5-Ethynylbicyclo<2.2.1>-2-heptene
5-vinyl-2-norbornene
Conditions | Yield |
---|---|
With zinc/copper couple In diethyl ether; water at 45 - 50℃; for 40h; | 95% |
Conditions | Yield |
---|---|
at 140 - 145℃; |
bi(cyclopentadiene)
buta-1,3-diene
A
bicyclo[4.3.0]nona-3,7-diene
B
5-vinyl-2-norbornene
Conditions | Yield |
---|---|
at -20 - 205℃; for 1h; Temperature; Diels-Alder Cycloaddition; Autoclave; Inert atmosphere; | A 20 %Chromat. B 25 %Chromat. |
cyclopenta-1,3-diene
buta-1,3-diene
A
bicyclo[4.3.0]nona-3,7-diene
B
5-vinyl-2-norbornene
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-vinyl-2-norbornene
Conditions | Yield |
---|---|
With magnesium oxide In m-xylene at 200℃; under 760.051 Torr; for 3h; |
cyclopenta-1,3-diene
buta-1,3-diene
A
bicyclo[4.3.0]nona-3,7-diene
B
5-vinyl-2-norbornene
C
bi(cyclopentadiene)
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; |
Conditions | Yield |
---|---|
With zinc In diethyl ether at 20 - 30℃; sonication; | 95% |
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
5-vinyl-2-norbornene
(2-bicyclo[2.2.1]hept-5-en-2-yl-ethyl)-trimethoxy-silane
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
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% |
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
C36H48Cl8S4
Conditions | Yield |
---|---|
With sulfur dichloride In dichloromethane at -7 - 0℃; for 1h; | 78% |
5-vinyl-2-norbornene
5-ethylbicyclo[2.2.1]hept-2-ene
Conditions | Yield |
---|---|
With hydrogen; (η5-C5Me5)2YCH3(THF) In benzene under 760 Torr; for 2h; Ambient temperature; | 72% |
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid at 85℃; for 14h; Inert atmosphere; Darkness; neat (no solvent); | 70% |
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% |
Conditions | Yield |
---|---|
With copper diacetate; palladium diacetate; triethylamine In dimethyl sulfoxide at 100℃; | 70% |
5-vinyl-2-norbornene
A
5,5'-di(3-chloro-5-vinylbicyclo<2.2.1>heptyl) sulfide
B
C36H48Cl8S4
Conditions | Yield |
---|---|
With sulfur dichloride In hexane at 5℃; for 36h; | A 51% B n/a |
5-vinyl-2-norbornene
cis bicyclo<4.3.0>nona-3,7-diene
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
6-epoxyethyl-3-oxatricyclo<3.2.1.02,4>octane
B
2,3-epoxy-5-vinylnorbornane
Conditions | Yield |
---|---|
With sodium hydroxide; dihydrogen peroxide; N-tosylimidazole In methanol for 3h; | A 11.5% B 29% |
5-vinyl-2-norbornene
tetracyclo[4.2.1.0(2,5).0(3,7)]nonane
Conditions | Yield |
---|---|
In acetone; benzene Irradiation; |
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
5-ethylidene-2-norbornene
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. |
Conditions | Yield |
---|---|
With aluminum oxide; sodium In n-heptane |
5-vinyl-2-norbornene
5-ethylidenebicyclo[2.2.1]hept-2-ene
Conditions | Yield |
---|---|
With aluminum oxide; sodium In n-heptane at 90℃; |
5-vinyl-2-norbornene
buta-1,3-diene
2-Vinyl-1,4-endo-methylen-1,2,3,4,5,5a,8,8a-octahydro-naphthalin
Conditions | Yield |
---|---|
at 145 - 155℃; |
formic acid
5-vinyl-2-norbornene
A
exo-6-vinylbicyclo<2.2.1>heptan-exo-2-ol
B
endo-5-vinylbicyclo<2.2.1>heptan-exo-2-ol
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; |
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
5-vinyl-2-norbornene
A
6-cyclopropylbicyclo<3.2.1>oct-2-ene
B
7-cyclopropylbicyclo<3.2.1>oct-2-ene
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
5-vinyl-2-norbornene
endo-6-cyclopropylbicyclo<3.2.1>octane
exo-6-cyclopropylbicyclo<3.2.1>octane
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; |
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
A
5-ethylidene-2-norbornene
B
5-ethylidenebicyclo[2.2.1]hept-2-ene
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
exo-2,3-epoxy-5-vinylbicylo<2.2.1>heptane
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. |
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; |
Product Name: 5-Vinyl-2-norbornene (CAS NO.3048-64-4)
Molecular Formula: C9H12
Molecular Weight: 120.19g/mol
Mol File: 3048-64-4.mol
Einecs: 221-259-8
Appearance: Clear liquid
Melting Point: −80 °C(lit.)
Boiling point: 141 °C at 760 mmHg
Storage Temperature: 0-6°C
Flash Point: 26.2 °C
Density: 0.841 g/mL at 25 °C(lit.)
Refractive index: n20/D 1.481(lit.)
Surface Tension: 37.3 dyne/cm
Enthalpy of Vaporization: 36.26 kJ/mol
Vapour Pressure: 7.47 mmHg at 25°C
XLogP3-AA: 2.7
H-Bond Donor: 0
H-Bond Acceptor: 0
Product Categories: Acyclic; Alkenes; Organic Building Blocks
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LC50 | inhalation | 17700mg/m3/2H (17700mg/m3) | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 18(10), Pg. 52, 1974. | |
mouse | LD50 | oral | 5667mg/kg (5667mg/kg) | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 18(10), Pg. 52, 1974. | |
rabbit | LD50 | skin | 15900uL/kg (15.9mL/kg) | American Industrial Hygiene Association Journal. Vol. 30, Pg. 470, 1969. | |
rat | LC50 | inhalation | 2231ppm/4H (2231ppm) | PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE BEHAVIORAL: TREMOR BEHAVIORAL: ATAXIA | National Technical Information Service. Vol. OTS0536315, |
rat | LD50 | oral | 5190uL/kg (5.19mL/kg) | American Industrial Hygiene Association Journal. Vol. 30, Pg. 470, 1969. |
Reported in EPA TSCA Inventory.
Mildly toxic by ingestion, inhalation, and skin contact. When heated to decomposition it emits acrid smoke and irritating fumes.
Safety Information of 5-Vinyl-2-norbornene (CAS NO.3048-64-4):
Hazard Codes: Xi
Risk Statements: 10-36/38
10: Flammable
36: Irritating to the eyes
38: Irritating to the skin
Safety Statements: 16-26-36/37
16: Keep away from sources of ignition - No smoking
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36: Wear suitable protective clothing
37: Wear suitable gloves
5-Vinyl-2-norbornene ,its CAS NO. is 3048-64-4,the synonyms is 2-Norbornene, 5-vinyl- ; 2-Norbornene,5-vinyl-[qr] ; 2-Vinyl-5-norbornene ; 2-Vinylbicyclo[2.2.1]hept-5-ene ; 2-Vinylnorbornene ; 2-Vinylnorbornene[qr] ; 5-Ethenyl-bicyclo(2.2.1)hept-2-en ; 5-Ethenyl-bicyclo(2.2.1)hept-2-ene .
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