3234-51-3

Usage

Physical state

Colorless liquid 2,2-Dibromocyclopropylbenzene is a liquid that is colorless in appearance.

Aromatic odor

Strong 2,2-Dibromocyclopropylbenzene has a strong, distinctive smell that is characteristic of aromatic compounds.

Primary use

Building block in organic synthesis 2,2-Dibromocyclopropylbenzene is mainly used as a starting material for the synthesis of other organic compounds, providing a foundation for further chemical reactions.

Secondary use

Reagent in organic chemistry 2,2-Dibromocyclopropylbenzene is also used as a reagent to introduce the 2,2-dibromocyclopropyl group into organic molecules, allowing for the creation of new compounds with specific functional groups.

Flammability

Highly flammable Due to its chemical structure, 2,2-Dibromocyclopropylbenzene is prone to catching fire and should be handled with caution.

Health hazards

Skin and eye irritation Contact with 2,2-Dibromocyclopropylbenzene may cause irritation to the skin and eyes, necessitating proper handling and storage procedures to minimize exposure.

Safety precautions

Controlled handling and storage To prevent accidents or harm, it is crucial to handle and store 2,2-Dibromocyclopropylbenzene in a safe and controlled manner, following appropriate guidelines and regulations.

InChI:InChI=1/C9H8Br2/c10-9(11)6-8(9)7-4-2-1-3-5-7/h1-5,8H,6H2

Upstream product

• 100-42-5 styrene 
• 75-25-2 Bromoform 
• 56-23-5 tetrachloromethane 
• 74-95-3 1,1-dibromomethane 
• 558-13-4 carbon tetrabromide 
• 2762-93-8 (1-phenylethane-1,2-diyl)bis(trimethylsilane) 
• 1073-67-2 4-vinylbenzyl chloride 
• 2039-82-9 1-bromo-4-ethenyl-benzene 
• 100-52-7 benzaldehyde 

Downstream Products

• 64286-56-2 1,1-Dibutyl-2-phenylcyclopropan 
• 64286-53-9 (2-butylcyclopropyl)benzene 
• 33450-83-8 trans-1-butyl-2-phenylcyclopropane 
• 7653-94-3 1,1-dimethyl-2-phenylcyclopropane 
• 55027-62-8 trans-1-methyl-2-phenylcyclopropyl bromide 
• 55027-61-7 γ-1-Brom-1-methyl-c-2-phenylcyclopropan 
• 64286-77-7 1-Phenyl-2.2-divinylcyclopropan 
• 66820-54-0 β-bromocinnamyl alcohol 
• 36617-02-4 1-bromo-2-phenylcyclopropane 
• 53783-57-6 2-chloro-3-phenyl-2-propen-1-ol 
• 32523-77-6 trans-1-bromo-2-phenylcyclopropane 
• 55027-68-4 γ-1-Brom-1-ethyl-c-2-phenylcyclopropan 
• 55027-68-4 γ-1-Brom-1-ethyl-t-2-phenylcyclopropan 
• 81391-08-4 2,2-dimethyl-3-phenylcyclobutanone 

Relevant academic research and scientific papers

Photoredox Catalyzed Sulfonylation of Multisubstituted Allenes with Ru(bpy)3Cl2 or Rhodamine B

A highly regio- and stereoselective sulfonylation of allenes was developed that provided direct access to α, β-substituted unsaturated sulfone. By means of visible-light photoredox catalysis, the free radicals produced by p-toluenesulfonic acid reacted with multisubstituted allenes to obtain Markovnikov-type vinyl sulfones with Ru(bpy)3Cl2 or Rhodamine B as photocatalyst. The yield of this reaction could reach up to 91%. A series of unsaturated sulfones would be used for further transformation to some valuable compounds.

Polymerization of Allenes by Using an Iron(II) β-Diketiminate Pre-Catalyst to Generate High Mn Polymers

Herein, we report an iron(II)-catalyzed polymerization of arylallenes. This reaction proceeds rapidly at room temperature in the presence of a hydride co-catalyst to generate polymers of weight up to Mn=189 000 Da. We have determined the polymer structure and chain length for a range of monomers through a combination of NMR, differential scanning calorimetry (DSC) and gel permeation chromatography (GPC) analysis. Mechanistically, we postulate that the co-catalyst does not react to form an iron(II) hydride in situ, but instead the chain growth is proceeding via a reactive Fe(III) species. We have also performed kinetic and isotopic experiments to further our understanding. The formation of a highly unusual 1,3-substituted cyclobutane side-product is also investigated.

Copper(ii)-catalyzed protoboration of allenes in aqueous media and open air

A method has been developed for the facile Cu(ii)-catalyzed protoboration of monosubstituted allenes in aqueous media under atmospheric conditions. The reaction occurs site selectively, favoring internal alkene protoboration to afford 1,1-disubstituted vinylboronic acid derivatives (up to 93?:?7) with modest to good yields. The method has been applied to a variety of phenylallene derivatives as well as alkyl-substituted allenes. This journal is

Enantioselective Addition of α-Nitroesters to Alkynes

By using Rh–H catalysis, we couple α-nitroesters and alkynes to prepare α-amino-acid precursors. This atom-economical strategy generates two contiguous stereocenters, with high enantio- and diastereocontrol. In this transformation, the alkyne undergoes isomerization to generate a RhIII–π-allyl electrophile, which is trapped by an α-nitroester nucleophile. A subsequent reduction with In powder transforms the allylic α-nitroesters to the corresponding α,α-disubstituted α-amino esters.

Photoredox-Catalyzed α-Aminoalkylcarboxylation of Allenes with CO2

The photoredox-catalyzed α-aminoalkylcarboxylation of aryl allenes with CO2 and N,N-dimethylanilines is reported for the first time (26 examples, up to 96% yield). In the case of electron-deficient allenes, good regioselectivity was observed (up to 94:6), exclusively generating kinetic products over thermodynamic products. This protocol is a novel synthetic method for highly functionalized β,γ-unsaturated γ-aminobutyric esters.

Indene formation upon borane-induced cyclization of arylallenes, 1,1-carboboration, and retro-hydroboration

We herein report the reaction of arylallenes with tris(pentafluorophenyl)borane that yields pentafluorophenyl substituted indenes. The tris(pentafluorophenyl)borane induces the cyclization of the allene and transfers a pentafluorophenyl ring in the course of this reaction. A Hammett plot analysis and DFT computations indicate a 1,1-carboboration to be the C-C bond-forming step.

Stereoselective Functionalization of Racemic Cyclopropylzinc Reagents via Enantiodivergent Relay Coupling

Efficient construction of optically pure molecules from readily available starting materials in a simple manner is an ongoing goal in asymmetric synthesis. As a straightforward route, transition-metal-catalyzed enantioconvergent coupling between widely available secondary alkyl electrophiles and organometallic nucleophiles has emerged as a powerful strategy to construct chiral center(s). However, the scope of racemic secondary alkylmetallic nucleophiles for this coupling remains limited in specific substrates because of the difficulties in stereoselective formation of the key alkylmetal intermediates. Here, we report an enantiodivergent strategy to efficiently achieve an array of synthetically useful chiral cyclopropanes, including chiral fluoroalkylated cyclopropanes and enantiomerically enriched cyclopropanes with chiral side chains, from racemic cyclopropylzinc reagents. This strategy relies on a one-pot, two-step enantiodivergent relay coupling process of the racemic cis-cyclopropylzinc reagents with two different electrophiles, which involves kinetic resolution of racemic cis-cyclopropylzinc reagents through a nickel-catalyzed enantioselective coupling with alkyl electrophiles, followed by a stereospecific relay coupling of the remaining enantiomeric cyclopropylzinc reagent with various electrophiles, to produce two types of functionalized chiral cyclopropanes with opposite configurations on the cyclopropane ring. These chiral cyclopropanes are versatile synthons for diverse transformations, rendering this strategy effective for obtaining structurally diversified molecules of medicinal interest.

Diboration of 3-substituted propargylic alcohols using a bimetallic catalyst system: access to (Z)-allyl, vinyldiboronates

The diboration of substituted propargylic alcohols has been achieved using a bimetallic Pd/Cu catalyst system. Thein situformation of a pentrafluoroboronic acid intermediate sufficiently activates the C-O bond towards dual catalysis affording (Z)-allyl, vinyldiboronates stereoselectively.

Intermolecular Allene Functionalization by Silver-Nitrene Catalysis

Under silver catalysis conditions, using [Tp*,BrAg]2 as the catalyst precursor, allenes react with PhI═NTs in the first example of efficient metal-mediated intermolecular nitrene transfer to such substrates. The nature of the substituent at the allene seems crucial for the reaction outcome since arylallenes are converted into azetidine derivatives, whereas methylene aziridines are the products resulting from alkylallenes. Mechanistic studies allow proposing that azetidines are formed through unstable cyclopropylimine intermediates, which further incorporate a second nitrene group, both processes being silver-mediated. Methylene aziridines from alkylallenes derive from catalytic nitrene addition to the allene double bonds. Both routes have resulted to be productive for further synthetic transformations affording aminocyclopropanes.

Formation of Nucleophilic Allylboranes from Molecular Hydrogen and Allenes Catalyzed by a Pyridonate Borane that Displays Frustrated Lewis Pair Reactivity

Here we report the in situ generation of nucleophilic allylboranes from H2 and allenes mediated by a pyridonate borane that displays frustrated-Lewis-pair reactivity. Experimental and computational mechanistic investigations reveal that upon H2 activation, the covalently bound pyridonate substituent becomes a datively bound pyridone ligand. Dissociation of the formed pyridone borane complex liberates Piers borane and enables a hydroboration of the allene. The allylboranes generated in this way are reactive towards nitriles. A catalytic protocol for the formation of allylboranes from H2 and allenes and the allylation of nitriles has been devised. This catalytic reaction is a conceptually new way to use molecular H2 in organic synthesis.