2695-47-8

Basic information

• Product Name: 6-Bromo-1-hexene
• Synonyms: BROMO(6-)-1-HEXENE;5-HEXEN-1-YL BROMIDE;6-BROMO-1-HEXENE;6-BROMOHEX-1-ENE;1-Bromo-5-hexene;1-Bromohex-5-ene;1-Hexene,6-bromo-;5-Hexenyl bromide
• CAS NO: 2695-47-8
• Molecular Formula: C₆H₁₁Br
• Molecular Weight: 163.06
• EINECS: 220-267-9
• Product Categories: Aliphatics;Halides;omega-Functional Alkanols, Carboxylic Acids, Amines & Halides;omega-Unsaturated Halides;Alkenyl;Halogenated Hydrocarbons;Organic Building Blocks;Intermediates
• Mol File: 2695-47-8.mol
• Article Data: 34

Chemical Properties

• Melting Point: -102.35°C (estimate)
• Boiling Point: 47-51 °C16 mm Hg(lit.)
• Flash Point: 126 °F
• Appearance: Clear slightly yellow/Liquid
• Density: 1.22 g/mL at 25 °C(lit.)
• Vapor Pressure: 4.36mmHg at 25°C
• Refractive Index: n20/D 1.4652(lit.)
• Storage Temp.: Refrigerator
• Water Solubility: Not miscible in water.
• Stability: Stable. Incompatible with strong oxidizing agents, strong bases. Flammable.
• BRN: 506203
• CAS DataBase Reference: 6-Bromo-1-hexene(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Bromo-1-hexene(2695-47-8)
• EPA Substance Registry System: 6-Bromo-1-hexene(2695-47-8)

Safety Data

• Hazard Codes: Xi,F,T
• Statements: 10-36/37/38-61
• Safety Statements: 26-36-37/39-16-45-53
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• F: 8
• TSCA: T
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 2695-47-8(Hazardous Substances Data)

Usage

Description

6-Bromo-1-hexene is a colorless liquid that is known for its unique chemical properties. It is an organic compound with the molecular formula C6H11Br, which consists of a hexene chain with a bromine atom attached to the sixth carbon. 6-Bromo-1-hexene has been widely studied for its various applications in the chemical industry, particularly in the synthesis of other compounds.

Uses

Used in Chemical Synthesis:
6-Bromo-1-hexene is used as a key intermediate in the chemical synthesis of various compounds. Its ability to form Grignard compounds upon reaction with magnesium has been extensively investigated, making it a valuable starting material for the preparation of a range of organic molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 6-Bromo-1-hexene is used as a precursor for the preparation of epoxides, such as 6-bromo-1,2-epoxyhexane. These epoxides are important intermediates in the synthesis of various pharmaceutical compounds, including those with potential therapeutic applications.
Used in Material Science:
6-Bromo-1-hexene is also utilized in the preparation of 4-alkenylbenzonitriles, which are important building blocks for the synthesis of polymers and other materials with specific properties. The simple and direct preparation of these compounds using anionic reduced forms of terephthalonitrile in liquid ammonia has been demonstrated, highlighting the versatility of 6-Bromo-1-hexene in material science applications.
Used in Surface Chemistry Studies:
The thermal chemistry of 6-bromo-1-hexene on Ni (100) surface has been studied under ultrahigh vacuum conditions using X-ray photoelectron spectroscopy and temperature-programmed desorption. These studies contribute to the understanding of the interaction between 6-Bromo-1-hexene and metal surfaces, which is crucial for various applications in catalysis and surface modification.

Synthesis Reference(s)

Synthesis, p. 885, 1984 DOI: 10.1055/s-1984-31010

InChI:InChI=1/C6H11Br/c1-2-3-4-5-6-7/h2H,1,3-6H2

Upstream product

• 629-11-8 1,6-hexanediol 
• 110-52-1 1,4-dibromo-butane 
• 917-57-7 vinyllithium 
• 592-42-7 1,5-Hexadien 
• 821-41-0 5-Hexen-1-ol 
• 111-29-5 1 ,5-pentanediol 
• 1191-30-6 5-bromopentanal 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 34626-51-2 5-bromopentan-1-ol 
• 629-03-8 1 ,6-dibromohexane 
• 1608-26-0 Hexamethylphosphorous triamide 
• 18420-41-2 2-(chloromethyl)tetrahydropyran 
• 2009-83-8 6-chloro-1-hexanol 
• 77022-44-7 6-(tetrahydropyran-2-yloxy)hex-1-ene 

Downstream Products

• 88563-41-1 2-Hex-5-enyl-2-phenyl-[1,3]dithiane 
• 87013-17-0 o-Hydroxyphenyl 5-hexenyl ether 
• 155800-61-6 2-<4-<4-(hex-5-enyloxy)phenylazo>phenyl>ethyl alcohol 
• 393860-85-0 1-(4-hexenyl)-2(1H)-pyrazinone 
• 859857-38-8 18,23-butane-19,22-diylbis(14-{[(2R,3R,4S,5R,6S)-4,5-bis(benzyloxy)-3-(hex-11-ene-7-yloxy)-6-methoxytetrahydro-2H-pyran-2-yl]methyl}-1H-14,15,16-triazole) 
• 886755-24-4 (E)-3-Oxo-12-phenyl-dodec-9-enoic acid ((S)-2-oxo-tetrahydro-furan-3-yl)-amide 
• 886755-21-1 3-Oxo-dec-9-enoic acid ((S)-2-oxo-tetrahydro-furan-3-yl)-amide 
• 908127-14-0 tris-(4-hex-5-enyloxy-phenyl)-phosphane 
• 865288-75-1 2,5-bis(5-hexenyloxy)p-xylylene alcohol 
• 865288-76-2 2,5-bis(5-hexenyloxy)benzene-1,4-dicarbaldehyde 
• 862603-33-6 (5S)-3-[(R)-2-(tert-butyldimethylsilyloxy)non-8-enyl]-5-methyl-3-phenylthio-3H-dihydrofuran-2-one 
• 932-66-1 1-cyclohexenyl methyl ketone 
• 115595-28-3 4-(hex-5-en-1-yloxy)benzoic acid 

Relevant articles and documents

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A useful modification of the Kraus procedure1 for preparation of ω-bromo-1-alkenes by HMPA-promoted elimination of HBR from 1,ω-dibromoalkanes

A reliable, reproducible, general, and detailed procedure for the mono-elimination of hydrogen bromide from 1,ω-dibromoalkanes is described.

Mechanistic Insights into FLP-Catalyzed Iodoperfluoroalkylations

The frustrated Lewis pair-catalyzed iodoperfluoroalkylation of olefins, its substrate activation mode, and catalyst degradation pathways are mechanistically investigated by kinetic measurements. The transformation most likely proceeds via coordination of the phosphane to the perfluoroalkyl iodide and involves radical intermediates.

Simple and high yield access to octafunctional azido, amine and urea group bearing cubic spherosilicates

Spherosilicates and polyhedral oligomeric silsesquioxanes represent unique well-defined rigid building blocks for molecular and hybrid materials. Drawbacks in their synthesis are often low yields and the restricted presence of functional groups either based on incomplete transformation of all corners or the reactivity of the functional groups. Particularly amine-functionalization reveals some synthetic challenges. In this study we report the synthesis of a new class of octafunctionalized hydrogen bond forming spherosilicates via a facile route based on octabromo alkyl functionalized cubic spherosilicates. Four different alkyl chain lengths, namely C4, C5, C6 and C11, were realized starting from ω-alkenylbromides via hydrosilylation of Q8M8H. Using sodium azide in a mixture of acetonitrile:DMF = 10:1, the octaazide was obtained quantitatively and could be rapidly transformed in an octaamine cube via catalytic hydrogenation over Pd/C in absolute ethanol. The following reaction to hydrogen bond forming spherosilicates was performed in situ by adding propyl isocyanate. All transformations proceed quantitatively at the eight corners of the cube, which was evidenced by NMR spectroscopy and ESI-MS measurements. The Q8-target compound can be separated after each reaction step over simple chemical workup while no cage rearrangement was observed. The structures were confirmed using 1H, 13C, 29Si-NMR, FT-IR, elemental analysis and ESI-MS. The method opens a high yield route (overall isolated yield 83-88%) for structural building blocks in hybrid materials.