3048-64-4

Usage

Uses

Used in Adhesives Industry:
Vinylnorbornene is used as a monomer in the production of adhesives, contributing to their enhanced bonding strength and durability.
Used in Coatings Industry:
Vinylnorbornene serves as a key component in the synthesis of coatings, providing improved resistance to wear, corrosion, and environmental factors.
Used in Plastics Industry:
As a monomer, Vinylnorbornene is used in the production of various types of plastics, offering improved mechanical properties and thermal stability.
Used in Resin Manufacturing:
Vinylnorbornene is utilized in the manufacturing of specialized resins, which are essential for creating high-performance materials with specific properties tailored to various applications.
Used in Elastomer Production:
Vinylnorbornene is used as a crosslinking agent in rubber and elastomer formulations, enhancing their elasticity, strength, and resistance to deformation.
Used in Thermosetting Resins:
Vinylnorbornene is incorporated into the production of thermosetting resins, which are crucial for creating materials with exceptional heat resistance and dimensional stability.
Overall, Vinylnorbornene's diverse applications across various industries highlight its importance in the development of advanced materials with specific properties to meet the demands of modern industrial applications.

InChI:InChI=1/C9H12/c1-2-8-5-7-3-4-9(8)6-7/h2-3,8-9H,1,4-6H2

Synthetic route

5-Ethynylbicyclo<2.2.1>-2-heptene (77891-01-1) → 5-vinyl-2-norbornene (3048-64-4)

Conditions	Yield
With zinc/copper couple In diethyl ether; water at 45 - 50℃; for 40h;	95%

cyclopenta-1,3-diene (542-92-7) + buta-1,3-diene (106-99-0) → 5-vinyl-2-norbornene (3048-64-4)

Conditions	Yield
at 140 - 145℃;

bi(cyclopentadiene) (77-73-6, 933-60-8, 1755-01-7) + buta-1,3-diene (106-99-0) → bicyclo[4.3.0]nona-3,7-diene (3048-65-5) + 5-vinyl-2-norbornene (3048-64-4)

Conditions	Yield
at -20 - 205℃; for 1h; Temperature; Diels-Alder Cycloaddition; Autoclave; Inert atmosphere;	A 20 %Chromat. B 25 %Chromat.

cyclopenta-1,3-diene (542-92-7) + buta-1,3-diene (106-99-0) → bicyclo[4.3.0]nona-3,7-diene (3048-65-5) + 5-vinyl-2-norbornene (3048-64-4)

Conditions	Yield
In hexane at -20 - 205℃; for 1h; Solvent; Diels-Alder Cycloaddition; Autoclave; Inert atmosphere;	A 25 %Chromat. B 22 %Chromat.
at -20 - 205℃; for 1h; Temperature; Diels-Alder Cycloaddition; Autoclave; Inert atmosphere;	A 17 %Chromat. B 25 %Chromat.
Stage #1: cyclopenta-1,3-diene; buta-1,3-diene With N-ethyl-N-hydroxy-ethanamine In toluene under 26252.6 Torr; Flow reactor; Heating; Stage #2: at 115.4℃; under 195.02 - 240.024 Torr; Flow reactor;
In cyclohexane at 200℃; under 20686.5 Torr; for 0.166667h; Solvent; Inert atmosphere;

5-(1-methoxyethyl)bicyclo[2.2.1]hept-2-ene → 5-vinyl-2-norbornene (3048-64-4)

Conditions	Yield
With magnesium oxide In m-xylene at 200℃; under 760.051 Torr; for 3h;

cyclopenta-1,3-diene (542-92-7) + buta-1,3-diene (106-99-0) → bicyclo[4.3.0]nona-3,7-diene (3048-65-5) + 5-vinyl-2-norbornene (3048-64-4) + bi(cyclopentadiene) (77-73-6, 933-60-8, 1755-01-7)

Conditions	Yield
With evonik TS-1 zeolite catalyst In toluene at 200℃; under 20252 Torr; for 0.166667h; Reagent/catalyst; Diels-Alder Cycloaddition; Inert atmosphere;

5-vinyl-2-norbornene (3048-64-4) + Trichloroacetyl chloride (76-02-8) → 5-(2',2'-dichlorocyclobutan-3'-onyl)bicyclo<2.2.1>hept-2-ene

Conditions	Yield
With zinc In diethyl ether at 20 - 30℃; sonication;	95%

bromobenzene (108-86-1) + 5-vinyl-2-norbornene (3048-64-4) → (E)-5-styrylbicyclo[2.2.1]hept-2-ene

Conditions	Yield
Stage #1: bromobenzene With palladium diacetate; heptakis(6-amino-6-deoxy)-β-cyclodextrin In water; N,N-dimethyl-formamide for 0.5h; Stage #2: 5-vinyl-2-norbornene With potassium carbonate In water; N,N-dimethyl-formamide at 80℃; for 10h;	92%

trimethoxysilane (2487-90-3) + 5-vinyl-2-norbornene (3048-64-4) → (2-bicyclo[2.2.1]hept-5-en-2-yl-ethyl)-trimethoxy-silane (68323-30-8)

Conditions	Yield
With platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex; ammonium bicarbonate In toluene at 55 - 65℃; for 5h; Reagent/catalyst; Concentration;	91%

5-vinyl-2-norbornene (3048-64-4) → exo-2-chloro-6-ethenylbicyclo<2.2.1>heptane + exo-2-chloro-5-ethenylbicyclo<2.2.1>heptane

Conditions	Yield
With thionyl chloride; silica gel In dichloromethane for 0.25h; Title compound not separated from byproducts;	A 88% B n/a
With thionyl chloride; silica gel In dichloromethane for 0.25h; Title compound not separated from byproducts;	A n/a B 88%

5-vinyl-2-norbornene (3048-64-4) → 6-epoxyethyl-3-oxatricyclo<3.2.1.02,4>octane (2886-88-6)

Conditions	Yield
With potassium hydroxide; oxone In dichloromethane; acetone	85%
Stage #1: 5-vinyl-2-norbornene With water; hydrogen bromide; dihydrogen peroxide at 40℃; Stage #2: With potassium hydroxide In diethyl ether at 8 - 20℃; for 2.5h; Reagent/catalyst;	3.5 g

5-vinyl-2-norbornene (3048-64-4) → C36H48Cl8S4 (89913-95-1)

Conditions	Yield
With sulfur dichloride In dichloromethane at -7 - 0℃; for 1h;	78%

5-vinyl-2-norbornene (3048-64-4) → 5-ethylbicyclo[2.2.1]hept-2-ene (15403-89-1)

Conditions	Yield
With hydrogen; (η5-C5Me5)2YCH3(THF) In benzene under 760 Torr; for 2h; Ambient temperature;	72%

methanesulfonamide (3144-09-0) + 5-vinyl-2-norbornene (3048-64-4) → 1-(methylsulfonyl)octahydro-3a,6-methanoindole

Conditions	Yield
With trifluorormethanesulfonic acid at 85℃; for 14h; Inert atmosphere; Darkness; neat (no solvent);	70%

5-vinyl-2-norbornene (3048-64-4) + toluene-4-sulfonamide (70-55-3) → 1-tosyloctahydro-3a,6-methanoindole

Conditions	Yield
With (triphenyl phosphite)gold(I) chloride; silver trifluoromethanesulfonate at 90℃; for 0.5h; Inert atmosphere; Darkness; Microwave irradiation; air stream cooling; neat (no solvent);	70%

5-vinyl-2-norbornene (3048-64-4) + N-(1-phenylvinyl)acetamide (57957-24-1) → C17H18O

Conditions	Yield
With copper diacetate; palladium diacetate; triethylamine In dimethyl sulfoxide at 100℃;	70%

5-vinyl-2-norbornene (3048-64-4) → 5,5'-di(3-chloro-5-vinylbicyclo<2.2.1>heptyl) sulfide (89913-96-2) + C36H48Cl8S4 (89913-95-1)

Conditions	Yield
With sulfur dichloride In hexane at 5℃; for 36h;	A 51% B n/a

5-vinyl-2-norbornene (3048-64-4) → cis bicyclo<4.3.0>nona-3,7-diene (3048-65-5, 38451-18-2, 66563-20-0, 98102-87-5, 98102-88-6, 117179-82-5)

Conditions	Yield
at 250℃; for 0.533333h; Pressure (range begins): 200 ;	47%
Product distribution; different temperatures (180 to 250 deg C), different heating times; Pressure (range begins): 200 ;

5-vinyl-2-norbornene (3048-64-4) → 6-epoxyethyl-3-oxatricyclo<3.2.1.02,4>octane (2886-88-6) + 2,3-epoxy-5-vinylnorbornane (2886-87-5)

Conditions	Yield
With sodium hydroxide; dihydrogen peroxide; N-tosylimidazole In methanol for 3h;	A 11.5% B 29%

5-vinyl-2-norbornene (3048-64-4) → tetracyclo[4.2.1.0(2,5).0(3,7)]nonane (25557-71-5)

Conditions	Yield
In acetone; benzene Irradiation;

5-vinyl-2-norbornene (3048-64-4) → 2-ethylnorbornane (2146-41-0)

Conditions	Yield
With hydrogen; platinum
With hydrogen In methanol at 20℃; under 760.051 Torr; for 0.833333h; Reagent/catalyst;	> 99 %Chromat.

5-vinyl-2-norbornene (3048-64-4) → 5-ethylidene-2-norbornene (28304-67-8)

Conditions	Yield
With aluminum oxide; sodium In n-heptane at 0℃;
With aluminium(III) triflate; tricarbonylbis(triphenylphosphine)ruthenium(0) In toluene at 60℃; for 5h; Reagent/catalyst;	88.1 %Chromat.

5-vinyl-2-norbornene (3048-64-4) → 1-Vinyltricyclo<2.2.1.O2,6>heptane (4994-07-4)

Conditions	Yield
With aluminum oxide; sodium In n-heptane

5-vinyl-2-norbornene (3048-64-4) → 5-ethylidenebicyclo[2.2.1]hept-2-ene (28304-66-7)

Conditions	Yield
With aluminum oxide; sodium In n-heptane at 90℃;

5-vinyl-2-norbornene (3048-64-4) + buta-1,3-diene (106-99-0) → 2-Vinyl-1,4-endo-methylen-1,2,3,4,5,5a,8,8a-octahydro-naphthalin (66807-89-4, 66807-90-7, 37746-28-4)

Conditions	Yield
at 145 - 155℃;

formic acid (64-18-6) + 5-vinyl-2-norbornene (3048-64-4) → exo-6-vinylbicyclo<2.2.1>heptan-exo-2-ol (79657-39-9) + endo-5-vinylbicyclo<2.2.1>heptan-exo-2-ol (79703-61-0)

Conditions	Yield
With sodium hydroxide 1) 70 deg C, 4 h, 2) H2O-CH3OH, reflux, 2 h; Yield given. Multistep reaction. Title compound not separated from byproducts;

formic acid (64-18-6) + 5-vinyl-2-norbornene (3048-64-4) → 5-vinyl-2-norbornanone + 6-vinyl-2-norbornanone

Conditions	Yield
With chromium(VI) oxide; sulfuric acid 1) 70 deg C, 4 h, 2) H2O, 20 - 30 deg C, overnight; Multistep reaction. Title compound not separated from byproducts;
Multistep reaction. Title compound not separated from byproducts;

chloroform (67-66-3) + 5-vinyl-2-norbornene (3048-64-4) → 6-cyclopropylbicyclo<3.2.1>oct-2-ene (93794-74-2) + 7-cyclopropylbicyclo<3.2.1>oct-2-ene (93794-73-1)

Conditions	Yield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; lithium 1) H2O, 25 deg C, 4 h; 2) Et2O, tBuOH, reflux, 2 h; Multistep reaction;

chloroform (67-66-3) + 5-vinyl-2-norbornene (3048-64-4) → endo-6-cyclopropylbicyclo<3.2.1>octane (93794-75-3) + exo-6-cyclopropylbicyclo<3.2.1>octane (93794-75-3)

Conditions	Yield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; hydrogen; lithium; nickel 1) H2O, 25 deg C, 4 h; 2) Et2O, tBuOH, reflux, 2 h; 3) MeOH, 3 h; Multistep reaction;

5-vinyl-2-norbornene (3048-64-4) + sodium acetate (127-09-3) → exo-2-acetoxy-endo-5-chlorobrendane + exo-2-acetoxy-exo-5-chlorobrendane

Conditions	Yield
triphenylphosphine; copper(l) chloride; palladium dichloride In acetic acid at 80℃; for 24h; Yield given. Yields of byproduct given;

5-vinyl-2-norbornene (3048-64-4) → 5-ethylidene-2-norbornene (28304-67-8) + 5-ethylidenebicyclo[2.2.1]hept-2-ene (28304-66-7)

Conditions	Yield
γ-Al2O3-NaOH-Na at 25℃; for 3h; Product distribution;
γ-Al2O3-NaOH-Na at 25℃; for 3h; Yield given. Yields of byproduct given;
aluminum oxide; potassium amide at -0.1℃; for 0.166667h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

5-vinyl-2-norbornene (3048-64-4) → exo-2,3-epoxy-5-vinylbicylo<2.2.1>heptane (2886-87-5, 88424-89-9, 88424-90-2)

Conditions	Yield
With oxygen; Pd(MeCN)2Cl(NO2) In benzene at 60℃; for 144h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With phosphotungstic acid; cetylpyridinium chloride; dihydrogen peroxide In chloroform at 60℃; for 3h; Yield given;
With 4-tert-butylpyridine; potassium peroxomonosulfate; benzyldimethyltetradecylammonium chloride; (5,10,15,20-tetramesitylporphyrinato)manganese(III) chloride In phosphate buffer at 20℃; pH=7; Product distribution; Further Variations:; Catalysts; Reagents;	99 % Chromat.

5-vinyl-2-norbornene (3048-64-4) + acetic acid (64-19-7) → exo-2-acetoxy-endo-5-chlorobrendane + exo-2-acetoxy-exo-5-chlorobrendane

Conditions	Yield
With oxygen; lithium chloride; copper dichloride; palladium dichloride at 80℃; for 36h; Yield given. Yields of byproduct given;
With lithium chloride; copper dichloride; palladium dichloride at 80℃; for 36h; Yield given. Yields of byproduct given;

Upstream product

• 542-92-7 cyclopenta-1,3-diene 
• 106-99-0 buta-1,3-diene 
• 77891-01-1 5-Ethynylbicyclo<2.2.1>-2-heptene 
• 2065-66-9 methyl-triphenylphosphonium iodide 
• 5453-80-5 exo-2-formylbicyclo[2.2.1]hept-5-ene 
• 77-73-6 bi(cyclopentadiene) 
• 3048-64-4 5-vinyl-bicyclo[2.2.1]hept-2-ene 
• 3048-64-4 exo-vinylnorbornene 
• 3048-64-4 endo-vinylnorbornene 

Downstream Products

• 2146-41-0 2-ethylnorbornane 
• 28304-67-8 5-ethylidene-2-norbornene 
• 28304-66-7 5-ethylidene-2-norbornene 
• 3048-65-5 cis-bicyclo<4.3.0>nona-3,7-diene 
• 2886-87-5 exo-2,3-epoxy-5-vinylbicyclo[2.2.1]heptane 
• 2886-88-6 6-epoxyethyl-3-oxatricyclo<3.2.1.0^2,4>octane 
• 2886-87-5 2,3-epoxy-5-vinylnorbornane 
• 16859-58-8 5-epoxyethyl-2-norbornene 
• 475563-22-5 biperiden hydrochloride 
• 93778-71-3 C₁₅H₂₃NO 
• 163296-11-5 biperiden 
• 542-92-7 cyclopenta-1,3-diene 
• 106-99-0 buta-1,3-diene 
• 100-40-3 4-ethenylcyclohexene 

Relevant academic research and scientific papers

Synthesis of 5-vinyl-2-norbornene through Diels–Alder reaction of cyclopentadiene with 1,3-butadiene in supercritical carbon dioxide

An efficient method for the synthesis of 5-vinyl-2-norbornene from cyclopentadiene and 1,3-butadiene was developed. The Diels–Alder reaction of cyclopentadiene with 1,3-butadiene proceeded smoothly in supercritical carbon dioxide in the absence of any pol

Method for Production of 5-Vinyl-2-Norbornene Using Porous Titanosilicate Catalyst

The present invention relates to a method for manufacturing 5-vinyl-2-norbornene (VNB) by conducting reaction of cyclopentadiene (CPD) with 1,3-butadiene (BD). The method uses a porous titanosilicate catalyst, thereby providing an effect of increasing the selectivity of VNB and reducing the selectivity of by-product oligomer.(AA) CPD conversion ratio (%)(BB) VNB selectivity (%)(CC) THI selectivity (%)(DD) DCPD selectivity (%)(EE) Oligomer selectivity (%)(FF) Conversion ratio and selectivity (%)COPYRIGHT KIPO 2020

Method for Preparation of 5-Vinyl-2-Norbornene

The present invention relates to a method for preparing 5-vinyl-2-norbornene (VNB) by making cyclopentadiene (CPD) react with butadiene. The present invention uses a non-polar solvent having a relative polarity of 0.15 or less for a reaction, and thus can reduce selectivity of oligomers and THI, which are non-reusable byproducts, and increase the selectivity of 5-vinyl-2-norbornene.(AA) DCP pyrolysis(BB) VNB synthesis(CC) THI separation(DD) BD/CPD separation(EE) VCH separation(FF) VNB separationCOPYRIGHT KIPO 2020

METHOD OF PREPARING 5-VINYL-2-NORBORNENE THROUGH ALKOXYLATION

The present invention provides a method for producing 5-vinyl-2-norbornene with excellent selectivity and in high yield from cyclopentadiene and 1,3-butadiene using an alkoxylation reaction.COPYRIGHT KIPO 2020

Method for Production of 5-Vinyl-2-Norbornene Using Zeolite Catalyst substituted with Sn

The present invention relates to a method for producing 5-vinyl-2-norbornene (VNB) by inducing a Diels-Alder reaction of cyclopentadiene (CPD) and 1,3-butadiene (BD). The present invention provides an effect of increasing selectivity of 5-vinyl-2-norbornene and decreasing selectivity of an oligomer which is a byproduct by using a zeolite catalyst substituted with tin.(AA) CDP conversion ratio (%)(BB) VNB selectivity (%)(CC) THI selectivity (%)(DD) DCPD selectivity (%)(EE) Oligomer selectivity (%)(FF) Conversion ratio and selectivity (%)COPYRIGHT KIPO 2020

METHOD OF PREPARING 5-VINYL-2-NORBORNENE USING XYLENE AS SOLVENT

The present invention provides a method for preparing 5-vinyl-2-norbornene, comprising a step of making cyclopentadiene react with 1,3-butadiene in the presence of a xylene solvent. According to the present invention, the selectivity of 5-vinyl-2-norbornene and the yield thereof can be remarkably improved by using the xylene solvent.COPYRIGHT KIPO 2020

A multi-out live pressure tubular reactor synthetic vinyl norbornene

The invention discloses a method for synthesizing vinyl norbornene by using a one-inlet and multiple-outlet variable pressure type tubular reactor, wherein more than two discharge openings are formed in a reaction channel of the tubular reactor in the flowing direction of a material and the pressure is gradually decreased. The method comprises the following step: jointly inputting a cyclopentadiene solution and 1, 3-butadiene from a feed inlet at one time into the reaction channel of the tubular reactor so as to obtain the vinyl norbornene, wherein the reaction temperature of the reaction channel is 120-220 DEG C, the pressure is 20-2MPa and the standing time is 24-120 minutes, and the cyclopentadiene solution consists of cyclopentadiene, dicyclopentadiene and possible inert organic solvents. The invention belongs to a method for safely and efficiently synthesizing vinyl norbornene by using the one-inlet and multiple-outlet variable pressure type tubular reactor.

Through the multi-side live pressure tubular reactor synthesis method of the ethylidene norbornene

The invention discloses a method for synthesizing ethylidene norbornene by virtue of a multi-lateral-line pressure-variable tubular reactor. The reaction channel of the tubular reactor is provided with a starting material inlet and at least two lateral-line material inlets and the pressure is reduced gradually. The method comprises the following steps: 1) feeding a cyclopentadiene solution into the reaction channel of the tubular reactor from the starting material inlet and feeding 1,3-butadiene into the reaction channel of the tubular reactor from the starting material inlet and any one or more lateral-line material inlets, enabling the cyclopentadiene solution and 1,3-butadiene to have a Diels-Alder addition reaction in the reaction channel of the tubular reactor to obtain vinyl norbornene; 2) performing isomerization on the obtained vinyl norbornene in the tubular reactor subsequently filled with a super basic catalyst to obtain ethylidene norbornene, wherein the reaction temperature is between -10 DEG C and 50 DEG C and the dwell time is 10-69min.

5-ethylidene-2-norborene ENB method for the production of (by machine translation)

The invention relates to a production method for ENB (5-ethylene-2-norbornylene) and mainly aims to solve the problems in the prior art that the purity of a product is low and the energy consumption is high. The adopted production method for the ENB comprises the following steps: (1) raw materials and a solvent are sent to a first reaction vessel through a static mixer; (2) the reaction product in the first reaction vessel enters into a light component removing tower, tower top light components return to the first reaction vessel and tower kettle heavy components enter into a heavy component removing tower; (3) the kettle components of the heavy component removing tower enter into a DCPD tower, and tower top distilled liquid is purified to obtain a DCPD product; (4) the heavy component removing tower kettle components enter into a VCH tower, the VCH is obtained at the tower top; tower kettle components enter into a VNB tower, THI is obtained in a VNB tower kettle and the VNB is obtained at the tower top; (5) VNB enters into an isomerization reaction vessel to obtain ENB. The problems are better solved by the technical scheme and the production method can be applied in the ENB production.

Ultrahigh Tg Epoxy Thermosets Based on Insertion Polynorbornenes

Thermosetting materials (thermosets) are widely used organic materials derived from 3D-network forming monomers. Achieving high glass transition temperature (Tg) thermosets is often a challenging task due to the complexity of designing efficiently and cheaply monomers which are rigid enough to prevent molecular motions within the thermoset. We report here a very simple route to prepare epoxy thermosets with Tg as high as 350 °C, based on insertion polynorbornenes. The epoxy monomer (PNBE(epoxy)) is prepared by the epoxidation of poly(5-vinylnorbornene) obtained by catalytic insertion polymerization of 5-vinylnorbornene. PNBE(epoxy) can be cross-linked with simple biosourced compounds. Alternatively, polar insertion polynorbornene can also be used as cross-linker in the formulation of an epoxy resin, once again resulting in epoxy resins with Tg higher than 300 °C and devoid of degradation at this temperature. Thus, this study clearly demonstrates the viability of catalytic polymerization to access epoxy thermosets with ultrahigh Tg.