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5-Vinylnorborn-2-ene is a bicyclic unsaturated hydrocarbon containing a norbornene framework with an additional vinyl substituent, giving the molecule two carbon–carbon double bonds and a highly constrained three-dimensional structure.
5-Vinylnorborn-2-ene is also known as 5-vinyl-2-norbornene, 5-vinylnorbornene, and 5-vinylbicyclo[2.2.1]hept-2-ene, names that describe the same substituted norbornene structure.
5-Vinylnorborn-2-enes combination of a strained bicyclic skeleton, an endocyclic double bond, and an exocyclic vinyl group makes it a reactive monomer and useful starting material for polymer and specialty-organic synthesis.
CAS Number: 3048-64-4
Molecular Formula: C9H12
Molecular Weight: 120.19
EINECS Number: 221-259-8
Synonyms: 5-Vinyl-2-norbornene, 3048-64-4, 2-Vinylnorbornene, VINYLNORBORNENE, 5-Vinylnorbornene, 2-Vinyl-5-norbornene, 2-Norbornene, 5-vinyl-, 5-Vinylnorborn-2-ene, 5-Vinylbicyclo[2.2.1]hept-2-ene, DTXSID6029250, 2-Vinylbicyclo(2.2.1)hept-5-ene, 5-Vinylbicyclo(2.2.1)hept-2-ene, O26JW4DH9I, DTXCID809250, 2-Vinylbicyclo[2.2.1]hept-5-ene, NSC-61529, RefChem:913586, 5,2-VNB, 221-259-8, 5-ethenylbicyclo[2.2.1]hept-2-ene, Bicyclo[2.2.1]hept-2-ene, 5-ethenyl-, 117110-17-5, NSC 61529, 117110-18-6, MFCD00080691, Vinylnorbornene (VAN), endo-5-Vinylbicyclo(2,2,1)hept-2-ene, Bicyclo(2.2.1)hept-2-ene, 5-ethenyl-, 25093-48-5, HSDB 6336, EINECS 221-259-8, BRN 1903874, CCRIS 8479, 6-ethenylbicyclo[2.2.1]hept-2-ene, exo-5-Vinylbicyclo(2.2.1)hept-2-ene, Exo-5-vinylbicyclo[2.2.1]hept-2-ene, endo-5-Vinylbicyclo(2.2.1)hept-2-ene, Endo-5-vinylbicyclo[2.2.1]hept-2-ene, EC 221-259-8, 5-Vinylnorborn-2-ene, exo-, 7MB375Q99R, Bicyclo(2.2.1)hept-2-ene, 5-ethenyl-, (1R,4S,5S)-rel-, 23890-32-6, UNII-ZAF2U4V8LC, UNII-O26JW4DH9I, 5-Vinylbicyclo[2.2.1]hept-2-ene (stabilized with BHT), SCHEMBL43544, UNII-7MB375Q99R, SCHEMBL8513512, SCHEMBL8513515, CHEMBL3186510, Bicyclo(2.2.1)hept-2-ene, 5-ethenyl-. (1R,4S,5R)-rel-, WLN: L55 A CUTJ F1U1, NSC61529, Tox21_201144, 5-Vinylbicyclo[2.2.1]-2-heptene, 2-vinyl-bicyclo[2.2.1]hept-5-ene, 5-ethenylbicyclo[2.2.1]-2-heptene, AKOS025295103, 5-vinylbicyclo[2. 2. 1]hept-2-ene, NCGC00248936-01, NCGC00258696-01, FV170636, SY010942, CAS-3048-64-4, 5-Vinyl-2-norbornene (stabilized with BHT), NS00006439, V0062, EN300-2000456, 5-Vinylbicyclo[2.2.1]hept-2-ene - stabilized with BHT, 5-vinyl-2-norbornen;5-vinyl-2-norbornene[qr];5-Vinylbicyclo[2.2.1]-2-heptene;5-vinylnorbernene;5-Vinylnorbornene;5-vinylnorbornene[qr];bicyclo(2.2.1)hept-2-ene,5-ethenyl-;bicyclo(2.2.1)hept-2-ene,5-ethenyl-[qr]
5-Vinylnorborn-2-ene molecular formula of is C₉H₁₂, with a molecular weight of approximately 120.19 g/mol.
5-Vinylnorborn-2-enes structure contains the bicyclo[2.2.1]hept-2-ene ring system characteristic of norbornene derivatives together with a vinyl group attached at the 5-position.
This architecture provides two chemically distinct unsaturated sites that can exhibit different reactivity depending on the catalyst and reaction conditions. (pubchem.ncbi.nlm.nih.gov)
5-Vinylnorborn-2-ene double bond is part of a strained bicyclic ring, which contributes to the relatively high reactivity of the molecule in addition and polymerization reactions.
The second double bond belongs to the pendant vinyl group and is less constrained than the endocyclic alkene.
The presence of these two alkene functionalities allows selective functionalization or polymerization strategies to be developed depending on the intended application.
5-Vinylnorborn-2-ene is generally described as a colorless to pale yellow liquid with a characteristic hydrocarbon odor.
Its physical state under ordinary conditions is consistent with its relatively low molecular mass and hydrocarbon composition.
Commercial material is commonly supplied with controlled purity because small amounts of related hydrocarbons or polymerization products can affect downstream catalytic or polymerization processes. (tcichemicals.com)
5-Vinylnorborn-2-ene has a boiling point around 140 °C, although the exact reported value can vary depending on the source, purity, and measurement conditions.
Its relatively moderate boiling temperature allows it to be handled as a liquid during many laboratory and industrial operations while still requiring appropriate vapor and ignition control.
Physical-property data should be checked against the specification of the particular commercial grade when designing a process or selecting storage equipment.
The bicyclic structure of 5-Vinylnorborn-2-ene is derived from the norbornene family of strained-ring compounds, which are widely used in polymer chemistry and organic synthesis.
The rigid geometry of the norbornene framework can influence polymer-chain structure and molecular architecture when the compound is incorporated into polymeric materials.
The additional vinyl group provides a second functional site that can be exploited for subsequent chemical modification after or alongside reaction at the norbornene double bond.
The two alkene groups can display different reaction behavior, which is one of the most useful chemical features of 5-Vinylnorborn-2-ene.
The strained norbornene alkene is particularly susceptible to ring-opening metathesis and related transition-metal-catalyzed reactions, whereas the pendant vinyl group can remain available for additional transformations under suitably selective conditions.
This differential reactivity provides opportunities for sequential or orthogonal functionalization in polymer and synthetic chemistry. (pubs.acs.org)
5-Vinylnorborn-2-ene can undergo addition and polymerization reactions because of its two carbon–carbon double bonds.
The norbornene functionality is especially useful in ring-opening metathesis polymerization, where the ring strain provides a thermodynamic driving force for polymer formation.
Depending on the catalyst system, the vinyl group may be retained as a pendant unsaturation, providing an additional handle for later chemical modification. (pubs.acs.org)
5-Vinylnorborn-2-ene is also important as a functionalized norbornene monomer for the preparation of polymers with pendant vinyl groups.
Such polymers can subsequently undergo reactions involving the remaining alkene, allowing the material's chemical functionality to be increased after the initial polymerization step.
This approach is useful in the design of functional polymers, crosslinked networks, and materials whose properties can be adjusted through post-polymerization modification. (pubs.acs.org)
5-Vinylnorborn-2-ene can also serve as a starting material for selective organic functionalization, because the two alkene sites provide multiple possible reaction pathways.
Hydrogenation, oxidation, hydrofunctionalization, and other alkene transformations can modify either or both unsaturated groups depending on the reaction system.
This makes the compound useful when a rigid bicyclic scaffold with additional reactive functionality is required in synthetic chemistry.
The rigid norbornene structure is particularly valuable in materials chemistry, where molecular shape and controlled functionality can influence polymer properties.
Incorporating a norbornene-derived unit into a polymer can contribute to rigidity and distinctive thermal or mechanical behavior, while the pendant vinyl group provides a site for further chemical modification.
Such structural features make 5-Vinylnorborn-2-ene relevant to the development of functional polymeric materials rather than only conventional hydrocarbon synthesis.
5-Vinylnorborn-2-ene is also used in research involving transition-metal-catalyzed olefin reactions, including metathesis, hydrogenation, and selective functionalization.
5-Vinylnorborn-2-enes two nonequivalent alkene groups make it a useful substrate for studying catalyst selectivity and for developing methods capable of distinguishing between structurally similar carbon–carbon double bonds.
These studies can contribute to broader advances in catalytic organic and polymer chemistry.
From a technical perspective, 5-Vinylnorborn-2-ene is best regarded as a strained, bifunctional alkene and functionalized norbornene monomer.
5-Vinylnorborn-2-enes rigid bicyclic framework, ring strain, two distinct carbon–carbon double bonds, and ability to undergo selective catalytic transformations give it value in polymer research, advanced materials, and synthetic organic chemistry.
For industrial use, the appropriate product specification should be selected according to the intended polymerization or chemical transformation, with purity, inhibitor content, and storage requirements considered alongside the desired reactivity. (tcichemicals.com)
5-Vinylnorborn-2-ene is particularly interesting as a bifunctional monomer, because its norbornene double bond and pendant vinyl group can participate in chemically different reactions.
The strained endocyclic double bond is generally more reactive toward several polymerization systems, while the exocyclic vinyl group can remain available as a secondary functional site for later modification.
This difference in reactivity allows chemists to design polymers in which the main polymerization step and subsequent functionalization can be carried out separately.
5-Vinylnorborn-2-ene has been investigated in controlled vinyl-addition polymerization, where selective insertion of the norbornene double bond can produce poly(5-vinyl-2-norbornene) while preserving the pendant vinyl functionality.
Recent palladium-based work demonstrated that reaction temperature, solvent coordination, and catalyst design can influence chemoselectivity and help suppress unwanted insertion of the pendant vinyl group.
This provides a route toward polymers with more predictable molecular weights and narrower molecular-weight distributions.
5-Vinylnorborn-2-ene can also function differently in ring-opening metathesis polymerization, where its strained bicyclic alkene provides the driving force for opening the norbornene ring.
Research has shown that VNB can act as a reversible-deactivation chain-transfer monomer during ROMP, enabling the preparation of branched copolymers with controlled chain structures.
This makes the compound relevant to advanced polymer architectures where branching and chain topology need to be deliberately adjusted.
The ability to obtain different polymer structures from the same monomer is closely related to catalyst-dependent chemoselectivity.
Depending on the catalytic system, polymerization can preferentially involve the strained endocyclic alkene while leaving the pendant vinyl group intact, or reaction pathways involving the second alkene can become more significant.
Consequently, catalyst selection is an important consideration when VNB is used for the preparation of functional polymers.
5-Vinylnorborn-2-ene is being investigated as a platform for post-polymerization functionalization, because the remaining carbon–carbon double bonds provide convenient sites for further chemical reactions.
Reported transformations include hydrogenation, epoxidation, cyclopropanation, and thiol–ene modification, with high degrees of functionalization achieved while maintaining the polymer backbone.
These reactions can introduce substantially different chemical characteristics without requiring a completely new polymerization process.
Melting point: −80 °C (lit.)
Boiling point: 141 °C (lit.)
Density: 0.841 g/mL at 25 °C (lit.)
Vapor density: >1 (vs air)
Vapor pressure: 6 mm Hg at 20 °C
Refractive index: n20/D 1.481 (lit.)
Flash point: 82 °F
Storage temp.: 2-8 °C
Solubility: Soluble in methanol
Form: Liquid
Specific gravity: 0.841
Color: Clear
Viscosity: 1.103 mm²/s
Water solubility: 100 mg/L at 25 °C
InChI: InChI=1S/C9H12/c1-2-8-5-7-3-4-9(8)6-7/h2-4,7-9H,1,5-6H2/t7-,8,9-/m0/s1
InChIKey: INYHZQLKOKTDAI-SMOXQLQSSA-N
SMILES: C=CC1C[C@H]2C[C@@H]1C=C2
LogP: 3.39 at 20 °C
5-Vinylnorborn-2-ene, also referred to as 5-vinyl-2-norbornene (VNB), is a functionalized norbornene containing both a strained cyclic alkene and a pendant vinyl group.
The presence of two chemically distinct carbon–carbon double bonds gives the molecule greater synthetic flexibility than simple norbornene and allows different polymerization or functionalization pathways to be selected.
This dual unsaturation is particularly valuable in polymer chemistry because one alkene can participate in polymer formation while the other can remain available for subsequent modification.
The strained norbornene double bond is generally the more reactive site in ring-opening metathesis polymerization, while the pendant vinyl group can remain unreacted under suitable catalytic conditions.
This behavior allows polymers to be prepared with an unsaturated side-chain functionality that can subsequently be used for additional chemical transformations.
Such selective reactivity is one of the main reasons VNB is investigated as a multifunctional monomer for advanced polymer design.
5-Vinylnorborn-2-ene has been studied as a monomer for ring-opening metathesis polymerization (ROMP), a process in which the strained norbornene ring opens and forms a polymer backbone containing unsaturation.
Research has demonstrated that catalyst and solvent selection can strongly influence the selectivity of this polymerization and the products obtained from VNB.
The resulting polymers retain the pendant vinyl functionality under appropriate conditions, providing an additional site for post-polymerization chemistry.
5-Vinylnorborn-2-ene is also suitable for vinyl-addition polymerization, providing a different route to poly(5-vinyl-2-norbornene) materials.
In this polymerization mode, the norbornene double bond can be incorporated into the polymer backbone while the pendant vinyl group remains available for subsequent reactions.
This distinction between ring-opening and addition polymerization provides chemists with different approaches for controlling polymer architecture and final material properties.
Recent research has demonstrated the use of commercial 5-vinyl-2-norbornene as a reversible-deactivation chain-transfer monomer in ROMP.
This approach enables the preparation of branched copolymers with more controlled chain structures and allows the branch distribution to be influenced through polymerization conditions and comonomer selection.
The finding expands the potential role of VNB from a conventional functional monomer to a tool for designing more sophisticated polymer architectures.
Poly(5-vinyl-2-norbornene) is being investigated for gas-separation membrane applications because polynorbornene materials can combine rigid molecular structures with useful thermal and chemical resistance.
Studies have examined both homopolymers and copolymers containing VNB, as well as the influence of crosslinking and monomer composition on gas-transport behavior.
The permeability and selectivity of these materials can be adjusted through polymer composition and structural modification, making VNB relevant to membrane-material research.
The remaining double bonds in poly(5-vinyl-2-norbornene) provide opportunities for post-polymerization functionalization.
Reported modifications include hydrogenation, epoxidation, cyclopropanation, and thiol–ene reactions, with high degrees of functionalization achieved without destroying the polymer backbone.
These transformations can introduce polar or non-polar side groups and thereby modify properties such as gas permeability and separation selectivity.
Vinylnorbornene derivatives are also being investigated as building blocks for rigid alicyclic polyester materials.
Recent work used VNB as a precursor for alicyclic diols that can subsequently be incorporated into polyester structures designed to achieve high glass-transition temperatures and potentially serve as alternatives to conventional polycarbonate-type materials.
The reported scale-up experiments indicate that this chemistry is being considered beyond purely laboratory-scale molecular synthesis.
Another important feature of VNB is its ability to act as a multifunctional platform for sequential chemical modification.
The norbornene and vinyl functionalities do not necessarily have to be consumed in the same reaction, allowing researchers to design sequences in which polymerization is followed by selective modification of the remaining alkene.
This approach can be useful for preparing functional polymers whose chemical properties are introduced after the primary polymer structure has already been established.
5-Vinylnorborn-2-ene has also been investigated in copolymer systems, where its incorporation alongside norbornene or other functional monomers can modify the resulting polymer structure.
Changing the proportion of VNB can influence the number of pendant reactive groups available for later crosslinking or functionalization.
This provides an additional method for adjusting the properties of polynorbornene-based materials without changing the entire polymer backbone chemistry.
5-Vinylnorborn-2-ene has relevance to adhesion and cohesion-related applications, with chemical-use databases identifying vinylnorbornene among materials used as adhesion or cohesion promoters.
5-Vinylnorborn-2-enes reactive unsaturation can provide a route for incorporating the compound into more complex polymeric or surface-related structures.
These applications are more specialized than its established role in polymer research, so the suitability of a particular VNB grade depends on the formulation and polymerization process involved.
5-Vinylnorborn-2-ene has additionally been reported as a chain-transfer agent and chemical intermediate, reflecting the broader range of applications associated with its bifunctional structure.
Its ability to participate in controlled polymerization while retaining a second reactive alkene makes it useful for developing polymers with deliberately introduced branching or subsequent functionalization sites.
This is particularly relevant to specialty polymers where molecular architecture and post-polymerization modification are important performance parameters.
5-Vinylnorborn-2-ene is more than a conventional hydrocarbon monomer because its strained bicyclic alkene and pendant vinyl group provide two distinct chemical handles.
Current research connects the compound with ROMP, vinyl-addition polymerization, branched copolymers, gas-separation membranes, functionalized polynorbornenes, and rigid alicyclic polyester precursors.
For technical applications, the most relevant product characteristics are therefore not limited to purity but can also include the composition of the material, inhibitor content, and suitability for the specific polymerization or functionalization process.
Functionalized polymers derived from VNB have been examined for gas-separation membrane materials, particularly for separations involving carbon dioxide, methane, nitrogen, and hydrogen.
Changing the chemical nature of the pendant groups can alter both gas permeability and selectivity, allowing the membrane properties to be adjusted according to the desired separation.
This research demonstrates how the original bifunctional structure of VNB can ultimately be translated into tunable transport properties in polymeric materials.
5-Vinylnorborn-2-ene can therefore contribute to the development of polymers with high rigidity and controlled functionality, rather than simply acting as a conventional hydrocarbon monomer.
The norbornene framework provides a rigid cyclic structure, while the second alkene creates an additional chemical handle that can be retained, transformed, or incorporated into a more complex polymer architecture.
5-Vinylnorborn-2-ene combination is particularly attractive for specialty polymers where mechanical, thermal, optical, or chemical properties need to be tailored through molecular design.
The material is also relevant to copolymer synthesis, where VNB can be combined with norbornene derivatives or other functional monomers to introduce pendant reactive groups into the resulting material.
Changing the comonomer composition and polymerization conditions provides a way to control the concentration and distribution of these functional sites along the polymer chain.
Such copolymerization strategies are useful when a single monomer cannot provide the complete combination of properties required for a particular material.
The distinction between monomer purity and polymerization performance is especially important for VNB because catalytic polymerization can be sensitive to impurities and reaction conditions.
Water, oxygen, residual inhibitors, and other substances capable of interacting with the catalyst may influence conversion or molecular-weight control depending on the polymerization technology being used.
For this reason, technical procurement specifications should be matched to the actual catalyst system and process requirements instead of relying only on a general laboratory-grade specification.
Uses Of 5-Vinylnorborn-2-ene:
5-Vinylnorborn-2-ene was used in the preparation of 5-ethylidene-2-norbornene (ENB).
5-Vinylnorborn-2-ene is primarily used as a functional monomer in polymer chemistry, where its strained norbornene double bond provides a reactive site for polymerization while the pendant vinyl group can introduce additional functionality.
This combination allows the preparation of polymers that contain chemically accessible unsaturation for subsequent modification.
5-Vinylnorborn-2-ene is therefore particularly relevant to specialty polymer development rather than conventional commodity-polymer production. (pubs.acs.org)
One important application is ring-opening metathesis polymerization (ROMP), in which the strained norbornene ring opens to form a polymer backbone containing carbon–carbon double bonds.
5-Vinylnorborn-2-ene can be polymerized under suitable metathesis catalyst systems while retaining the pendant vinyl functionality for subsequent reactions.
This provides a practical route to functional polynorbornene materials with additional chemical handles. (sciencedirect.com)
5-Vinylnorborn-2-ene is also used in vinyl-addition polymerization to produce poly(5-vinyl-2-norbornene) and related materials.
In this approach, selective reaction at the norbornene double bond can leave the pendant vinyl group available for further functionalization after polymerization.
This provides an alternative polymerization strategy when maintaining pendant alkene functionality is important for the final material design. (sciencedirect.com)
5-Vinylnorborn-2-ene is used in the development of branched polymer architectures because the pendant vinyl functionality can participate in controlled chain-transfer or subsequent branching reactions.
Research has demonstrated its use as a reversible-deactivation chain-transfer monomer in ROMP, enabling the preparation of branched copolymers with controlled structural features.
This application is particularly relevant to advanced polymer synthesis where molecular topology affects the properties of the finished material. (pubs.acs.org)
The monomer is also employed in copolymer synthesis, where it can be combined with norbornene and other functional monomers to introduce pendant reactive groups into a polymer chain.
Adjusting the amount of VNB incorporated into the copolymer allows the concentration of these reactive sites to be controlled.
This approach can be used to tailor subsequent crosslinking, functionalization, and material properties. (pmc.ncbi.nlm.nih.gov)
Another application is the preparation of functionalized polynorbornene materials through post-polymerization modification.
The remaining unsaturated groups can undergo reactions such as hydrogenation, epoxidation, cyclopropanation, and thiol–ene functionalization.
These transformations allow the chemical properties of the polymer to be changed after polymerization without requiring a different monomer for every target material. (sciencedirect.com)
VNB-derived polymers are being investigated for gas-separation membranes, where chemical modification of the polymer can influence permeability and selectivity toward gases such as carbon dioxide, methane, nitrogen, and hydrogen.
The rigid norbornene-derived polymer structure provides a useful platform for developing membranes with controlled free volume and transport characteristics.
Post-polymerization functionalization can further adjust the interaction between the membrane material and the gases being separated. (pmc.ncbi.nlm.nih.gov)
5-Vinylnorborn-2-ene has also been used as a precursor for alicyclic monomers used in polyester synthesis.
VNB-derived alicyclic diols can be incorporated into polyester structures designed to provide rigid polymer backbones and elevated glass-transition temperatures.
This chemistry has attracted interest in the development of high-performance and potentially optically useful polymeric materials. (pubs.rsc.org)
5-Vinylnorborn-2-ene can serve as a building block for crosslinkable polymer systems, because its remaining alkene functionality provides a site for reactions between polymer chains or with multifunctional reagents.
Controlled crosslinking can convert initially soluble or thermoplastic materials into three-dimensional networks with different mechanical and chemical characteristics.
This makes VNB relevant to research into functional coatings, elastomeric materials, and polymer networks.
5-Vinylnorborn-2-ene is also useful in advanced polymer architecture, including the preparation of polymers with controlled branching and block structures.
Catalyst-controlled polymerization can determine which alkene participates in the reaction and how VNB is distributed within the resulting macromolecule.
Such control is important for materials research in which molecular weight, branching, composition, and functional-group density must be adjusted independently.
5-Vinylnorborn-2-ene is used in catalyst and polymerization research as a substrate for studying chemoselective reactions of multiple alkene functionalities.
Its two structurally different double bonds make it useful for evaluating whether a catalyst preferentially reacts with the strained norbornene alkene or the pendant vinyl group.
The resulting information can support the development of more selective polymerization and functionalization processes.
The compound is also relevant to specialty-materials research involving rigid alicyclic structures, where the norbornene framework can contribute structural rigidity while the pendant vinyl group provides a route for chemical modification.
This combination allows researchers to introduce additional functionality without completely changing the underlying molecular framework.
Such characteristics are useful when designing polymers for demanding thermal, mechanical, chemical, or separation-related applications.
In research-scale organic synthesis, 5-Vinylnorborn-2-ene can be used as a multifunctional starting material for selective alkene transformations.
The two double bonds can undergo hydrogenation, oxidation, addition, coupling, and other reactions under appropriately selected conditions, allowing access to structurally diverse norbornane derivatives.
This makes VNB useful as a synthetic platform in addition to its direct role as a polymer monomer.
The commercial value of 5-Vinylnorborn-2-ene therefore comes mainly from its role as a specialty monomer and functional chemical intermediate rather than from a single finished-product application.
Its documented uses span ROMP, vinyl-addition polymerization, copolymer and branched-polymer synthesis, post-polymerization functionalization, gas-separation membranes, and the preparation of rigid alicyclic polymer precursors.
For technical purchasing, the appropriate grade should be selected according to the intended polymerization method, catalyst system, purity, inhibitor concentration, and required isomer composition.
5-Vinylnorborn-2-ene can be used as a precursor for sulfur-containing functional materials because both of its carbon–carbon double bonds can undergo thiol-related transformations.
Patent literature describes its reaction with hydrogen sulfide to produce polythiol compositions containing norbornane-based thiol functionalities.
These products provide additional reactive groups that can subsequently be incorporated into polymer, adhesive, and other specialty-material formulations.
5-Vinylnorborn-2-ene is also being explored as a starting material for high-performance polyester development through conversion into alicyclic diol monomers.
VNB-derived diols have been investigated for preparing amorphous polyesters with rigid alicyclic structures and elevated glass-transition temperatures.
This route is of interest where thermal performance and structural rigidity are important requirements for the resulting polymer material.
Another application of VNB-derived polymers is the preparation of silicon-containing polynorbornene materials through post-polymerization hydrosilylation.
The remaining vinyl functionality of poly(5-vinyl-2-norbornene) can be modified with silicon-containing groups, producing polymers with improved solubility and new chemical characteristics.
Such materials have been investigated for membrane applications, microporous materials, and chromatographic stationary phases.
5-Vinylnorborn-2-ene can therefore serve as a platform for developing gas-storage and gas-separation materials rather than being limited to conventional polymer production.
Functionalized polynorbornene materials derived from VNB have been investigated for gas transport because their rigid structures can provide useful permeability and selectivity characteristics.
Modification of the pendant functionality provides an additional method for adjusting the interaction between the polymer and different gases.
5-Vinylnorborn-2-ene is useful in membrane-material research involving carbon dioxide separation, where chemical modification of polyvinylnorbornene can substantially change the balance between permeability and selectivity.
Studies have shown that hydrogenation and cyclopropanation can increase gas permeability, while epoxidation and thioacetylation can improve CO₂/N₂ selectivity at the expense of permeability.
This makes VNB-derived polymers an adaptable platform for investigating the relationship between polymer structure and membrane performance.
5-Vinylnorborn-2-ene is also used in research aimed at producing branched block copolymers with controlled molecular architectures.
Its use as a reversible-deactivation chain-transfer monomer in ROMP allows branching behavior to be adjusted through polymerization conditions and comonomer selection.
This application is relevant to specialty polymer design where molecular topology can influence viscosity, solubility, mechanical behavior, and other material properties.
5-Vinylnorborn-2-ene is consequently useful for preparing polymers with built-in post-functionalization sites.
After the primary polymerization step, the remaining alkene functionality can be modified without necessarily breaking down the polymer backbone, allowing properties to be adjusted after the material has already been formed.
This strategy can reduce the need to synthesize a separate monomer for every desired polymer functionality.
Another potential application lies in crosslinked polymer systems, where the additional vinyl functionality can provide reactive sites for network formation.
Crosslinking polyvinylnorbornene has been investigated as a way to modify gas-transport behavior and other material characteristics without completely changing the underlying polymer structure.
The concentration of VNB-derived functionality can therefore be used as one of the variables for controlling the final material properties.
5-Vinylnorborn-2-ene is also relevant to the development of functional polymer coatings and specialty materials, where pendant unsaturation can be converted into chemically active groups after polymer formation.
This allows the surface or bulk properties of a polymer to be modified through reactions such as hydrosilylation, epoxidation, thiol–ene chemistry, and related alkene transformations.
Such approaches are particularly useful when a polymer needs to combine a rigid backbone with chemically adjustable side functionality.
Safety Profile Of 5-Vinylnorborn-2-ene:
5-Vinylnorborn-2-ene is a flammable liquid and vapor, and its relatively low flash point means that vapors can ignite when the material is exposed to heat, sparks, flames, or other ignition sources.
Commercial safety information reports a flash point of approximately 27 °C, while other classifications identify the substance as highly flammable, so storage and handling should include effective ignition-source control and adequate ventilation.
During transfer operations, precautions against static discharge and the use of suitable explosion-protected equipment are important considerations.
Inhalation is an important occupational exposure route because VNB is a volatile liquid and its vapors can enter the breathing zone during open handling.
Available classifications range from harmful if inhaled to toxic if inhaled, depending on the supplier classification and material information used for the product.
For this reason, unnecessary inhalation of vapors should be avoided and handling should preferably take place under effective local exhaust ventilation or in a suitably enclosed process system.
Exposure to the skin can cause skin irritation, with current commercial classifications assigning the substance to Skin Irritation Category 2.
Repeated or prolonged contact should be avoided because the available safety information identifies direct skin exposure as a potential source of adverse effects.
Suitable chemical-resistant gloves and protective clothing should therefore be used when transferring, sampling, or otherwise handling the liquid.
5-Vinylnorborn-2-ene can also cause serious eye irritation, making eye protection an important part of routine handling procedures.
Splashes may produce irritation and discomfort, while the safety information recommends immediate and thorough rinsing if the substance enters the eyes.
Safety glasses with appropriate side protection or chemical splash goggles should be selected according to the exposure risk of the operation.
Some hazard classifications identify 5-Vinylnorborn-2-ene as presenting an aspiration hazard, meaning that swallowing the liquid followed by entry into the respiratory tract can result in serious consequences.
This classification is particularly relevant to accidental ingestion and should not be interpreted simply as ordinary gastrointestinal irritation.
Eating, drinking, or smoking should therefore be prohibited in areas where the substance is handled, with appropriate hygiene controls maintained.
5-Vinylnorborn-2-ene Procurement and Technical Support:
Ataman Kimya supports customers looking for 5-Vinylnorborn-2-ene with dependable supply solutions and relevant technical information for industrial and formulation requirements.
Additional support can be provided regarding product specifications, available documentation, and the evaluation of suitable product options based on the intended application.
