89619-10-3

Usage

Uses

Used in Organic Synthesis:
1-(1-Bromovinyl)-4-chlorobenzene, 90% is used as a building block in organic synthesis for the production of various other chemical compounds. Its unique structure with a bromine atom, vinyl group, and chlorine substituent allows it to be a versatile component in creating a range of different organic molecules.
Used in Chemical Production:
In the chemical production industry, 1-(1-Bromovinyl)-4-chlorobenzene, 90% serves as an important intermediate in the synthesis of various chemicals. Its presence in the production process can lead to the development of new compounds with specific properties and applications, making it a valuable asset in the chemical manufacturing sector.

InChI:InChI=1/C8H6BrCl/c1-6(9)7-2-4-8(10)5-3-7/h2-5H,1H2

Upstream product

• 873-73-4 4-n-chlorophenylacetylene 
• 187409-10-5 3-chloro-α,β-dibromoethylbenzene 
• 74-95-3 1,1-dibromomethane 
• 1073-67-2 4-vinylbenzyl chloride 
• 23135-16-2 1,2-dibromo-1-(4-chlorophenyl)ethane 
• 99-91-2 para-chloroacetophenone 
• 75230-50-1 p-chloroacetophenone tosylhydrazone 

Downstream Products

• 45941-96-6 2-(4-chlorophenyl)-3-hydroxypropene 
• 89619-01-2 3-(4-chlorophenyl)-1,1,1-trifluorobut-3-en-2-ol 
• 75416-78-3 4,4'-(buta-1,3-diene-2,3-diyl)bis(chlorobenzene) 
• 10425-97-5 6-chloro-2-(4-chlorophenyl)-3-methyl-1H-indene 
• 14804-61-6 1-(1-bromoethyl)-4-chlorobenzene 
• 115982-38-2 1-Chloro-4-(2-methyl-1-methylene-butyl)-benzene 
• 1009-33-2 1-(1-cyclopropylvinyl)-4-chlorobenzene 
• 1596349-44-8 C₂₁H₁₅Cl 
• 536-38-9 4-chlorobenzoylmethyl bromide 

Relevant academic research and scientific papers

Absence of Intermediates in the BINOL-Derived Mg(II)/Phosphate-Catalyzed Desymmetrizative Ring Expansion of 1-Vinylcyclobutanols

The catalyzed desymmetrizative ring expansion of alkenylcyclobutanols promoted by halofunctionalization of the alkene moiety with N-bromosuccinimide has been experimentally and computationally studied. The reaction yields highly enantioenriched cyclopenta

Catalytic Asymmetric Halogenation/Semipinacol Rearrangement of 3-Hydroxyl-3-vinyl Oxindoles: A Stereodivergent Kinetic Resolution Process

A highly enantioselective halogenation/semipinacol rearrangement of isatin-derived allylic alcohols has been developed with a chiral N,N′-dioxide/ScIII complex as catalyst. This strategy involved a pivotal stereodivergent kinetic resolution process and provided a facile and efficient entry to optically active halo-substituted quinolone derivatives and quinoline alkaloids with a quaternary stereocenter simultaneously under mild reaction conditions. Based on the control experiments together with kinetic studies and DFT calculations, a possible catalytic cycle was proposed to illustrate the reaction process and enantiocontrol.

The intramolecular reaction of acetophenoneN-tosylhydrazone and vinyl: Br?nsted acid-promoted cationic cyclization toward polysubstituted indenes

In the presence of TsNHNH2, a Br?nsted acid-promoted intramolecular cyclization ofo-(1-arylvinyl) acetophenone derivatives was developed, leading to polysubstituted indenes with complexity and diversity in moderate to excellent yields. In sharp contrast with either the radical or carbene involved cyclization of aldehydicN-tosylhydrazone with vinyl, a cationic cyclization pathway was involved, whereN-tosylhydrazone served as an electrophile and alkylation reagent during this transformation.

Synthesis of Unsymmetrical 1,4-Dicarbonyl Compounds by Photocatalytic Oxidative Radical Additions

Herein we report a photocatalytic oxidative radical addition reaction for the synthesis of unsymmetrical 1,4-dicarbonyl compounds. This reaction utilizes a desulfurization process to generate electrophilic radicals, which add to α-halogenated alkenes and undergo further oxidation to deliver 1,4-dicarbonyl compounds. This mild and highly efficient method provides a valuable alternative to known strategies.

Electrochemical Semipinacol Rearrangements of Allylic Alcohols: Construction of All-Carbon Quaternary Stereocenters

The first examples of electrochemical trifluoromethylation and sulfonylation/semipinacol rearrangements of allylic alcohols were developed using cheap and stable RSO2Na (R = CF3, Ph) as reagents. Various β-trifluoromethyl and sulfonated ketones were obtained in moderate to excellent yields. This strategy provides a facile, direct, and complementary approach to construct all-carbon quaternary stereocenters. In addition, the reaction has the advantages of being chemical oxidant-free and metal-free and has safe and mild reaction conditions.

Selective Aerobic Oxygenation of Tertiary Allylic Alcohols with Molecular Oxygen

Aerobic epoxidation of tertiary allylic alcohols remains a significant challenge. Reported here is an efficient and highly chemoselective copper-catalyzed epoxidation and semipinacol rearrangement reaction of tertiary allylic alcohols with molecular oxygen. The solvent 1,4-dioxane activates dioxygen, thereby precluding the addition of a sacrificial reductant.

Why is cis/trans stereoinversion with Li+(THF)4 migration across the phenyl ring of α-lithiostyrene accelerated by two ortho-methyl groups?

Common wisdom might anticipate that two methyl groups placed on a molecular migration route should act as an impediment. However, the “conducted tour” migration of Li+(THF)4 across the aryl ring (“π-route”) during the cis/trans stereoinversion of α-arylvinyllithiums had been found to occur with practically equal velocities in the presence of either one or two ortho-alkyl substituents. We now report that the omission of both ortho-methyl groups retards the stereoinversion process. In order to arrive at an answer to the title question, we investigate the aggregation equilibria and microsolvation states of ortho, ortho′-unsubstituted α-lithiostyrenes by means of approved secondary NMR criteria. Beyond such necessary knowledge about the ground-state properties, we provide kinetic evidence showing that the retarded cis/trans stereoinversion of α-lithiostyrene proceeds by the pseudomonomolecular, ionic mechanism with Li+(THF)4 migration.

Electrophilic Trifluoromethylthiolation/Semipinacol Rearrangement: Preparation of β-SCF3 Carbonyl Compounds with α-Quaternary Carbon Center

A new and modular electrophilic trifluoromethylthiolation/semipinacol rearrangement of allylic silyl ethers has been developed under mild conditions. This approach allows the formation of a number of β-SCF3 carbonyl compounds with a cyclic and all-carbon quaternary center framework in moderate to good yields. It should be noted that this achievement is a metal-free process and just requires the use of simple acetyl chloride as an acidic promoter. Additionally, an interesting H-migration in competition with aryl-migration process was revealed.

Cyclic Hypervalent Iodine Reagents for Azidation: Safer Reagents and Photoredox-Catalyzed Ring Expansion

Azides are building blocks of increasing importance in synthetic chemistry, chemical biology, and materials science. Azidobenziodoxolone (ABX, Zhdankin reagent) is a valuable azide source, but its safety profile has not been thoroughly established. Herein, we report a safety study of ABX, which shows its hazardous nature. We introduce two derivatives, tBu-ABX and ABZ (azidobenziodazolone), with a better safety profile, and use them in established photoredox- and metal-mediated azidations, and in a new ring-expansion of silylated cyclobutanols to give azidated cyclopentanones.

Intermolecular Carboamination of Unactivated Alkenes

Herein, we report the first example of group transfer radical addition of O-vinylhydroxylamine derivatives onto unactivated alkenes. By utilizing O-vinylhydroxylamine derivatives as both the N- and C-donors, this reaction enables intermolecular carboamination of unactivated alkenes in an atom economical fashion. As the process is initiated through N-radical addition followed by C-transfer, linear carboamination products are afforded. This differs from canonical radical carbofunctionalization of olefins, which typically favors branched product owing to initiation by C-radical addition.