3048-64-4

Basic information

• Product Name: Vinylnorbornene
• Synonyms: 2-Norbornene,5-vinyl- (6CI,7CI,8CI); 2-Vinyl-5-norbornene; 2-Vinylbicyclo[2.2.1]hept-5-ene;2-Vinylnorbornene; 5-Ethenylbicyclo[2.2.1]hept-2-ene; 5-Vinyl-2-norbornene;5-Vinylbicyclo[2.2.1]hept-2-ene; 5-Vinylnorbornene; NSC 61529; V 0062; VBH;Vinylnorbornene
• CAS NO: 3048-64-4
• Molecular Formula: C₉H₁₂
• Molecular Weight: 120.21
• EINECS: 221-259-8
• Mol File: 3048-64-4.mol
• Article Data: 22

Chemical Properties

• Melting Point: -80℃
• Boiling Point: 141°Cat760mmHg
• Flash Point: 26.2°C
• Appearance: /
• Density: 1.006g/cm³
• Vapor Pressure: 304
• Refractive Index: 144.1732
• CAS DataBase Reference: Vinylnorbornene(CAS DataBase Reference)
• NIST Chemistry Reference: Vinylnorbornene(3048-64-4)
• EPA Substance Registry System: Vinylnorbornene(3048-64-4)

Safety Data

• Hazard Codes: Xn:Harmful
• Statements: R10:Flammable.; R20:Harmful by inhalation.; R36/38:Irritating to eyes and skin.
• Safety Statements: S16:Keep away from sources of ignition - No smoking.; S26:In case of contact with eyes, rinse immediately with plenty of
• Hazardous Substances Data: 3048-64-4(Hazardous Substances Data)

Usage

General Description

Vinylnorbornene, also known as vinylbicyclo[2.2.1]hept-2-ene, is a chemical compound used in the production of various materials such as adhesives, coatings, and plastics. It is a colorless liquid with a pungent odor and is highly flammable. Vinylnorbornene is primarily used as a monomer in the synthesis of polymers, particularly in the manufacturing of specialized resins and elastomers. It is also utilized in the production of thermosetting resins and as a crosslinking agent in rubber and elastomer formulations. Due to its versatile chemical properties and reactivity, vinylnorbornene is a valuable component in the development of advanced materials with desirable mechanical and thermal properties for a wide range of 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

• 2065-66-9 methyl-triphenylphosphonium iodide 
• 5453-80-5 exo-2-formylbicyclo[2.2.1]hept-5-ene 
• 542-92-7 cyclopenta-1,3-diene 
• 106-99-0 buta-1,3-diene 
• 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 
• 77891-01-1 5-Ethynylbicyclo<2.2.1>-2-heptene 

Downstream Products

• 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 
• 5063-03-6 2-acetyl-5-norbornene 
• 83988-54-9 2-(5-norbornen-endo-2-yl)ethyl p-toluenesulfonate 
• 3048-64-4 5-vinyl-8,9,10-trinorborn-2-ene 
• 542-92-7 cyclopenta-1,3-diene 
• 106-99-0 buta-1,3-diene 
• 100-40-3 4-ethenylcyclohexene 
• 3048-65-5 bicyclo[4.3.0]nona-3,7-diene 
• 3048-64-4 5-vinyl-2-norbornene 

Relevant articles and documents

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 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