89220-51-9

Usage

Chemical structure

1-(1-Bromomethyl-vinyl)-4-chloro-benzene consists of a benzene ring with a chlorine atom at the 4th position and a bromomethyl-vinyl group attached to the 1st position.

Bromomethyl-vinyl group

This group consists of a bromine atom bonded to a carbon, which is further bonded to a vinyl group, making it a halogenated alkene.

Halogenated alkene

The presence of a bromine atom in the vinyl group classifies the compound as a halogenated alkene.

Reactivity

The compound has a reactive vinyl group, which allows it to be used as a reagent in various chemical reactions.

Applications

It is commonly used in organic synthesis and can be used as a building block in the synthesis of more complex organic molecules.

Hazardous nature

The compound is potentially hazardous and should be handled with caution.

Controlled environment

It should be used in a controlled environment by trained professionals to ensure safety and proper handling.

Upstream product

• 1712-70-5 1-chloro-4-(1-methylethenyl)-benzene 
• 7732-18-5 water 
• 45941-96-6 2-(4-chlorophenyl)-3-hydroxypropene 
• 106-39-8 bromochlorobenzene 
• 99-91-2 para-chloroacetophenone 

Downstream Products

• 145949-83-3 N-<2-(4-chlorophenyl)prop-2-enyl>phthalimide 
• 843651-74-1 N-tert-butoxycarbonyl-N'-[2-(4-chlorophenyl)allyl]hydrazine 
• 897019-27-1 tert-butyl 4-(2-(4-chlorophenyl)prop-2-en-1-yl)piperazine-1-carboxylate 
• 1191271-44-9 2-[2-(4-chloro-phenyl)-allyloxy]-naphthalene-1-carbaldehyde 
• 1447974-53-9 tert-butyl (2-(4-chlorophenyl)allyl)carbamate 
• 1447974-62-0 5-(chloromethyl)-5-(4-chlorophenyl)oxazolidin-2-one 
• 1447974-71-1 5-(chloromethyl)-5-(4-chlorophenyl)oxazolidin-2-one 
• 81187-88-4 3-(4-chlorophenyl)-3-butenoic acid 
• 1415643-30-9 1-methyl-4-((2-(4-chlorophenyl)allyl)sulfonyl)benzene 

Relevant academic research and scientific papers

Visible-light-promoted radical alkylation/cyclization of allylic amide with N-hydroxyphthalimide ester: Synthesis of oxazolines

An efficient photocatalytic alkylation/cyclization of allylic amide with N-hydroxyphthalimide ester has been developed. The transformation is taken advantage of alkyl radicals to attack allylic amide with the assist of inexpensive rose bengal as photocatalyst to prepare a series of alkyl substituted oxazolines in moderate to excellent yields. High regioselectivity, operational safety, mild conditions and excellent substrate generality give this protocol broad application prospects.

Copper-Catalyzed Enantiotopic-Group-Selective Allylation of gem-Diborylalkanes

We report a copper-catalyzed enatiotopic-group-selective allylation of gem-diborylalkanes with allyl bromides. The combination of copper(I) bromide and H8-BINOL derived phosphoramidite ligand proved to be the most effective catalytic system to provide various enantioenriched homoallylic boronate esters, containing a boron-substituted stereogenic center that is solely derived from gem-diborylalkanes, in good yields with high enantiomeric ratios under mild conditions. Experimental and theoretical studies have been conducted to elucidate the reaction mechanism, revealing how the enatiotopic-group-selective transmetalation of gem-diborylalkanes with chiral copper complex occurs to generate chiral α-borylalkyl-copper species for the first time. Additional synthetic applications to the synthesis of various chiral building blocks are also included.

Synthesis of Six-Membered Spiro Azacyclic Oxindole Derivatives via a One-Pot Process of Umpolung Allylation/Aza-Prins Cyclization

An unprecedented synthetic approach involving umpolung allylation/aza-Prins cyclization of N-2,2,2-trifluoroethylisatin ketimines is described. The reactions proceed smoothly with allyl bromide in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene, H2O, and trimethylsilyl bromide; this one-pot protocol allows access to six-membered spiro azacyclic oxindole derivatives in good to excellent yields. Notably, while the general aza-Prins cyclization involves amines and aldehydes, the present synthetic strategy represents the first aza-Prins cyclization that utilizes the umpolung property of N-2,2,2-trifluoroethylisatin ketimines.

Pd-Catalyzed Asymmetric Acyl-Carbamoylation of an Alkene to Construct an α-Quaternary Chiral Cycloketone

Herein, we report the palladium-catalyzed asymmetric acyl-carbamoylation of an alkene by employing thioesters as the acyl electrophiles and t-BuNC as the carbamoyl reagent, affording an α-quaternary chiral cycloketone in synthetically useful yields with excellent enantioselectivity. The reaction proceeded via asymmetric 1,2-migratory insertions of acyl-Pd into alkenes and subsequent migratory insertion of isocyanides into C(sp3)-PdII. The product could be diversified to some valuable skeletons with retention of enantiopurity, demonstrating the synthetic utility of this protocol.

HETEROAROMATIC COMPOUNDS AS VANIN INHIBITORS

The present invention encompasses compounds of the formula I which are suitable for the treatment of diseases related to Vanin, and processes for making these compounds, pharmaceutical preparations containing these compounds, and their methods of use.

3 -trifluoromethyl -5 - aryl -1, 6 -dihydropyridazine compound and preparation method thereof (by machine translation)

The invention relates to 3 - trifluoromethyl -5 - aryl -1, 6 -dihydropyridazine compound, and the structural formula of the compound is as follows. Ar refers to Ar. . . One of the following. , The invention also discloses a preparation method of the compound. To the invention, the oxidation/cyclization reaction of 4 - aryl substituted trifluoromethylhomoallylhydrazine is promoted by copper acetate, 3 - trifluoromethyl -5 - aryl -1 and 6 -dihydropyridazine compound with obvious aggregation-induced emission effect are obtained. (by machine translation)

Chiral Br?nsted Acid Catalyzed Dynamic Kinetic Asymmetric Hydroamination of Racemic Allenes and Asymmetric Hydroamination of Dienes

The first highly efficient and practical chiral Br?nsted acid catalyzed dynamic kinetic asymmetric hydroamination (DyKAH) of racemic allenes and asymmetric hydroamination of unactivated dienes with both high E/Z selectivity and enantioselectivity are described herein. The transformation proceeds through a new catalytic asymmetric model involving a highly reactive π-allylic carbocationic intermediate, generated from racemic allenes or dienes through a proton transfer mediated by an activating/directing thiourea group. This method affords expedient access to structurally diverse enantioenriched, potentially bioactive alkenyl-containing aza-heterocycles and bicyclic aza-heterocycles.

Highly Enantioselective Iridium-Catalyzed Hydrogenation of 2-Aryl Allyl Phthalimides

The iridium-catalyzed asymmetric hydrogenation of 2-aryl allyl phthalimides to afford enantioenriched β-aryl-β-methyl amines is presented. Recently developed Ir-MaxPHOX catalysts are used for this enantioselective transformation. The mild reaction conditions and the feasible removal of the phthalimido group makes this catalytic method easily scalable and of great interest to afford chiral amines. The importance of this new methodology is exemplified by the formal synthesis of (R)-Lorcaserin, OTS514, and enantiomerically enriched 3-methyl indolines.

Rhodium-Catalyzed Enantioconvergent Isomerization of Homoallylic and Bishomoallylic Secondary Alcohols

We present herein an unprecedented enantioselective isomerization of homoallylic and bishomoallylic secondary alcohols, catalyzed by a commercially available rhodium-complex and a base. This catalytic redox-neutral process provides an effective access to chiral ketones in high efficiency and enantioselectivity, without the use of any stoichiometric reagent or generation of any waste. For the reaction of homoallylic alcohols, this system achieved not only a stereoconvergent access to chiral ketones bearing a β-stereocenter (up to 95%, 86% ee) but also a concomitant oxidative kinetic resolution of the alcohol substrates (S > 20). In the case of bishomoallylic alcohols, an intriguing ligand-induced divergent reactivity was observed. A terminal-to-internal alkene isomerization promoted by Rh/L7 followed by redox isomerization using Rh/BINAP system produced chiral ketones bearing a γ-stereocenter with high yield and enantioselectivity. Mechanistic studies provided strong support for the redox-isomerization pathway with chain walking of the key alkyl-Rh intermediate.

Visible-Light Photocatalytic Bicyclization of 1,7-Enynes toward Functionalized Sulfone-Containing Benzo[a]fluoren-5-ones

A new visible-light photocatalytic arylsulfonylation and bicyclization of C(sp3)-tethered 1,7-enynes with sulfinic acids has been developed, delivering functionalized sulfone-containing benzo[a]fluoren-5-ones with generally good yields. This Eosin Y-catalyzed approach makes use of visible light as a safe and eco-friendly energy source to drive cascade cyclization reactions, resulting in continuous multiple bond-forming events including C–S and C–C bonds to efficiently construct polycyclic-linked alkyl aryl sulfones. (Figure presented.).