4103-11-1

Usage

Uses

Used in Organic Synthesis:
(1E)-1-bromocyclooctene is used as a reagent in organic synthesis for various chemical reactions. Its unique reactivity and the presence of the bromine atom allow it to be a key component in the preparation of other organic compounds.
Used in Pharmaceutical Production:
(1E)-1-bromocyclooctene serves as a starting material in the production of pharmaceuticals. Its versatility in organic synthesis makes it valuable for creating the complex molecular structures required in medicinal chemistry.
Used in Agrochemical Production:
(1E)-1-bromocyclooctene is also utilized as a starting material in the synthesis of agrochemicals, contributing to the development of new pesticides and other agricultural products.
Used in Fine Chemicals Production:
Its applications extend to the production of other fine chemicals, where its unique properties are harnessed to create specialty chemicals for various industries.
Used in Research and Development:
(1E)-1-bromocyclooctene is employed in research and development laboratories due to its ability to undergo a variety of chemical transformations. This makes it an important tool for exploring new reaction pathways and developing innovative synthetic methods in the field of organic chemistry.

Upstream product

• 29974-69-4 1,2-dibromocyclooctane 
• 931-88-4 cis-Cyclooctene 
• 29974-69-4 trans-1,2-dibromocyclooctane 
• 67-64-1 acetone 
• 931-88-4 1,2-cyclooctene 
• 502-49-8 cycloactanone 
• 29974-69-4 trans-1,2- dibromocyclooctane 

Downstream Products

• 505-48-6 octane-1,8-dioic acid 
• 52113-70-9 cyclooct-1-enyl-diphenyl-methanol 
• 18208-81-6 1,2,3,4-tetraphenyl-5,6,7,8,9,10-hexahydrobenzocyclooctene 
• 1781-78-8 cyclooctyne 
• 68629-76-5 5,6,7,8,9,10-Hexahydro-1,4-diphenylcycloocta<1,2-d>pyridazin 
• 448211-45-8 2-(cyclooct-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 15922-51-7 1-benzyl-4,5,6,7,8,9-hexahydro-1H-cycloocta[d][1,2,3]triazole 
• 6038-12-6 cyclooctene-1-carboxaldehyde 
• 4103-09-7 Cyclooct-1-encarbonsaeure 

Relevant academic research and scientific papers

Reactions of Sodium Diisopropylamide: Liquid-Phase and Solid-Liquid Phase-Transfer Catalysis by N, N, N′, N″, N″-Pentamethyldiethylenetriamine

Sodium diisopropylamide (NaDA) in N,N-dimethylethylamine (DMEA) and DMEA-hydrocarbon mixtures with added N,N,N′,N″,N″-pentamethyldiethylenetriamine (PMDTA) reacts with alkyl halides, epoxides, hydrazones, arenes, alkenes, and allyl ethers. Comparisons of PMDTA with N,N,N′,N′-tetramethylethylenediamine (TMEDA) accompanied by detailed rate and computational studies reveal the importance of the trifunctionality and κ2-κ3 hemilability. Rate studies show exclusively monomer-based reactions of 2-bromooctane, cyclooctene oxide, and dimethylresorcinol. Catalysis with 10 mol % PMDTA shows up to >30-fold accelerations (kcat > 300) with no evidence of inhibition over 10 turnovers. Solid-liquid phase-transfer catalysis (SLPTC) is explored as a means to optimize the catalysis as well as explore the merits of heterogeneous reaction conditions.

Covalent Post-assembly Modification Triggers Multiple Structural Transformations of a Tetrazine-Edged Fe4L6 Tetrahedron

Covalent post-assembly modification (PAM) reactions are useful synthetic tools for functionalizing and stabilizing self-assembled metal-organic complexes. Recently, PAM reactions have also been explored as stimuli for triggering supramolecular structural transformations. Herein we demonstrate the use of inverse electron-demand Diels-Alder (IEDDA) PAM reactions to induce supramolecular structural transformations starting from a tetrazine-edged FeII4L6 tetrahedral precursor. Following PAM, this tetrahedron rearranged to form three different architectures depending on the addition of other stimuli: an electron-rich aniline or a templating anion. By tracing the stimulus-response relationships within the system, we deciphered a network of transformations that mapped different combinations of stimuli onto specific transformation products. Given the many functions being developed for self-assembled three-dimensional architectures, this newly established ability to control the interconversion between structures using combinations of different stimulus types may serve as the basis for switching the functions expressed within a system.

Electronic effects versus distortion energies during strain-promoted alkyne-azide cycloadditions: A theoretical tool to predict reaction kinetics

Second-order reaction kinetics of known strain-promoted azide-alkyne cycloaddition (SPAAC) reactions were compared with theoretical data from a range of ab initio methods. This produced both detailed insights into the factors determining the reaction rates and two straightforward theoretical tools that can be used to predict a priori the reaction kinetics of novel cyclooctynes for strain-promoted cycloaddition reactions. Multiple structural and electronic effects contribute to the reactivity of various cyclooctynes. It is therefore hard to relate a physical or electronic property directly and independently to the reactivity of the cyclooctyne. However, we show that Hartree-Fock LUMO energies, which were acquired while calculating activation energies at the MP2 level of theory, correlate with second-order kinetic rate data and are therefore usable for reactivity predictions of cyclooctynes towards azides. Using this correlation, we developed a simple theoretical tool that can be used to predict the reaction kinetics of (novel) cyclooctynes for SPAAC reactions. Activation energies, distortion energies, and TS conformational data were compared in a set of strained cyclooctynes in strain-promoted azide-alkyne cycloaddition (SPAAC) reactions. Only electronic effects could be accurately related to experimental rate data. Copyright

Formation of enehydrazine intermediates through coupling of phenylhydrazines with vinyl halides: Entry into the Fischer indole synthesis

Cut to the chase: Direct formation of an enehydrazine, an intermediate in the classic Fischer indole synthesis, solves the regioselectivity problem associated with indolization. This approach not only achieves selective synthesis of indoles through proper selection of the vinyl halide, but also leads to quick construction of desoxyeseroline and esermethole, as well as the key structural motif in the Akuammiline alkaloid vincorine. Copyright

Pushing the σ-donor strength in iridium pincer complexes: Bis(silylene) and bis(germylene) ligands are stronger donors than bis(phosphorus(III)) ligands

Breaking the donor limits: The remarkable coordination chemistry of ECHE (E=Si, Ge) ligands with Group-9 metals (Ir, Rh) and their application in catalytic C-H borylation of arenes was investigated. The spectroscopic and structural features of the first [ECE] iridium complexes show the stronger σ-donating properties of the divalent Si and Ge pincer ligands compared to analogous PIII-based ligands. Copyright

Clicking 1,2,4,5-tetrazine and cyclooctynes with tunable reaction rates

Substituted tetrazines have been found to undergo facile inverse electron demand Diels-Alder reactions with "tunable" reaction rates.

Reaction rates and mechanisms for radical, photoinitated addition of thiols to alkynes, and implications for thiol-yne photopolymerizations and click reactions

Because of its utility in network polymerization, dendrimer synthesis, and monomer development, the photoinitiated addition of thiols to alkynes has rapidly become an important tool for polymer scientists. Yet, because this chemistry has only recently been applied to cross-linked polymer development, understanding of the nature of how the yne structure affects the reactions and information on the relative reactivities of alkynes bearing various substituents is unavailable as is the relative addition rate of the thiol to the yne as compared to the vinyl sulfide. Herein, the photoinitiated addition of octanethiol to various alkynes is explored. The most rapid addition of thiols to alkynes is that to cyclooctyne, although the resulting vinyl sulfide does not permit subsequent thiol addition. Furthermore, in the absence of radical initiators and light, thiols add spontaneously to cyclooctynes, suggesting limitations to the orthogonality of the strain-promoted copper-less azide, alkyne cycloadditions. In order of decreasing reaction rates, the consecutive addition of two thiols occurs with the aliphatic 1-octyne > propargyl acetate > methyl propargyl ether > 2-octyne. Ethyl propiolate and methyl propargylamine exhibit very small reaction rates with thiols, and no consecutive addition is observed.