53155-11-6

Usage

Uses

Used in Pharmaceutical Industry:
(Z)-1-Bromo-3-octene is used as a synthetic intermediate for the production of various pharmaceuticals. Its unique structure and reactivity allow for the creation of a wide range of medicinal compounds, contributing to the development of new drugs and therapies.
Used in Agrochemical Industry:
In the agrochemical sector, (Z)-1-Bromo-3-octene serves as a key intermediate in the synthesis of various agrochemicals. Its incorporation into these products aids in enhancing their effectiveness and performance, supporting agricultural productivity and crop protection.
Used in Fine Chemicals Manufacturing:
(Z)-1-Bromo-3-octene is also utilized in the manufacturing of fine chemicals. Its unique properties make it an essential component in the production of specialty chemicals that have specific applications in various industries, including cosmetics, fragrances, and flavorings.
Used in Organic Synthesis Research:
As a building block in the synthesis of complex organic molecules, (Z)-1-Bromo-3-octene plays a crucial role in advancing chemical research. Its versatility and reactivity enable scientists to explore new pathways and develop innovative compounds with potential applications in various fields.

InChI:InChI=1/C8H15Br/c1-2-3-4-5-6-7-8-9/h5-6H,2-4,7-8H2,1H3/b6-5-

Upstream product

• 18185-81-4 cis-3-octen-1-ol 
• 288591-17-3 (Z)-oct-3-enyl methanesulfonate 
• 693-02-7 hex-1-yne 
• 14916-80-4 oct-3-yn-1-ol 
• 85217-50-1 2-(3-octyn-1-yloxy)tetrahydro-2H-pyran 
• 160436-23-7 (Z)-2-(3-octen-1-yloxy)tetrahydro-2H-pyran 
• 111789-39-0 (Z)-oct-3-enyl 4-methylbenzenesulfonate 

Downstream Products

• 69668-83-3 (3Z)?3-octenyl acetate 
• 18185-81-4 cis-3-octen-1-ol 
• 16725-53-4 (Z)-9-tetradecen-1-yl acetate 
• 35153-15-2 (Z)-9-tetradecen-1-ol 
• 71612-09-4 (Z)-1-(2-Tetrahydropyranyloxy)-9-tetradecene 
• 53963-06-7 Z,Z-7,11-hexadecadienyl alcohol 
• 52207-99-5 (7Z,11Z)-7,11-hexadecadien-1-yl acetate 

Relevant academic research and scientific papers

Natural trienoic acids as anticancer agents: First stereoselective synthesis, cell cycle analysis, induction of apoptosis, cell signaling and mitochondrial targeting studies

The first Z-stereoselective method was developed for the synthesis of unsaturated acids containing a 1Z,5Z,9Z-triene moiety in 61–64% yields using the new Ti-catalyzed cross-coupling of oxygen-containing and aliphatic 1,2-dienes as the key synthetic step. It was shown for the first time that trienoic acids with non-methylene-interrupted Z-double bonds show moderate cytotoxic activities against tumor cell lines (Jurkat, K562, U937, HL60, HeLa), human embryonic kidney cells (Hek293), normal fibroblasts and human topoisomerase I (hTop1) inhibitory activity in vitro. The synthesized acids efficiently initiate apoptosis of Jurkat tumor cells, with the cell death mechanism being activated by the mitochondrial pathway. A probable mechanism of topoisomerase I inhibition was also hypothesized on the basis of in silico studies resorting to docking. The activation and inhibition of the most versatile intracellular signaling pathways (CREB, JNK, NFkB, p38, ERK1/2, Akt, p70S6K, STAT3 and STAT5 tyrosine kinases) responsible for cell proliferation and for initiation of apoptosis were studied by multiplex assay technology (Luminex xMAP).

Alkenyl Carbonyl Derivatives in Enantioselective Redox Relay Heck Reactions: Accessing α,β-Unsaturated Systems

A highly enantioselective and site-selective Pd-catalyzed arylation of alkenes linked to carbonyl derivatives to yield α,β-unsaturated systems is reported. The high site selectivity is attributed to both a solvent effect and the polarized nature of the carbonyl group, both of which have been analyzed through multidimensional analysis tools. The reaction can be performed in an iterative fashion allowing for a diastereoselective installation of two aryl groups along an alkyl chain.

Chain-modified pyridino-N substituted nicotine compounds for use in the treatment of CNS pathologies

Compounds for treating abuse of nicotinic receptor agonists, addiction to psychostimulant drugs, addiction to opiates, addiction to alcohol, addiction to tobacco products, addiction to nicotine, schizophrenia and related diseases, depression and related conditions, Alzheimer's disease, Parkinson's disease, irritable bowel syndrome, and colitis. The compounds competitively inhibit central nervous system acting nicotinic receptor agonists and act at the putative α3β2* and α4β2 neuronal nicotinic receptors in the central nervous system.

Studies related to fatty acids desaturation. II. Preparation of iso-linoleic and iso-vernolic acids

New iso-vernolic and iso-linoleic acids have been prepared in order to study their potential inhibition action during in vivo desaturation of oleic acid in vegetal sources. - Keywords: Δ12-desaturase / modified fatty acids / Z,ω-octenyl bromides / iso-linoleic acids / iso-vernolic acids

An efficient and stereoselective synthesis of insect pheromones by way of nickel-catalyzed Grignard reactions. Syntheses of gossyplure and pheromones of Eudia pavonia and Droxophila melanogaster

Three pheromones, (6Z,11Z)-hexadeca-6,11-dien-1-yl acetate (from Eudia pavonia), (5Z,9Z)-heptacosa-5,9-diene (from Drosophila melanogaster) and gossyplure, have been synthesized each by two consecutive consequences of nickel-assisted Grignard reactions with cyclic enol ethers and preparation of Grignard reagents from the resultant alcohols.

SHORT, REGIO- AND STEREO-SELECTIVE PREPARATION OF 1,5- AND 1,6-DIENES. SYNTHESES OF EUDIA PAVONIA PHEROMONE AND GOSSYPLURE.

Two pheromones, (Z)-6,(Z)-11-hexadecadien-1-yl acetate (from Eudia pavonia) and gossyplure, have been synthesized each by two consecutive sequences of nickel-assisted Grignard reactions with cyclic enol ethers and the preparation of Grignard reagents from the resultant alcohols, followed each by copper-promoted Grignard reaction with a small-ring ether and subsequent acetylation.

Selective Cleavage of Dimethylhydrazones to the Carbonyl Compounds Using Silica Gel and its Application in the Synthesis of (Z)-9-Tetradecenyl Acetate

A new method for the selective hydrolytic cleavage of dimethylhydrazones consists of treatment of the hydrazones with silica gel (pH 6.80) in wet tetrahydrofuran.Utilizing this method as one of the key steps, (Z)-9-tetradecenyl acetate, the pheromone of Spodoptera frugiperda, was synthesized.

Syntheses of Monounsaturated Sex Pheromones of Lepidoptera via 3-Alkyn-1-ols

3-Alkyn-1-ols as intermediate synthons in the preparation of some Lepidoteran sex pheromones were utilized.Characteristic fragmentations reflecting the position of the triple bond were found in the mass spectra of 3-alkyn-1-ols and alkyn-1-yl acetates in contrast to 1-tert-butoxy-alkynes.A partial isomerization of 1-tosyloxy-3-(Z)-octene to 1-bromo-3-(E)-octene within the reaction with NaBr in DMF was noticed by GC and 13C-n.m.r., for which a mechanism involving homoconjugation in an intermediate non-classical carbonium ion was suggested.