928-89-2

Basic information

• Product Name: 6-Chlorohex-1-ene
• Synonyms: 6-chloro-1-hexen;6-CHLORO-1-HEXENE;6-chlorohex-1-ene;5-Hexenyl chloride;6-Chloro-1-hexene,97%;Chloro-1-hex
• CAS NO: 928-89-2
• Molecular Formula: C₆H₁₁Cl
• Molecular Weight: 118.6
• EINECS: 213-186-5
• Product Categories: Alkenyl;Halogenated Hydrocarbons;Organic Building Blocks
• Mol File: 928-89-2.mol
• Article Data: 24

Chemical Properties

• Boiling Point: 135-136 °C(lit.)
• Flash Point: 84 °F
• Appearance: Clear colorless to light yellow/Liquid
• Density: 0.896 g/mL at 25 °C(lit.)
• Vapor Pressure: 7.64mmHg at 25°C
• Refractive Index: n20/D 1.438(lit.)
• Storage Temp.: Flammables area
• Stability: Stable. Flammable. Incompatible with strong oxidizing agents.
• CAS DataBase Reference: 6-Chlorohex-1-ene(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Chlorohex-1-ene(928-89-2)
• EPA Substance Registry System: 6-Chlorohex-1-ene(928-89-2)

Safety Data

• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 16-26-36-37/39
• RIDADR: UN 3295 3/PG 2
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 3
• Hazardous Substances Data: 928-89-2(Hazardous Substances Data)

Usage

Chemical Properties

colourless liquid

Uses

6-Chloro-1-hexene is used as pharmaceutical intermediate.

General Description

6-Chloro-1-hexene is an ω-chloro-1-alkene. It reacts with β-substituted imines in the presence of a rhodium catalyst to afford tri- and tetra-substituted imines. It undergoes cross-coupling reaction in the presence of copper(II) chloride and 1-phenylpropyne.

InChI:InChI=1/C6H11Cl/c1-2-3-4-5-6-7/h2H,1,3-6H2

Upstream product

• 56-23-5 tetrachloromethane 
• 112142-22-0 tri(1-hexene-6-yl)phosphite 
• 71042-21-2 4-methylbenzenesulfonic acid 6-chlorohexyl ester 
• 63668-13-3 Δ⁵-hexenylmercury chloride 
• 6294-17-3 1-bromo-6-chlorohexane 
• 2206-26-0 [D₃]acetonitrile 
• 34683-73-3 1-chloro-6-iodohexane 
• 4303-49-5 diethyl [²H₂]malonate 
• 16183-00-9 5-hexen-1-yl radical 
• 111860-31-2 5-hexenyl<1-hydroxy-1-methylethyl>diazene 
• 1577-22-6 5-hexenoic acid 
• 109-70-6 1.3-chlorobromopropane 
• 106-95-6 allyl bromide 
• 10297-06-0 1-chloro-5-hexyne 

Downstream Products

• 10226-30-9 6-chloro-2-hexanone 
• 213971-97-2 1-(hex-5-enyl)cyclohexanol 
• 1123881-19-5 (6-chloro-n-hex-1-yl)diphenylphosphine oxide 
• 1119-60-4 hept-6-enoic acid 
• 81097-32-7 N-hex-5-enyl(4-methylphenyl)sulfonamide 
• 1431847-32-3 4-(4-chlorobutyl)-2-(phenylsulfonyl)-3,4-dihydro-2H-benzo[e][1,2]thiazine-1,1-dioxide 
• 1407797-85-6 (R)-(9-chloro-1-nonen-3-yl)dimethylphenylsilane 

Relevant articles and documents

Synthesis of 11-methyl-13-azabicyclo[7.3.1]trideca-3,10-diene, a macrobicycle with the 9b-azaphenalene carbon framework, based on the combination of allylboration and intramolecular metathesis

A four-step synthesis of 11-methyl-13-azabicyclo[7.3.1]trideca-3,10-diene, a potential precursor of the ladybugs defensive alkaloids precoccinelline and mirrhine, has been accom-plished. Treatment of 4-picoline with 5-hexenyl-1-lithium, triallylborane, and methanol led to the synthesis of trans-6-allyl-2-(hex-5-enyl)-4-methyl-1,2,3,6-tetrahydropyridine, which reacted with triallylborane upon heating to be converted to the cis-isomer. A subsequent cyclization of the cis-isomer of N-Boc derivative via the intramolecular metathesis using Grubbs II and Hoveyda - Grubbs II ruthenium catalysts furnished the target bridged macrobicycle. The structure of its hydrochloride was confirmed by single crystal X-ray diffraction studies. The optimal conditions for the metathesis reaction and the isolation of the macrobicyclic product were selected.

Controlling the Lewis Acidity and Polymerizing Effectively Prevent Frustrated Lewis Pairs from Deactivation in the Hydrogenation of Terminal Alkynes

Two strategies were reported to prevent the deactivation of Frustrated Lewis pairs (FLPs) in the hydrogenation of terminal alkynes: reducing the Lewis acidity and polymerizing the Lewis acid. A polymeric Lewis acid (P-BPh3) with high stability was designed and synthesized. Excellent conversion (up to 99%) and selectivity can be achieved in the hydrogenation of terminal alkynes catalyzed by P-BPh3. This catalytic system works quite well for different substrates. In addition, the P-BPh3 can be easily recycled.

Unexpectedly selective hydrogenation of phenylacetylene to styrene on titania supported platinum photocatalyst under 385 nm monochromatic light irradiation

Conversion of alkynes to alkenes by photocatalysis has inspired extensive interest, but it is still challenging to obtain both high conversion and selectivity. Here we first demonstrate the photocatalytic conversion of phenylacetylene (PLE) to styrene (STE) with both high conversion and selectivity by using the titania (TiO2) supported platinum (Pt) as photocatalyst under 385 nm monochromatic light irradiation. It is demonstrated that the conversion rate of PLE is strongly dependent on the content of Pt cocatalyst loaded on the surface of TiO2. Based on our optimization, the conversion of PLE and the selectivity towards STE on the 1 wt% Pt/TiO2 photocatalyst can unexpectedly reach as high as 92.4% and 91.3%, respectively. The highly selective photocatalytic hydrogenation can well be extended to the conversion of other typical alkynes to alkenes, demonstrating the generality of selective hydrogenation of C≡C over the Pt/TiO2 photocatalyst.