75415-78-0

Basic information

• Product Name: 1,2-Dibromocyclopentene
• Synonyms: 1,2-DIBROMOCYCLOPENTENE;1,2-Dibromocyclopent-1-ene;1,2-Dibromo-1-cyclopentene;1,2-Dibromocyclopentene,97%;1,2-Dibromocyclopent-1-ene 98+%
• CAS NO: 75415-78-0
• Molecular Formula: C₅H₆Br₂
• Molecular Weight: 225.91
• Product Categories: Cycloalkanes;Alkenyl;Halogenated Hydrocarbons;Organic Building Blocks
• Mol File: 75415-78-0.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 78 °C5 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear pale yellow liquid
• Density: 1.895 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.172mmHg at 25°C
• Refractive Index: n20/D 1.5558(lit.)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 1,2-Dibromocyclopentene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Dibromocyclopentene(75415-78-0)
• EPA Substance Registry System: 1,2-Dibromocyclopentene(75415-78-0)

Safety Data

• Hazard Codes: Xi
• WGK Germany: 3
• Hazardous Substances Data: 75415-78-0(Hazardous Substances Data)

Usage

Chemical Properties

Clear pale yellow liquid

Uses

1,2-Dibromocyclopentene has been used in the synthesis of cyclopentene analogs.

General Description

1,2-Dibromocyclopentene undergoes single Br/Mg exchange reaction with iPrMgCl LiCl to yield the corresponding β-bromocyclopentenylmagnesium reagent.

InChI:InChI=1/C5H6Br2/c6-4-2-1-3-5(4)7/h1-3H2

Upstream product

• 89180-82-5 1,2-dibromo-1-chlorocyclopentane 
• 930-29-0 1-chlorocyclopent-1-ene 
• 23586-46-1 1-Lithium-2-brom-cyclopenten-⁽¹⁾ 
• 120-92-3 cyclopentanone 

Downstream Products

• 100393-26-8 2-phenyl-tetrahydro-cyclopenta[c]pyrrole-1,3-dione 
• 136893-23-7 N,N'-diphenyl-cyclopent-1-ene-1,2-dicarboxamide 
• 57669-73-5 2-Phenyl-5,6-dihydro-4H-cyclopenta[c]pyrrole-1,3-dione 
• 136893-24-8 Cyclopent-2-ene-1,2-dicarboxylic acid bis-phenylamide 
• 131496-59-8 1,2-(E,E)-distyrylcyclopentene 
• 400823-13-4 {{2-[(2-bromocyclopent-1-en-1-yl)ethenyl]cyclopent-1-en-1-yl}ethynyl}benzene 
• 400823-17-8 {{2-{{2-[(2-bromocyclopent-1-en-1-yl)ethynyl]cyclopent-1-en-1-yl}ethynyl}cyclopent-1-en-1-yl}ethynyl}benzene 
• 158959-73-0 1-(2-bromocyclopenten-1-yl)-4-(methylsulfonyl)benzene 
• 850864-61-8 2-(2-bromo-cyclopent-1-enyl)-4-chloro-1-methoxy-benzene 
• 400823-15-6 trimethyl{{-{[2-(phenylethynyl)cyclopent-1-en-1-yl]ethynyl}cyclopent-1-en-1-yl}ethynyl}silane 
• 400823-11-2 trimethyl{[2-(phenylethynyl)cyclopent-1-en-1-yl]ethenyl}silane 
• 158959-32-1 1-(2-(4-fluorophenyl)cyclopenten-1-yl)-4-(methylsulfonyl)benzenee 
• 133302-95-1 1-bromo-2-methylcyclopent-1-ene 
• 674798-89-1 1,2-dibenzylcyclopentene 

Relevant articles and documents

The nature of cyclopentyne from different precursors

The ratio of [2+2] and [2+4] cycloaddition products from reaction of spiro[4.2]hepta-1,3-diene with cyclopentyne depends on the source of the cyclopentyne. A mechanistic rationale for the phenomenon is presented.

Photochromic dithienylethenes characterized by: In situ irradiation NMR-spectroscopy and electrochemically induced responsiveness on gold substrates

Photochromic compounds comprising small molecules and polymers have been shown to be of great interest in the field of stimuli-responsive materials for applications as sensors and (nano-) devices. In this regard dithienylethenes (DTEs) have been proven to be especially valuable because of their tolerance to chemicals and their good stability making them tunable and reversibly switchable between an open and a closed structure featuring different optical properties. By utilizing a potent in situ irradiation NMR spectroscopy approach, it is possible to determine the photochromic switching capability of two DTE derivatives in solution leading to crucial information about the structures, the equilibria of the chemical ring-opening and closing of the DTEs as well as the longtime stability of these molecular switches. In particular the perfluorinated thioether bearing compound shows remarkable stability with little fatigue related to the irreversibly cyclized byproduct known for DTEs. The thioether-bearing DTEs can be deprotected and used for immobilization on gold substrates which are characterized by water contact angle measurements prior to and after DTE functionalization. Finally, the electrochemically induced switching capability of the perhydro DTE is investigated by cyclic voltammetry proving its fast, quantitative and reversible cyclization. We envisage these materials for applications as sensors and optical switching devices.

1,2-Diarylcyclopentenes as selective cyclooxygenase-2 inhibitors and orally active anti-inflammatory agents

A series of 1,2-diarylcyclopentene methyl sulfones and sulfonamides have been shown to be remarkably potent and selective cyclooxygenase-2 (COX-2) inhibitors. The methyl sulfone analogs 7 showed excellent COX-2 activity, with IC50s ranging from