19763-13-4

Basic information

• Product Name: 1,6-HEXANEDIOL DIVINYL ETHER
• Synonyms: 1,6-HEXANEDIOL DIVINYL ETHER;1,6-bis(vinyloxy)hexane;Hexanediol divinyl ether;1 6-HEXANEDIOL DIVINYL ETHER 97%;Hexanediol 1,6-divinyl ether;1,6-Bis(ethenyloxy)hexane;1,6-Di(vinyloxy)hexane;1,6-Hexanediylbis(vinyl ether)
• CAS NO: 19763-13-4
• Molecular Formula: C₁₀H₁₈O₂
• Molecular Weight: 170.25
• EINECS: 243-277-5
• Mol File: 19763-13-4.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 205 °C(lit.)
• Flash Point: 199 °F
• Appearance: /
• Density: 0.887 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0843mmHg at 25°C
• Refractive Index: n20/D 1.446(lit.)
• CAS DataBase Reference: 1,6-HEXANEDIOL DIVINYL ETHER(CAS DataBase Reference)
• NIST Chemistry Reference: 1,6-HEXANEDIOL DIVINYL ETHER(19763-13-4)
• EPA Substance Registry System: 1,6-HEXANEDIOL DIVINYL ETHER(19763-13-4)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 19763-13-4(Hazardous Substances Data)

Usage

Description

1,6-Hexanediol divinyl ether, with the chemical formula C10H18O2, is a colorless, flammable liquid characterized by a sweet odor. It is a reactive compound used extensively in the chemical industry for various applications due to its versatile properties.

Uses

Used in Polymer Industry:
1,6-Hexanediol divinyl ether is used as a crosslinking agent in polymerization processes for enhancing the mechanical properties and stability of the resulting polymers. Its ability to form covalent bonds with other monomers contributes to the creation of three-dimensional networks within polymers, improving their overall performance.
Used in Specialty Polymers and Copolymers Preparation:
As a monomer, 1,6-hexanediol divinyl ether is utilized in the synthesis of specialty polymers and copolymers that possess unique properties tailored for specific applications. Its reactivity allows for the development of materials with tailored characteristics, such as improved thermal stability, chemical resistance, and mechanical strength.
Used in Solvent Applications:
1,6-Hexanediol divinyl ether serves as a solvent in various chemical processes due to its ability to dissolve a wide range of substances. Its solubility properties make it suitable for use in formulations that require the dissolution of specific compounds for further reactions or applications.
Used as an Intermediate in Organic Synthesis:
In the synthesis of other organic compounds, 1,6-hexanediol divinyl ether acts as an intermediate. Its reactive nature allows it to participate in multiple chemical reactions, contributing to the formation of a variety of end products in the organic chemistry field.
Safety Precautions:
Given its reactive nature, 1,6-hexanediol divinyl ether should be handled with care to prevent skin and eye irritation. It is also harmful if swallowed or inhaled, necessitating proper safety measures during its use, storage, and disposal.

InChI:InChI=1/C10H18O2/c1-3-11-9-7-5-6-8-10-12-4-2/h3-4H,1-2,5-10H2

Upstream product

• 629-11-8 1,6-hexanediol 
• 108-05-4 vinyl acetate 
• 111-34-2 -butyl vinyl ether 
• 109-92-2 ethyl vinyl ether 
• 74-86-2 acetylene 

Downstream Products

• 1411984-91-2 2-(6-[2-(diphenethylphosphoroselenoyl)ethoxy]hexyloxy)ethyl(diphenethyl)phosphine selenide 
• 1411984-82-1 2-(6-[2-(diphenethylphosphorothioyl)ethoxy]hexyloxy)ethyl(diphenethyl)phosphine sulfide 
• 1355021-74-7 1,6-bis(1-(2-formylaminophenoxy)ethoxy)hexane 

Relevant articles and documents

Reductive C-O, C-N, and C-S Cleavage by a Zirconium Catalyzed Hydrometalation/β-Elimination Approach

A zirconium catalyzed reductive cleavage of Csp3 and Csp2 carbon-heteroatom bonds is reported that makes use of a tethered alkene functionality as a traceless directing group. The reaction is successfully demonstrated on C-O, C-N, and C-S bonds and proposed to proceed via a hydrozirconation/β-heteroatom elimination sequence of an in situ formed zirconium hydride catalyst. The positional isomerization of the catalyst further enables the cleavage of homoallylic ethers and the removal of terminal allyl and propargyl groups.

Au(I) complexes-catalyzed transfer vinylation of alcohols and carboxylic acids

Au(I) complexes-catalyzed transfer vinylation of alcohols and carboxylic acids has been achieved. The catalyst system consists of 2 mol % AuClPPh3 and 2 mol % AgOAc. Primary alcohols and secondary alcohols were converted into corresponding vinyl ethers in good yield (64-93%); however, tertiary alcohols showed poor reactivities. Carboxylic acids were also transformed into corresponding vinyl esters in good yield (78-96%).

Synthesis of allyl and alkyl vinyl ethers using an in situ prepared air-stable palladium catalyst. Efficient transfer vinylation of primary, secondary, and tertiary alcohols

An air-stable palladium catalyst formed in situ from commercially available components efficiently catalyzed the transfer vinylation between butyl vinyl ether and various allyl and alkyl alcohols to give the corresponding allyl and alkyl vinyl ethers in 61-98% yield in a single step.