3234-51-3

Basic information

• Product Name: 2,2-Dibromocyclopropylbenzene
• Synonyms: 1-(Phenyl)-2,2-dibromocyclopropane;2,2-Dibromocyclopropylbenzene
• CAS NO: 3234-51-3
• Molecular Formula: C₉H₈Br₂
• Molecular Weight: 275.96782
• Mol File: 3234-51-3.mol
• Article Data: 52

Chemical Properties

• Boiling Point: 282.2°C at 760 mmHg
• Flash Point: 141.2°C
• Appearance: /
• Density: 1.908g/cm³
• Vapor Pressure: 0.00581mmHg at 25°C
• Refractive Index: 1.666
• CAS DataBase Reference: 2,2-Dibromocyclopropylbenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-Dibromocyclopropylbenzene(3234-51-3)
• EPA Substance Registry System: 2,2-Dibromocyclopropylbenzene(3234-51-3)

Safety Data

• Hazardous Substances Data: 3234-51-3(Hazardous Substances Data)

Usage

Physical state

Colorless liquid This compound 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 This compound 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 
• 558-13-4 carbon tetrabromide 
• 2039-82-9 1-bromo-4-ethenyl-benzene 
• 1073-67-2 4-vinylbenzyl chloride 
• 2762-93-8 (1-phenylethane-1,2-diyl)bis(trimethylsilane) 
• 100-52-7 benzaldehyde 
• 74-95-3 1,1-dibromomethane 

Downstream Products

• 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 
• 1145-92-2 (1SR,2SR)-phenyl(2-phenylcyclopropyl)ketone 
• 1145-91-1 cis-(2-phenylcyclopropyl)(phenyl)methanone 
• 18523-34-7 1,1-dimethoxy-2-phenylcyclopropane 
• 144482-64-4 ((Z)-2-Bromo-3-methoxy-propenyl)-benzene 
• 51493-79-9 (2-Bromo-1-methoxy-allyl)-benzene 
• 104-51-8 1-butylbenzene 

Relevant articles and documents

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.

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.