exo-3-(trimethylsilyl)-endo-2-norbornyl trifluoroacetate
norborn-2-ene
Conditions | Yield |
---|---|
With water In acetone at 65.1℃; Kinetics; Product distribution; Rate constant; | 98% |
norborn-2-ene
Conditions | Yield |
---|---|
In methanol electrochemical oxidation; | 96% |
A
norborn-2-ene
B
benzophenone
C
1,1-Diphenylmethanol
D
1,1-diphenylmethylenenorbornane
Conditions | Yield |
---|---|
at 290℃; for 3h; | A 27% B 95% C 15% D 64% |
exo-2,3-epoxynorbornane
norborn-2-ene
Conditions | Yield |
---|---|
With polystyrene-supported(catecholato)oxoRe cat. act. by iPrOH; triphenylphosphine In toluene for 8h; Heating; | 92% |
norborn-2-ene
Conditions | Yield |
---|---|
With lithium triethylborohydride In tetrahydrofuran at 60℃; for 4h; | 85% |
exo-2,3-epoxynorbornane
norborn-2-ene
Conditions | Yield |
---|---|
With triphenylphosphine at 200℃; for 8.5h; Product distribution; | 84% |
endo-3-(Trimethylsilyl)bicyclo<2.2.1>heptan-endo-2-carbonsaeure
norborn-2-ene
Conditions | Yield |
---|---|
In ethanol; acetonitrile at 60℃; anodic oxidation; | 60% |
With potassium hydroxide In ethanol; acetonitrile at 60℃; electrolysis: C-anode, Pt-catode; | 60 % Chromat. |
ethanol
Potassium; (1R,2S,3R,4S)-3-trimethylsilanyl-bicyclo[2.2.1]heptane-2-carboxylate
A
norborn-2-ene
2-(trimethylsilyl)bicyclo[2.2.1]hept-2-ene
((1R,2R,3R,4S)-3-Ethoxy-bicyclo[2.2.1]hept-2-yl)-trimethyl-silane
Conditions | Yield |
---|---|
In acetonitrile at 0℃; Product distribution; anidic decarboxylation, other solvens, temperature; | A 51% B 14% C 17% |
C14H15N2O2S(1-)*Na(1+)
A
norborn-2-ene
B
Bicyclo<3.2.0>heptadien-1,6
C
toluene
D
spiro[2.4]hepta-4,6-diene
Conditions | Yield |
---|---|
at 275℃; under 0.0001 - 0.0004 Torr; | A 2.7% B 51% C 0.9% D 4.9% |
2-endo-(Dichloroamino)norbornane
A
norborn-2-ene
B
2-(Chloroimino)norbornane
Conditions | Yield |
---|---|
A 12% B 50% |
2-exo-(Dichloroamino)norbornane
A
norborn-2-ene
B
2-(Chloroimino)norbornane
Conditions | Yield |
---|---|
A 11% B 48% |
methyllithium
7,7-dibromo-2-norbornene
A
norborn-2-ene
B
syn-7-bromobicyclo<2.2.1>heptene
C
Bicyclo<3.2.0>heptadien-1,6
D
syn-7-bromo-7-methylnorbornene
E
spiro[2.4]hepta-4,6-diene
Conditions | Yield |
---|---|
at 100℃; under 0.005 Torr; Product distribution; other reaction conditions; | A 0.1% B 20.5% C 47.5% D 6.6% E 12.6% |
methanol
Potassium; (1R,2S,3R,4S)-3-trimethylsilanyl-bicyclo[2.2.1]heptane-2-carboxylate
A
norborn-2-ene
2-(trimethylsilyl)bicyclo[2.2.1]hept-2-ene
((1R,2R,3R,4S)-3-Methoxy-bicyclo[2.2.1]hept-2-yl)-trimethyl-silane
Conditions | Yield |
---|---|
In acetonitrile at 0℃; Product distribution; anidic decarboxylation, other solvens, temperature; | A 19% B 17% C 44% |
Conditions | Yield |
---|---|
In tetrahydrofuran; pentane at 25℃; | A 38% B 44% |
α-chloronorbornene
A
norborn-2-ene
Conditions | Yield |
---|---|
With tert.-butyl lithium In tetrahydrofuran; pentane at 25℃; | A 38% B 44% |
Conditions | Yield |
---|---|
at 190℃; under 0.05 Torr; for 2h; Pyrolysis; | A 38.7% B 8.3% C 9.2% D 41.8% |
Conditions | Yield |
---|---|
With copper(II) bis(trifluoromethanesulfonate) | 32% |
norborn-2-ene
Conditions | Yield |
---|---|
With copper(II) bis(trifluoromethanesulfonate) | 30% |
Conditions | Yield |
---|---|
at 190 - 200℃; under 73550.8 - 117681 Torr; |
norbornyl chloride
norborn-2-ene
Conditions | Yield |
---|---|
With quinoline |
norborn-2-ene
cis-cyclopentane-1,3-dicarboxaldehyde
Conditions | Yield |
---|---|
With potassium permanganate; copper(II) sulfate; tert-butyl alcohol In dichloromethane; water at 22℃; for 12h; | 100% |
With sodium periodate; ruthenium In water; 1,2-dichloro-ethane at 20℃; for 3h; | 72% |
With ruthenium trichloride; Oxone; sodium hydrogencarbonate In water; acetonitrile at 20℃; for 0.7h; | 72% |
norborn-2-ene
exo-2,3-epoxynorbornane
Conditions | Yield |
---|---|
With pyridine N-oxide; oxochromium(V) complex of tetramethylsalen IIb In acetonitrile | 100% |
With cobalt(III) acetylacetonate; oxygen In tetrahydrofuran at 70℃; for 24h; | 98% |
With [2-percarboxyethyl] functionalized silica In dichloromethane at 20℃; for 1h; | 95% |
norborn-2-ene
Phenylselenyl chloride
endo-3-chloro-exo-2-phenylselenobicyclo<2.2.1>heptane
Conditions | Yield |
---|---|
In dichloromethane | 100% |
In water; acetonitrile for 24h; Ambient temperature; | 84% |
In dichloromethane at 25℃; | 100 % Spectr. |
norborn-2-ene
ethyl chloro(2-phenylhydrazono)acetate
Conditions | Yield |
---|---|
With triethylamine In chloroform for 2h; Heating; | 100% |
norborn-2-ene
2-diazo-4,5-dicyano-2H-imidazole
(5aα,6β,9β,9aα)-5a,6,7,8,9,9a-hexahydro-6,9-methanoimidazo<2,1-c><1,2,4>benzotriazine-1,2-dicarbonitrile
Conditions | Yield |
---|---|
In dichloromethane at -15℃; for 360h; | 100% |
norborn-2-ene
4-methyl-5-methylidene-4-phenyl-1,3-dioxolan-2-one
Conditions | Yield |
---|---|
tetrakis(triphenylphosphine) palladium(0) In toluene for 15h; Mechanism; Heating; other substrates, other alkenes, other catalysts; | 100% |
tetrakis(triphenylphosphine) palladium(0) In toluene for 15h; Heating; | 100% |
Conditions | Yield |
---|---|
With hemin polymer (1); 1,2,3,4,5-pentafluoro-6-iodosylbenzene In dichloromethane; water for 0.05h; | 100% |
With 3-chloro-benzenecarboperoxoic acid; iron(III) perchlorate In acetonitrile at -10℃; for 0.0833333h; | 100% |
With oxygen; isobutyraldehyde In acetonitrile at 40℃; for 6h; | 99% |
Conditions | Yield |
---|---|
With 1-Thia-3,4-diazolidine-2,5-dione In various solvent(s) Ambient temperature; Irradiation; | 100% |
With {(η6-C6H6)Ru(NCCH3)3}{BF4}2; water; hydrogen In benzene at 90℃; under 30400 Torr; for 4h; | 100% |
With C28H18Co(1-)*K(1+)*2C4H10O2; hydrogen In toluene at 60℃; under 1500.15 Torr; for 24h; chemoselective reaction; | 100% |
norborn-2-ene
exo,exo-2,3-dideuterionorbornane
Conditions | Yield |
---|---|
With deuterium; Wilkinson's catalyst In toluene | 100% |
With lithium aluminium deuteride; deuteropropionic acid; boron trifluoride diethyl etherate 1.) diglyme, 1 h, RT; 2.) diglyme, 140 deg C, 2 h; Yield given. Multistep reaction; | |
With deuterium; (iPrPDI)Fe(N2)2 at 22℃; under 760 Torr; | |
With BF4(1-)*C30H42N3PRh(1+); deuterium at 110℃; under 2585.81 Torr; for 24h; Inert atmosphere; Autoclave sealed; | |
With tetrahydroxydiborane(4); palladium 10% on activated carbon; water-d2 In dichloromethane at 20℃; for 5h; Mechanism; Inert atmosphere; Glovebox; |
norborn-2-ene
exo-2-trichlorosilylnorbornane
Conditions | Yield |
---|---|
With (Ra)-(2'-methoxy-[1,1']-binaphthalenyl-2-yl)-diphenylphosphine; trichlorosilane; bis(η3-allyl-μ-chloropalladium(II)) at 0℃; for 24h; Product distribution; other bicycloalkenes, stereoselectivity; | 100% |
With trichlorosilane; (Ra)-(2'-methoxy-[1,1']-binaphthalenyl-2-yl)-diphenylphosphine; bis(η3-allyl-μ-chloropalladium(II)) at -20℃; for 72h; | 99% |
norborn-2-ene
carbon monoxide
hex-1-yne
(3aSR,4SR,7RS,7aSR)-2-butyl-3a,4,5,6,7,7a-hexahydro-4,7-methanoinden-1-one
Conditions | Yield |
---|---|
dodecacarbonyl tetracobalt In dichloromethane at 150℃; under 7600 Torr; for 22h; | 100% |
Co2Rh2 nanoparticles immobilized on charcoal In tetrahydrofuran at 130℃; under 760 Torr; for 18h; intermolecular Pauson-Khand reaction; | 60% |
norborn-2-ene
1-decyne
carbon monoxide
(3aR,4R,7S,7aR)-2-Octyl-3a,4,5,6,7,7a-hexahydro-4,7-methano-inden-1-one
Conditions | Yield |
---|---|
With 1,2-dimethoxyethane; dicobalt octacarbonyl In toluene at 120℃; under 5320 Torr; for 10h; | 100% |
With cobalt(II) bromide; zinc In toluene; tert-butyl alcohol 25 deg C, 5 h; 110 deg C, 24 h; | 85% |
norborn-2-ene
Conditions | Yield |
---|---|
In 2,2,4-trimethylpentane Heating; | 100% |
norborn-2-ene
Conditions | Yield |
---|---|
With polymer-supported 4-methylmorpholine-N-oxide In dichloromethane at 20℃; for 2.5h; Cycloaddition; Pauson-Khand reaction; | 100% |
With morpholine N-oxide resin In tetrahydrofuran at 20℃; for 0.5h; Cycloaddition; Pauson-Khand reaction; | 91% |
norborn-2-ene
Conditions | Yield |
---|---|
Stage #1: norborn-2-ene; N-((1R,2S,4R)-4-Bicyclo[2.2.1]hept-5-en-2-yl-benzenesulfonylmethyl)-formamide; Grubbs catalyst first generation In dichloromethane at 20℃; for 0.5h; Stage #2: With ethyl vinyl ether Further stages.; | 100% |
norborn-2-ene
bis(pinacol)diborane
Conditions | Yield |
---|---|
With tris(bicyclo[2.2.1]heptene)palladium; triphenylphosphine at 20℃; for 2h; | 100% |
norborn-2-ene
Conditions | Yield |
---|---|
[=CHPh][1,3-(PhEt)2-2-imidazolinylidene][1-(2Py)Pr-2-O]RuCl2 In toluene at 60℃; for 0.25h; Product distribution; Further Variations:; Catalysts; Temperatures; Solvents; | 100% |
With Allyl acetate; C45H84Cl2P2RuSi In toluene at 40℃; | 99% |
With Allyl acetate; Grubbs catalyst first generation In toluene at 40℃; | 99% |
norborn-2-ene
Conditions | Yield |
---|---|
[2-methyliminomethyl-4-nitrophenol][PCy3][=CHPh]RuCl In chlorobenzene at 70℃; for 4h; Product distribution; Further Variations:; Catalysts; | 100% |
norborn-2-ene
Conditions | Yield |
---|---|
Schiff base substituted ruthenium benzylidene; 1,3-bis(2,4,6-trimethylphenyl)imidazolidin-2-ylidene In toluene at 70℃; for 4h; ring-opening metathesis polymerization; | 100% |
norborn-2-ene
iodobenzene
exo-2-phenylbicyclo[2.2.1]heptane
Conditions | Yield |
---|---|
With formic acid; triethylamine; [Pd(Cl)(L-κ-C,N,N)] In dimethyl sulfoxide at 90℃; for 15h; Heck hydroarylation; | 100% |
With formic acid; chloro[2-(3-methyl-3,7-diazabicyclo[3.3.1]nonan-3-ylmethyl)phenyl-C,N,N]palladium; triethylamine In dimethyl sulfoxide at 65℃; for 5h; | 99% |
With formic acid; C19H23ClFeN2OPd; triethylamine In dimethyl sulfoxide at 65℃; for 5h; Heck Reaction; | 97% |
With formic acid; 3-(2-(diphenylarsinyl)benzyl)-1-phenyl-1H-imidazol-3-ium chloride; triethylamine; bis(dibenzylideneacetone)-palladium(0) In dimethyl sulfoxide at 60℃; for 22h; Heck reaction; Inert atmosphere; | 86% |
With formic acid; C18H12Cl2N2O2Pd; triethylamine In dimethyl sulfoxide at 65℃; for 5h; | 77% |
norborn-2-ene
Conditions | Yield |
---|---|
With (2,6-(2,6-iPr2C6H3N=CMe)2C5H3N)MoCl3; triethylaluminum In toluene at 25℃; for 6h; | 100% |
norborn-2-ene
Conditions | Yield |
---|---|
With (2,6-(2,6-iPr2C6H3N=CMe)2C5H3N)MoCl3; triethylaluminum In toluene at 60℃; for 6h; | 100% |
norborn-2-ene
Conditions | Yield |
---|---|
With (2,6-(2,6-iPr2C6H3N=CMe)2C5H3N)MoCl3; triethylaluminum In toluene at 25℃; for 6h; | 100% |
norborn-2-ene
Conditions | Yield |
---|---|
With (2,6-(2,6-iPr2C6H3N=CMe)2C5H3N)MoCl3; triethylaluminum In toluene at 60℃; for 6h; | 100% |
norborn-2-ene
Conditions | Yield |
---|---|
With 2,6-bis[1-(2,6-diethylphenylimino)ethyl]pyridine-MoCl3; triethylaluminum In toluene at 25℃; for 6h; | 100% |
norborn-2-ene
Conditions | Yield |
---|---|
With 2,6-bis[1-(2,6-diethylphenylimino)ethyl]pyridine-MoCl3; triethylaluminum In toluene at 60℃; for 6h; | 100% |
norborn-2-ene
Conditions | Yield |
---|---|
With (2,6-(2,6-iPr2C6H3N=CMe)2C5H3N)MoCl3; modified methylaluminoxane with AlMeO:Al-isoBuO In toluene at 60℃; for 12h; | 100% |
Molecular Structure of Norbornylene (498-66-8):
EINECS: 207-866-0
IUPAC Name: Bicyclo[2.2.1]hept-2-ene
Molecular Formula: C7H10
Molecular Weight: 94.154300 g/mol
XLogP3-AA: 2.4
H-Bond Donor: 0
H-Bond Acceptor: 0
Canonical SMILES: C1CC2CC1C=C2
InChI: InChI=1S/C7H10/c1-2-7-4-3-6(1)5-7/h1-2,6-7H,3-5H2
InChIKey: JFNLZVQOOSMTJK-UHFFFAOYSA-N
Index of Refraction: 1.519
Molar Refractivity: 29.93 cm3
Molar Volume: 98.5 cm3
Surface Tension: 35.4 dyne/cm
Density: 0.955 g/cm3
Enthalpy of Vaporization: 32.17 kJ/mol
Boiling Point: 96 °C at 760 mmHg
Vapour Pressure: 50.7 mmHg at 25 °C
Melting Point: 44-46 °C(lit.)
Water Solubility: 60.32 mg/L at 25 °C
Storage Temp.: 0-6 °C
BRN: 1098544
1. | orl-rat LD50:11,300 mg/kg | AIHAAP American Industrial Hygiene Association Journal. 30 (1969),470. |
Reported in EPA TSCA Inventory.
Safety Information of Norbornylene (498-66-8):
Hazard Codes: F
Risk Statements: 11
11: Highly Flammable
Safety Statements: 9-16-29-33
9: Keep container in a well-ventilated place
16: Keep away from sources of ignition - No smoking
29: Do not empty into drains
33: Take precautionary measures against static discharges
RIDADR: UN 1325 4.1/PG 2
WGK Germany: 1
RTECS: RB7900000
HazardClass: 4.1
PackingGroup: II
F 13
Mildly toxic by ingestion. When heated to decomposition it emits acrid smoke and irritating fumes.
Norbornylene (498-66-8) is stench white mass, known as Bicyclo(2.2.1)heptene ; 3,6-Endomethylenecyclohexene ; NSC 120425 ; Norbornene ; Norbornylene ; Norcamphene ; Norfenchene ; 8,9,10-Trinorborn-2-ene ; Bicyclo(2.2.1)hept-2-ene . It is incompatible with strong oxidizing agents. When heated to decomposition, it yields Carbon monoxide , Carbon dioxide .
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