61815-42-7

Usage

Uses

Used in Organic Synthesis:
(E)-1-Bromo-cyclooctene is used as a building block in the synthesis of complex organic molecules. Its reactivity allows for the creation of a wide range of compounds, making it a versatile component in chemical research and development.
Used in Pharmaceutical Production:
(E)-1-Bromo-cyclooctene is utilized as a reagent in the production of pharmaceuticals. Its ability to undergo halogenation and cross-coupling reactions contributes to the synthesis of various medicinal compounds.
Used in Agrochemicals:
In the agrochemical industry, (E)-1-Bromo-cyclooctene serves as a reagent for the synthesis of chemical compounds used in agriculture, such as pesticides and herbicides.
Used in Fine Chemicals:
(E)-1-Bromo-cyclooctene is also employed in the production of fine chemicals, which are high-purity chemicals used in various industries, including the fragrance, flavor, and specialty chemical sectors.
Safety Precautions:
Due to its flammability and toxicity, (E)-1-Bromo-cyclooctene must be handled with care to ensure safety in the laboratory and industrial settings. Proper safety measures, including the use of protective equipment and adherence to handling protocols, are essential when working with (E)-1-Bromo-cyclooctene.

Upstream product

• 931-88-4 cis-Cyclooctene 
• 1781-78-8 cyclooctyne 
• 34969-65-8 trans-1,2-dibromocyclooctane 
• 18208-83-8 cis-1,2-dibromocyclooctene 
• 30860-01-6 2-Brom-trans-cyclooct-2-enol 
• 931-88-4 1,2-cyclooctene 
• 87635-75-4 (1R,2R)-1-Bromo-2-chloro-cyclooctane 
• 29974-69-4 trans-1,2-dibromocyclooctane 
• 29974-69-4 1,2-dibromocyclooctane 

Downstream Products

• 1781-78-8 cyclooctyne 
• 67788-08-3 (E)-cyclooct-1-en-1-yl(phenyl)methanone 
• 96308-48-4 cyclooctene-1-carbaldehyde 
• 67788-06-1 Bis(1-cyclooctenyl)phenylmethanol 
• 18292-62-1 cyclooct-1c-enecarboxylic acid 
• 62995-25-9 (E)-methyl cyclooct-1-enecarboxylate 
• 137407-47-7 (E)-1-phenylcyclooctene 
• 124286-31-3 1-Acetylcyclooctene tosylhydrazone 
• 935-29-5 1,3-cyclooctanedione 
• 100-66-3 methoxybenzene 
• 579-75-9 2-Methoxybenzoic acid 
• 933-11-9 methylcyclooctene 
• 67788-05-0 (+/-)-cyclooct-1c-enyl-phenyl-methanol 

Relevant academic research and scientific papers

One-pot synthesis of substituted styrenes from vicinal dibromoalkanes and arylboronic acids

Dehydrobromination of vicinal dibromoalkanes in systems comprising 1,2-dimethoxy-ethane, N-butyl-N′-methylimidazolium tetrafluoroborate (or tetrabutylammonium bromide), and a base with subsequent palladium-catalyzed cross-coupling of the thus formed bromoalkenes with arylboronic acids furnished substituted styrenes. Springer Science+Business Media, Inc. 2007.

Efficient Synthesis of Amines by Iron-Catalyzed C=N Transfer Hydrogenation and C=O Reductive Amination

Here we report the catalytic transfer hydrogenation (CTH) of non-activated imines promoted by a Fe-catalyst in the absence of Lewis acid co-catalysts. Use of the (cyclopentadienone)iron complex 1, which is much more active than the classical ‘Kn?lker complex’ 2, allowed to reduce a number of N-aryl and N-alkyl imines in very good yields using iPrOH as hydrogen source. The reaction proceeds with relatively low catalyst loading (0.5–2 mol%) and, remarkably, its scope includes also ketimines, whose reduction with a Fe-complex as the only catalyst has little precedents. Based on this methodology, we developed a one-pot CTH protocol for the reductive amination of aldehydes/ketones, which provides access to secondary amines in high yield without the need to isolate imine intermediates. (Figure presented.).

Engaging Alkenyl Halides with Alkylsilicates via Photoredox Dual Catalysis

Single-electron transmetalation via photoredox/nickel dual catalysis provides the opportunity for the construction of Csp3-Csp2 bonds through the transfer of alkyl radicals under very mild reaction conditions. A general procedure for the cross-coupling of primary and secondary (bis-catecholato)alkylsilicates with alkenyl halides is presented. The developed method allows not only alkenyl bromides and iodides but also previously underexplored alkenyl chlorides to be employed. (Chemical Equation Presented).

Organic photoredox catalysis for the oxidation of silicates: Applications in radical synthesis and dual catalysis

Metal free photooxidation of alkyl bis(catecholato)silicates with the organic dye 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyano-benzene (4CzIPN) allows the smooth formation of alkyl radicals. The latter can be efficiently engaged either with radical acceptors to provide homolytic addition products or in photoredox/nickel dual catalysis reactions to obtain cross-coupling products.

Efficient synthesis of bicyclo[6.3.0]undecadienones by Nazarov cyclization/regioselective elimination

Easily accessible cyclooctadienyl vinyl ketones can generate fused bicyclic 8-5 (bicyclo[6.3.0]undecadienone) ring systems via the Nazarov cyclization when treated with Lewis acid. The resultant products contain three new stereocenters as well as olefins suitably situated to allow further structural elaboration. This concise sequence allows for the rapid preparation of intermediates that should be applicable to a variety of natural product targets containing this bicyclic core.

Regio- and stereoselectivity of ene eeactions: The dimerization of bicyclic 1,3-fused 2-(trimethylsilyl)cycloprop-1-enes

Cycloalkenes proceed through bromination, dehydrobromination and dibromocarbene addition reactions to give tribromocyclopropanes 10 and 11. The treatment of tribromocyclopropanes 10 and 11 with 3 equiv. of methyllithium in diethyl ether at -78°C followed by treatment with trimethylsilyl chloride produce 8-(trimethylsilyl)bicyclo[5.1.0]oct-1(8)-ene (4) and 9-(trimethylsilyl)bicyclo[6.1.0]non-1(9)-ene (5). Both 4 and 5 undergo ene dimerization via the same steric isomer and an endo transition state to generate the stable adducts 6 and 7, respectively, as the sole isomers. Compound 6, containing an unstable bicyclo[5.1.0]oct-1(8)-enyl group and produced in high yields, has been reported to be an unstable species. Both of the ene dimers, (trimethylsilyl)cyclopropenes 6 and 7, can be converted into cyclopropenes 8 and 9 by treatment with a fluoride salt followed by protonation. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

cis-bromination of alkynes without cationic intermediates

Surprising insight into a classical mechanism is provided by theoretical and experimental investigations on the bromination of alkynes. in nonpolar solvents the bromination of acetylene via a covalent tribromide adduct is strongly favored over the textbook mechanism via a bridged bromirenium ion. The structurally interesting intermediate explains the syn selectivity of the bromination of strained cycloalkynes.

A Simple Preparation of Cyclic Vinylic Bromides (1-Bromocycloalkenes and 1-Bromo-1,5-cyclooctadiene) from 1,2-Dibromocycloalkanes

1,2-Dibromocyclopentane, 1,2-dibromocyclohexane, 1,2-dibromocycloheptane, 1,2-dibromocyclooctane, 1,2-dibromocyclododecane, and 5,6-dibromocyclooctene are smoothly dehydrobrominated to the corresponding 1-bromocycloalkenes in good yield using morpholine and dimethyl sulfoxide in benzene or ethanol.

COMPARISON OF SYN DEHYDROHALOGENATIONS FROM TANS-1-BROMO-2-CHLOROCYCLOALKENES PROMOTED BY COMPLEX BASE AND BY POTASSIUM TERT-BUTOXIDE

Compared with t-BuOK-t-BuOH, syn eliminations from trans-1-bromo-2-chlorocycloalkanes (C4-C8) induced by NaNH2-NaO-t-Bu in THF are rapid, exhibit greater propensity for dehydrochlorination and show little sensitivity to ring size of the dihalocycloalkane.