4549-32-0

Basic information

• Product Name: 1,8-Dibromooctane
• Synonyms: 1,8-Dibromooctane,98%;Octane, 1,8-dibromo-;1,8-DIBROMOOCANE;1,8-Dibromooctane,Octamethylene dibromide;1,8-DibroMooctane, 98% 10ML;Octamethylene Bromide Octamethylene Dibromide;1,8-DibroMooCLane;1,8-DIBROMOOCTANE FOR SYNTHESIS
• CAS NO: 4549-32-0
• Molecular Formula: C₈H₁₆Br₂
• Molecular Weight: 272.02
• EINECS: 224-912-5
• Product Categories: Bromine Compounds;alpha,omega-Bifunctional Alkanes;alpha,omega-Dibromoalkanes;Monofunctional & alpha,omega-Bifunctional Alkanes;Pyridines ,Halogenated Heterocycles
• Mol File: 4549-32-0.mol

Chemical Properties

• Melting Point: 12-16 °C(lit.)
• Boiling Point: 270-272 °C(lit.)
• Flash Point: >230 °F
• Appearance: Clear yellow/Liquid
• Density: 1.477 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.011mmHg at 25°C
• Refractive Index: n20/D 1.498(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: Chloroform (Sparingly), Hexanes (Slightly)
• Water Solubility: Insoluble
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents, strong bases.
• BRN: 1698114
• CAS DataBase Reference: 1,8-Dibromooctane(CAS DataBase Reference)
• NIST Chemistry Reference: 1,8-Dibromooctane(4549-32-0)
• EPA Substance Registry System: 1,8-Dibromooctane(4549-32-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 4549-32-0(Hazardous Substances Data)

Usage

Uses

Furthermore, 1,8-dibromooctane is used in the preparation of (1,4-bis-(8-bromooctyloxy)-benzene), a compound that finds applications in various industries, such as the production of polymers, pharmaceuticals, and agrochemicals. The presence of bromine atoms in the 1,8-dibromooctane molecule allows for the formation of new chemical bonds and reactions, making it a valuable intermediate in the synthesis of various organic compounds.

Synthesis Reference(s)

The Journal of Organic Chemistry, 30, p. 780, 1965 DOI: 10.1021/jo01014a031

Synthesis

1,8-Dibromooctane was prepared by the reaction of cyclooctene with sulfuric acid and hydrobromination under the catalyst.

InChI:InChI=1/C8H16Br2/c9-7-5-3-1-2-4-6-8-10/h1-8H2

Upstream product

• 629-41-4 1,8-Octanediol 
• 51306-09-3 1,8-dimethoxyoctane 
• 32038-98-5 N,N'-Octamethylenedibenzamide 
• 110042-34-7 1,8-bis(p-anisyloxy)octane 
• 111-20-6 1,10-decanedioic acid 
• 116728-38-2 octanedioic acid; disilver salt 
• 3710-30-3 1,7-Octadiene 
• 110-52-1 1,4-dibromo-butane 
• 56-23-5 tetrachloromethane 
• 7726-95-6 bromine 
• 10035-10-6 hydrogen bromide 
• 94377-57-8 1,8-bis-pentyloxy-octane 
• 7789-69-7 phosphorus pentabromide 
• 629-03-8 1 ,6-dibromohexane 

Downstream Products

• 296-30-0 1,10-Diaza-cyclooctadecan 
• 120808-65-3 1,10-bis(p-tolylsulphonyl)-1,10-diazacyclo-octadecane 
• 94680-04-3 1,8-bis(4-nitrophenoxy)octane 
• 110662-67-4 1,8-bis-(2-nitro-phenoxy)-octane 
• 51306-09-3 1,8-dimethoxyoctane 
• 61575-01-7 1,8-diphenoxyoctane 
• 17702-83-9 N-8-bromooctylphthalimide 
• 1191-62-4 octane-1,8-dithiol 
• 593-12-4 1-bromo-8-fluorooctane 
• 83492-49-3 N¹,N⁸-di(p-toluenesulfonyl)-1,8-diaminooctane 
• 102702-38-5 1,4-bis((8’-bromooctyl)oxy)benzene 
• 58593-33-2 1,8-bis(2-hydroxyethylthio)octane 
• 119621-53-3 4,4'-bis-ethoxycarbonyl-1,1'-dimethyl-4,4'-diphenyl-dodecahydro-1,1'-octanediyl-bis-azepinium; dibromide 

Relevant articles and documents

Process intensification-assisted conversion of α,ω-alkanediols to dibromides

The increasingly widespread applications of α,ω-dibromides motivated development of a scalable, inexpensive process to rapidly convert selected α,ω-alkanediols to the corresponding dibromides. Diols were heated with only 48% aq HBr and an organic solvent, using a Dean-Stark apparatus modified to fractionate the azeotropic distillate, thereby maintaining a higher HBr concentration and reaction rate in the pot. Intensified distillation also increased the reaction rate. Various other substrate, solvent, and parameter effects have been discovered and rationalized.

First syntheses of model long-chain trichloro[ω-(trimethylsilyl)alkynyl]silanes suitable for self-assembled monolayers on silicon surfaces

The preparation of the title compounds involves the introduction of the required Me3SiC{triple bond, long}C and trichlorosilyl groups at the termini of the alkyl chain via derivatization of easily accessible and inexpensive materials/reagents. Trichloro[ω-(trimethylsilyl)alkynyl]silanes are useful for the linkage to a hydroxylated silicon surface for multilayer formation and for further chemical modification of the tail group of the monolayer.

ALLYL SULFIDE COMPOUNDS, AND COMPOSITIONS AND METHODS USING SAID COMPOUNDS FOR REPELLING BLOOD-FEEDING ARTHROPODS

This invention relates to compositions of one or more compounds that incorporate one or more allyl sulfide, allyl disulfide or allyl polysulfide moieties, or one or more allyl sulfide, allyl disulfide or allyl polysulfide moieties and one or more hydroxyl groups, used in effective amount in formulations, including emulsions, to repel blood-feeding ectoparasitic arthropods, including mosquitoes, and to deter them from landing and feeding when applied to the skin, clothing or environment of animals, including humans. Said compounds can include, but are not limited to, 8-allyl-sulfanyloctan-1-ol. This invention also relates to compositions comprising one or more of said compounds in further combination with other arthropod repellent and deterrent compounds, including vanillin. These compounds may be formulated with inert ingredients to form a liquid, gel, paste, soap, spray, aerosol or powder.

Ionic liquids as reagents and solvents in conjunction with microwave heating: Rapid synthesis of alkyl halides from alcohols and nitriles from aryl halides

We show that using ionic liquids as reagents in conjunction with microwave heating it is possible to prepare primary alkyl halides from the corresponding alcohols rapidly. Using ionic liquids as solvents in conjunction with microwave heating it is possible to prepare aryl nitriles from the corresponding aryl bromides or iodides. The scope and limitations of using microwave-promotion as a tool in these reactions is discussed.

First Synthesis of the Cytotoxic and Antifungal C14-Amine (2S,3E,5Z)-2-Amino-3,5,13-tetradecatriene Isolated from the New Zealand Ascidian Pseudodistoma novaezelandiae

The synthesis of (2S,3E,5Z)-2-amino-3,5,13-tetradecatriene with high enantiomeric purity in excellent overall yield is described.In the crucial step the stereogenic center was generated by nucleophilic addition of tert-butyl carbamate to a planar-chiral tetracarbonyliron(1+) complex. Key Words: (2S,3R,5Z)-2-Amino-3,5,13-tetradecatriene / Cytotoxic agents / Antifungal agents / Amination / Iron-mediated allylic amination / Pseudodistoma novaezelandiae

Enantioselective Total Synthesis of Harmonine, a Defence Alkaloid of Ladybugs (Coleoptera: Coccinellidae)

An efficient and highly enantioselective (ee > 97percent) total synthesis of the ladybug defence alkaloid (17R,9Z)-1,17-diaminooctadec-9-ene in good overall yield is described.As the key step for the generation of the stereogenic center, asymmetric C-C bond formation by nucleophilic addition of methyllithium to an aldehyde SAMP hydrazone is used. Key Words: (17R,9Z)-1,17-Diaminooctadec-9-ene / Harmonine / Ladybug / SAMP hydrazone

Directed Synthesis of Translationally Isomeric -Catenanes

In a multi-step reaction sequence the tetrahydroxymetacyclophane 12c is synthesized.Acetalisation with 1,25-dichloro-13-pentacosanone followed by nitration and reduction afforded the diamine 13c.By cyclization of this compound in 2-pentanol with sodium carbonate and sodium iodide under high dilution conditions the monomeric products 16, 17, and 18 are obtained in yields of 21.4, 7.7, and 0,9percent, respectively.On the basis of mass, 13C NMR and 1H NMR spectra the structure of these compounds is discussed.Starting from the precatenane 16 the -catenanes 25a,b,c and 26a,b,c are obtained in a multi-step reaction sequence.The structure of these compounds is confirmed by mass, 13C NMR, and 1H NMR spectroscopic investigations.

Process for preparing olefinic aldehydes

A process for the preparation of olefinic aldehydes and intermediates is disclosed. The condensation of an α,ω-dihalide with a metal acetylide gives an acetylenic halide which can be reduced to give an olefinic halide, then oxidized to give the desired olefinic aldehyde or the acetylenic halide can be oxidized first to give an acetylenic aldehyde and then reduced to give the desired olefinic aldehyde.