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

Chemical Properties

colourless liquid

Uses

6-Bromo-1-hexene was used in the preparation of epoxide, 6-bromo-1,2-epoxyhexane. It was also used in a simple, direct preparation of 4-alkenylbenzonitriles via anionic reduced forms of terephthalonitrile in liquid ammonia.

Synthesis Reference(s)

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

General Description

Reaction of 6-bromo-1-hexene with Mg to form Grignard compounds has been investigated. The thermal chemistry of 6-bromo-1-hexene on Ni (100) surface has been studied under ultrahigh vacuum conditions by X-ray photoelectron spectroscopy and temperature-programmed desorption.

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

Upstream product

• 821-41-0 5-Hexen-1-ol 
• 592-42-7 1,5-Hexadien 
• 110-52-1 1,4-dibromo-butane 
• 917-57-7 vinyllithium 
• 64818-36-6 5-hexenyl methanesulfonate 
• 10035-10-6 hydrogen bromide 
• 629-03-8 1 ,6-dibromohexane 
• 1608-26-0 Hexamethylphosphorous triamide 
• 34626-51-2 5-bromopentan-1-ol 
• 1191-30-6 5-bromopentanal 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 111-29-5 1 ,5-pentanediol 
• 1110667-68-9 O-hex-5-enyl dimethylcarbamothioate 
• 18420-41-2 2-(chloromethyl)tetrahydropyran 

Downstream Products

• 88563-41-1 2-Hex-5-enyl-2-phenyl-[1,3]dithiane 
• 55563-69-4 α-hex-5-enylbenzyl alcohol 
• 59137-64-3 α-(cyclopentylmethyl)benzyl alcohol 
• 133709-72-5 cis 1,3-Dibenzyl-4-(hex-5'-enyl)-4-hydroxy-2,3,3a,4,6,6a-hexahydrofuro<3,4-d>imidazol-2-one 
• 133709-73-6 trans 1,3-Dibenzyl-4-(hept-6'-enoyl)-5-hydroxymethylimidazolidine-2-one 
• 4165-80-4 1,1-diphenyl-5-hepten-1-ol 
• 59137-57-4 2-cyclopentyl-1,1-diphenylethanol 
• 91766-89-1 4-(5-hexenyl)-1-chlorobenzene 
• 592-41-6 1-hexene 
• 96-37-7 methyl-cyclopentane 
• 110-82-7 cyclohexane 
• 139461-44-2 C₉H₂₂S₃Si 
• 139461-45-3 C₁₅H₃₄S₃Si 
• 134784-86-4 (3R,4S,5S)-3,4,5-tribenzyloxydodeca-1,11-dien-6-ol 

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.

Aromatic Claisen Rearrangements of Benzyl Ketene Acetals: Conversion of Benzylic Alcohols to (ortho-Tolyl)acetates

Claisen rearrangements of benzyl vinyl ethers are much less facile than those of aliphatic allyl vinyl ethers, and their synthetic utility has remained relatively unexplored. A one-pot procedure is reported for the generation and Claisen rearrangement of benzyl vinyl ethers that contain an activating α-alkoxy substituent on the vinyl group. A [3,3]-sigmatropic mechanism was supported by trapping of the intermediate isotoluene in an intramolecular Alder–ene reaction.