4103-12-2

Basic information

• Product Name: Cyclooctene, 5-bromo-
• CAS NO: 4103-12-2
• Molecular Formula: C8H13Br
• Molecular Weight: 189.095
• Mol File: 4103-12-2.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Cyclooctene, 5-bromo-(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclooctene, 5-bromo-(4103-12-2)
• EPA Substance Registry System: Cyclooctene, 5-bromo-(4103-12-2)

Safety Data

• Hazardous Substances Data: 4103-12-2(Hazardous Substances Data)

Usage

General Description

Cyclooctene, 5-bromo- is a chemical compound that consists of a cyclooctene ring with a bromine atom at the 5th carbon position. It is a colorless liquid with a molecular formula of C8H13Br and a molecular weight of 193.09 g/mol. This chemical is mainly used as a building block in organic synthesis, particularly in the production of specialty chemicals and pharmaceuticals. It is also used as a reagent in various chemical reactions, including halogenation and substitution reactions. Additionally, it has been studied for its potential applications in materials science and polymer chemistry. Due to its reactivity and potential health hazards, proper safety precautions should be taken when handling and using cyclooctene, 5-bromo-.

Upstream product

• 1552-12-1 1,5-cis,cis-cyclooctadiene 
• 54529-99-6 5-acetoxy-6-acetoxymercuriacyclo-octene 
• 5259-72-3 cyclo-octa-1,5-diene 

Downstream Products

• 284-20-8 9-oxa-bicyclo[4.2.1]nonane 
• 281-05-0 9-oxabicyclo[3.3.1]nonane 
• 69492-24-6 8,9-dioxa-bicyclo[5.2.1]decane 
• 65651-41-4 9,10-dioxabicyclo<3.3.2>decane 
• 1552-12-1 1,5-cis,cis-cyclooctadiene 
• 1073-07-0 1,4-cyclooctadiene 
• 4103-10-0 cyclooct-4-ene-1-carboxylic acid 
• 32654-27-6 2-Bromo-9-oxa-bicyclo[3.3.1]nonane 
• 1556-09-8 cyclooctyl bromide 
• 32654-19-6 2-bromo-9-oxabicyclo<4.2.1>nonane 
• 23418-82-8 cis-1,5-cyclooctanediol 
• 52965-57-8 7,8-dioxa-bicyclo[4.2.2]decane 
• 37996-41-1 9-oxabicyclo[3.3.1]nonan-1-ol 

Relevant articles and documents

Cationic Metallo-Polyelectrolytes for Robust Alkaline Anion-Exchange Membranes

Chemically inert, mechanically tough, cationic metallo-polyelectrolytes were conceptualized and designed as durable anion-exchange membranes (AEMs). Ring-opening metathesis polymerization (ROMP) of cobaltocenium-containing cyclooctene with triazole as the only linker group, followed by backbone hydrogenation, led to a new class of AEMs with a polyethylene-like framework and alkaline-stable cobaltocenium cation for ion transport. These AEMs exhibited excellent thermal, chemical and mechanical stability, as well as high ion conductivity.

Ring-opening metathesis polymerization with the second generation hoveyda-grubbs catalyst: An efficient approach toward high-purity functionalized macrocyclic oligo(cyclooctene)s

Herein, we present a facile and general strategy to prepare functionalized macrocyclic oligo(cyclooctene)s (cOCOEs) in high purity and high yield by exploiting the ring-opening metathesis polymerization (ROMP) intramolecular backbiting process with the commercially available second generation Hoveyda-Grubbs (HG2) catalyst. In the first instance, ROMP of 5-acetyloxycyclooct-1-ene (ACOE) followed by efficient quenching and removal of the catalyst using an isocyanide derivative afforded macrocyclic oligo(5-acetyloxycyclooct-1-ene) (cOACOE) in high yield (95%), with a weight-average molecular weight (Mw) of 1.6 kDa and polydispersity index (PDI) of 1.6, as determined by gel permeation chromatography (GPC). The structure and purity of the macrocycles were confirmed by NMR spectroscopy and elemental analysis, which indicated the complete absence of end-groups. This was further supported by GPC-matrix assisted laser desorption ionization time-of-flight mass spectroscopy (GPC-MALDI ToF MS), which revealed the exclusive formation of macrocyclic derivatives composed of up to 45 repeat units. Complete removal of residual ruthenium from the macrocycles was confirmed by inductively coupled plasma atomic emission spectroscopy (ICP-AES). The same methodology was subsequently extended to the ROMP of 5-bromocyclooct-1-ene and 1,5-cyclooctadiene to prepare their macrocyclic derivatives, which were further derivatized to produce a library of functionalized macrocyclic oligo(cyclooctene)s. A comparative study using the second and third generation Grubbs catalysts in place of the HG2 catalyst for the polymerization of ACOE provided macrocycles contaminated with linear species, thus indicating that the bidendate benzylidene ligand of the Hoveyda-Grubbs catalyst plays an important role in the observed product distributions.