-imines) from the aminals, and 1,2-addition of β-naphthols to the N-Boc-imines. Chiral 1,2-dihydronaphtho[2,1-b]furans and naphtho[2,1-b]furans were prepared with satisfactory results when 10 mol% AgOAc and 20 mol% 2,6-lutidine or 1.2 equiv. of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) were added to the resulting chiral propargylamines solution, respectively.

Pd-Catalyzed Indole Synthesis via C-H Activation and Bisamination Sequence with Diaziridinone

This work describes an efficient Pd-catalyzed indole synthesis. A wide variety of indoles can be obtained in good yields from readily available vinyl bromides. The reaction likely proceeds through a sequential aryl C-H activation and bisamination of a resulting pallada(II)cycle with diaziridinone.

N -tert-butyl -2 -phenylindole derivative Preparation method and application

The invention belongs to the technical field of organic synthesis, and particularly relates to N - tert-butyl -2 -phenyl indole derivatives as well as a preparation method and application thereof. The preparation method comprises the following steps: (Z)-1 - bromo -1 - phenyl -2 - styrene derivative, N, N - di-tert-butyl diazepinone, palladium catalyst, monophosphine ligand, hydrocarbon activator, base and first solvent, and N -tert-butyl -2 -aryl indole derivatives which can synthesize substituent type diversity, and the prepared N -tert-butyl -2 -aryl indole derivative can be used for preparing biologically active molecules N -2 .

The hydrodebromination of 1,1-dibromoalkenes via visible light catalysis

Vinyl bromides are versatile synthetic intermediates and widely applied in organic synthesis and pharmaceuticals. Herein, a hydrodebromination reaction of 1,1-dibromoalkenes was established via visible light catalysis. A variety of structurally different vinyl bromides were obtained in moderate to excellent yields.

A Simplified Protocol for the Stereospecific Nickel-Catalyzed C-S Vinylation Using NiX 2 Salts and Alkyl Phosphites

A Ni-catalyzed C-S cross-coupling using only NiI 2 (0.5-2.5 molpercent) and P(O i Pr) 3 (2.0-10.0 molpercent) is reported. Using an air-stable Ni(II) precatalyst, and a cheap and commercially available ligand, a scalable and robust method was developed to cross-couple various thiophenols and styryl bromides, including some sterically encumbered thiols, an α-bromocinnamaldehyde as well as a thiolation-cyclization.

Cs2CO3-Mediated Vicinal Thiosulfonylation of 1,1-Dibromo-1-Alkenes with Thiosulfonates: An Expedient Synthesis of (E)-1,2-Thiosulfonylethenes

A new and highly efficient vicinal thiosulfonylation of 1,1-dibromo-1-alkenes with thiosulfonates in the presence of cesium carbonate has been developed. The metal-free diheterofunctionalization is an operationally simple to access a wide range of (E)-1,2-thiosulfonylethenes (α-aryl-β-thioarylvinyl sulfones) in moderate to high yields with high levels of stereoselectivities. Further, scalable reactions have been demonstrated for this transformation, thus illustrating its efficiency and practicality. (Figure presented.).

Pd-Catalyzed decarboxylative alkynylation of alkynyl carboxylic acids with arylsulfonyl hydrazides via a desulfinative process

In the presence of a Pd(ii)/P-ligand catalytic system, decarboxylative alkynylation of alkynyl carboxylic acids and arylsulfonyl hydrazides by desulfinative coupling could provide aryl alkynes in satisfactory yields by either judiciously selecting palladium catalysts or modulating phosphine ligands under mild conditions. The reported coupling reactions are very practical as they do not require the protection of inert gas or oxygen and are tolerant to many functional groups.

Construction of Phenanthrenes and Chrysenes from β-Bromovinylarenes via Aryne Diels-Alder Reaction/Aromatization

A highly efficient transition-metal-free general method for the synthesis of polycyclic aromatic hydrocarbons like phenanthrenes and chrysenes (and tetraphene) from β-bromovinylarenes and arynes has been developed. The reactions proceed via an aryne Diels-Alder (ADA) reaction, followed by a facile aromatization. This is the first report on direct construction of chrysenes (and tetraphene) using the ADA approach. Unlike the literature method which is limited to only 9/10-substituted derivatives, this method gives access to a wide variety of functionalized phenanthrenes.