2-Acetyl-5-norbornene supplier

Name
5-ACETYL-2-NORBORNENE
EINECS 225-767-0
CAS No. 5063-03-6
Article Data107
CAS DataBase
Density 1.049 g/cm³
Solubility
Melting Point
Formula C₉H₁₂O
Boiling Point 191.5 °C at 760 mmHg
Molecular Weight 136.194
Flash Point 61.7 °C
Transport Information 1993
Appearance clear light yellow to yellowish-brown liquid
Safety 24/25
Risk Codes 22
Molecular Structure
Hazard Symbols Xn
Synonyms Ketone,methyl 5-norbornen-2-yl (6CI,7CI,8CI);2-Acetyl-5-norbornene;2-Acetylbicyclo[2.2.1]hept-5-ene;5-Acetyl-2-norbornene;6-Acetylbicyclo[2.2.1]hept-2-ene;Methyl 5-norbornen-2-yl ketone;
PSA 17.07000
LogP 1.78760

Synthetic route

: N-methoxy-methylbicyclo[2.2.1]hept-5-ene-2-carboxamide

: 917-54-4
methyllithium

: 5063-03-6
2-acetyl-5-norbornene

Conditions

Conditions	Yield
In tetrahydrofuran at -78 - 20℃;	99%

: N-hydroxy-N-methylbicyclo[2.2.1]hept-5-ene-2-carboxamide

: 917-54-4
methyllithium

: 5063-03-6
2-acetyl-5-norbornene

Conditions

Conditions	Yield
In tetrahydrofuran at -78 - 20℃;	99%

: 542-92-7
cyclopenta-1,3-diene

: 78-94-4
methyl vinyl ketone

: 5063-03-6
2-acetyl-5-norbornene

Conditions

Conditions	Yield
With 1-ethyl-3-methyl-1H-imidazol-3-ium chloride at 20℃; for 0.166667h; Diels-Alder reaction;	89%
With 2,2'-bipyridine core dendrimer; copper(II) bis(trifluoromethanesulfonate) In dichloromethane at 20℃; Diels-Alder reaction;	88%
4,4'-dihydroxy-2,2'-bipyridine-based dendritic Cu complex In dichloromethane at 20℃; Diels-Alder reaction;	88%

: 6322-49-2
4-chloro-2-butanone

: 64-17-5
ethanol

: 127-08-2
potassium acetate

: 542-92-7
cyclopenta-1,3-diene

: 5063-03-6
2-acetyl-5-norbornene

...Expand

: 6322-49-2
4-chloro-2-butanone

: 542-92-7
cyclopenta-1,3-diene

: 5063-03-6
2-acetyl-5-norbornene

Conditions

Conditions	Yield
With ethanol; potassium acetate

: 13307-34-1
1-(Norborn-5-en-2-yl)-ethanol

: 5063-03-6
2-acetyl-5-norbornene

Conditions

Conditions	Yield
With tetrabutyl-ammonium chloride; dihydrogen peroxide; potassium carbonate; ammonium heptamolybdate In tetrahydrofuran for 144h; Ambient temperature; Yield given;

: 3048-64-4
5-vinyl-2-norbornene

: 5063-03-6
2-acetyl-5-norbornene

Conditions

Conditions	Yield
With tert.-butylhydroperoxide; silica-supported polyamidoamine dendrimer G1-C6-Pd(dba) In various solvent(s) at 55℃; for 24h;	22 % Chromat.

: 542-92-7
cyclopenta-1,3-diene

: 78-94-4
methyl vinyl ketone

A: 5063-03-6
2-acetyl-5-norbornene

B: 824-60-2, 824-61-3, 5063-03-6, 65166-67-8, 107740-92-1, 128441-68-9, 58001-95-9
bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester

C: 107740-92-1
endo-2-acetyl-bicyclo[2.2.1]hept-5-ene

Conditions

Conditions	Yield
With 2,6-dimethylpyridine; [Ru(η5-cyclopentadienyl)(BIPHOP-F)(acetone)][SbF6] In dichloromethane at -20℃; for 24h; Diels-Alder Cycloaddition; Molecular sieve; Schlenk technique; Inert atmosphere; Overall yield = 74 %; Overall yield = 66.2 mg;	A n/a B n/a C n/a

...Expand

: 542-92-7
cyclopenta-1,3-diene

: 78-94-4
methyl vinyl ketone

A: 5063-03-6
2-acetyl-5-norbornene

B: 159651-24-8
C9H12O

C: 159699-92-0
(2S)-1-bicyclo[2.2.1]hept-5-en-2-yl-ethanone

Conditions

Conditions	Yield
With [Ru(η5-C8H7)((S,S)-BIPHOP-F)(acetone)][SbF6]; lithium diisopropyl amide In dichloromethane at -20℃; for 48h; Diels-Alder Cycloaddition; Molecular sieve; Schlenk technique; Inert atmosphere; Overall yield = 76 %; Overall yield = 68.4 mg;	A n/a B n/a C n/a

...Expand

: 1604-29-1
1,1-dimethyl-2-propynyl acetate

: 5063-03-6
2-acetyl-5-norbornene

: Acetic acid 1-((1R,2R,3S,4S,5R,6S)-6-acetyl-tricyclo[3.2.1.02,4]oct-3-yl)-2-methyl-propenyl ester

Conditions

Conditions	Yield
chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium (II) In 1,4-dioxane at 20℃; for 17h;	98%

: 5063-03-6
2-acetyl-5-norbornene

: 58654-66-3
(+/-)-2-exo-norbornyl methyl ketone

Conditions

Conditions	Yield
With NaH-alkoxide-Ni salt-Me3SiCl reagent In tetrahydrofuran at 25℃; for 1h;	95%

: 5063-03-6
2-acetyl-5-norbornene

: 57-14-7
1,1-dimethylhydrazine

: N'-[1-Bicyclo[2.2.1]hept-5-en-2-yl-eth-(Z)-ylidene]-N,N-dimethyl-hydrazine

Conditions

Conditions	Yield
In diethyl ether for 3h;	75%

: 5063-03-6
2-acetyl-5-norbornene

: 593-56-6
N-methoxylamine hydrochloride

: 1-(bicyclo[2.2.1]hept-5-en-2-yl)ethan-1-one O-methyl oxime

Conditions

Conditions	Yield
With sodium acetate In methanol; water at 65℃; for 6.03333h;	75%

: 5063-03-6
2-acetyl-5-norbornene

Reaxys ID: 12353132: Reaxys ID: 12353132

Conditions

Conditions	Yield
benzylidenedichlorobis(1,3-diisopropylimidazolin-2-ylidene)ruthenium In 1,1-dichloroethane at 50℃; for 2h; Conversion of starting material;	67%
benzylidenedichlorobis(1,3-diisopropylimidazolin-2-ylidene)ruthenium In dichloromethane at 25℃; for 2h; Conversion of starting material;	42%

: 5063-03-6
2-acetyl-5-norbornene

: 10328-92-4
N-Methylisatoic anhydride

: 1450620-05-9
2-acetyl-10-methyl-1,3,4,4a,9a,10-hexahydro-1,4-methanoacridin-9(2H)-one

Conditions

Conditions	Yield
With dichlorobis(trimethylphosphine)nickel; zinc In toluene at 120℃; for 12h; Inert atmosphere;	55%

: 5063-03-6
2-acetyl-5-norbornene

: 18295-60-8
propargyl magnesium bromide

: 82415-79-0
2-(Bicyclo<2.2.1>hept-5-en-2-yl)-4-pentyn-2-ol

Conditions

Conditions	Yield
In diethyl ether for 6h; Heating;	46%

: 17284-97-8
3-Chloro-6-hydrazinopyridazine

: 5063-03-6
2-acetyl-5-norbornene

: 69579-30-2
1-(norborn-5-en-2-yl)-ethanone (6-chloro-pyridazin-3-yl)-hydrazone

Conditions

Conditions	Yield
toluene-4-sulfonic acid In benzene Heating;	30.5%

: 5063-03-6
2-acetyl-5-norbornene

: 141-78-6
ethyl acetate

: exo-5-acetoacetyl-2-norbornene

Conditions

Conditions	Yield
With sodium hydride In 1,2-dimethoxyethane for 16h; Heating;	30%

: 5063-03-6
2-acetyl-5-norbornene

: 333-20-0
potassium thioacyanate

: 1-((1S,2R,4S,5R)-5-Isothiocyanato-bicyclo[2.2.1]hept-2-yl)-ethanone

: (+/-)-exo-2-acetyl-6-isothiocyanatonorbornane

: 1-((1S,2R,4R,6R)-6-Isothiocyanato-bicyclo[2.2.1]hept-2-yl)-ethanone

Conditions

Conditions	Yield
With sulfuric acid In benzene at 50℃; for 96h;	A 23% B 22% C 10%

...Expand

: 50-00-0
formaldehyd

: 5063-03-6
2-acetyl-5-norbornene

: 660-68-4
diethyl amine hydrochloride

: 3-diethylamino-1-norborn-5-en-2-yl-propan-1-one

...Expand

: 50-00-0
formaldehyd

: 5063-03-6
2-acetyl-5-norbornene

: 10024-89-2
morpholin hydrochloride

: 3-morpholino-1-norborn-5-en-2-yl-propan-1-one

...Expand

: 5063-03-6
2-acetyl-5-norbornene

: 616-38-6
carbonic acid dimethyl ester

: 37734-07-9
methyl endo/exo-3-(bicyclo<2,2,1>hept-5-en-2-yl)-3-oxopropanoate

Conditions

Conditions	Yield
With sodium hydride In 1,2-dimethoxyethane

: 5063-03-6
2-acetyl-5-norbornene

: 100-52-7
benzaldehyde

: 73902-02-0
(E)-1-Bicyclo[2.2.1]hept-5-en-2-yl-3-phenyl-propenone

Conditions

Conditions	Yield
With methanesulfonyl chloride; triethylamine; lithium diisopropyl amide 1.) THF; Multistep reaction;

: 5063-03-6
2-acetyl-5-norbornene

: 75-07-0
acetaldehyde

: 69663-38-3, 70634-48-9, 70634-53-6
(E)-1-Bicyclo[2.2.1]hept-5-en-2-yl-but-2-en-1-one

Conditions

Conditions	Yield
With methanesulfonyl chloride; triethylamine; lithium diisopropyl amide 1.) THF; Multistep reaction;

: 5063-03-6
2-acetyl-5-norbornene

: 616-38-6
carbonic acid dimethyl ester

: 37734-07-9, 82738-06-5, 82738-07-6
methyl endo-3-(bicyclo<2,2,1>hept-5-en-2-yl)-3-oxopropanoate

: 37734-07-9, 82738-06-5, 82738-07-6
methyl exo-3-(bicyclo<2,2,1>hept-5-en-2-yl)-3-oxopropanoate

Conditions

Conditions	Yield
With sodium hydride 1.) THF, reflux, 2.) THF, reflux, 16 h; Multistep reaction. Title compound not separated from byproducts;

...Expand

: 5063-03-6
2-acetyl-5-norbornene

: 105-58-8
Diethyl carbonate

: 56342-58-6, 56342-68-8, 75275-66-0
ethyl endo-3-(bicyclo<2,2,1>hept-5-en-2-yl)-3-oxopropanoate

: 56342-58-6, 56342-68-8, 75275-66-0
ethyl exo-3-(bicyclo<2,2,1>hept-5-en-2-yl)-3-oxopropanoate

Conditions

Conditions	Yield
With sodium hydride 1.) THF, reflux, 2.) THF, reflux, 30 min; Multistep reaction. Title compound not separated from byproducts;

...Expand

: 5063-03-6
2-acetyl-5-norbornene

: 6203-08-3
methyl 5-norbornene-2-carboxylate

: 98511-29-6
1.3-Di--propan-1.3-dion

Conditions

Conditions	Yield
(i) NaH, DMSO, Cu(OAc)2*H2O, (ii) aq. H2SO4; Multistep reaction;

: 5063-03-6
2-acetyl-5-norbornene

A: 6-(1-Hydroxy-ethyl)-bicyclo[2.2.1]heptan-2-ol

B: 5-(1-Hydroxy-ethyl)-bicyclo[2.2.1]heptan-2-ol

C: 1-(6-Hydroxy-bicyclo[2.2.1]hept-2-yl)-ethanone

D: 1-(5-Hydroxy-bicyclo[2.2.1]hept-2-yl)-ethanone

Conditions

Conditions	Yield
With sodium perborate; bis(cyclohexanyl)borane 1.) THF; 2.) THF/water; Multistep reaction;

...Expand

: 5063-03-6
2-acetyl-5-norbornene

: 119-26-6
(2,4-dinitro-phenyl)-hydrazine

: N-(1-bicyclo[2.2.1]hept-5-en-2-yl-ethylidene)-N'-(2,4-dinitro-phenyl)-hydrazine

Conditions

Conditions	Yield
In ethanol at 20℃; for 0.5h;

: 5063-03-6
2-acetyl-5-norbornene

η3-allylpalladium(II) chloride dimer: η3-allylpalladium(II) chloride dimer

poly(5-acetyl-2-norbornene), terminated with allyl group: poly(5-acetyl-2-norbornene), terminated with allyl group

Conditions

Conditions	Yield
With Hexadecane; lithium tetrakis(pentafluorophenyl)borate ethyl etherate; sodium dodecyl-sulfate In water; toluene

2-Acetyl-5-norbornene Specification

The CAS register number of 2-Acetyl-5-norbornene is 5063-03-6. It also can be called as 6-Acetylbicyclo[2.2.1]hept-2-ene and the IUPAC name about this chemical is 1-(5-bicyclo[2.2.1]hept-2-enyl)ethanone. The molecular formula about this chemical is C₉H₁₂O and the molecular weight is 136.19. It belongs to the Norbornene Derivatives. This chemical is harmful if swallowed. When you are using it, please avoid contact with skin and eyes.

Physical properties about 2-Acetyl-5-norbornene are: (1)ACD/LogP: 1.45; (2)ACD/LogD (pH 5.5): 1.45; (3)ACD/LogD (pH 7.4): 1.45; (4)ACD/BCF (pH 5.5): 7.49; (5)ACD/BCF (pH 7.4): 7.49; (6)ACD/KOC (pH 5.5): 147.14; (7)ACD/KOC (pH 7.4): 147.14; (8)#H bond acceptors: 1; (9)#Freely Rotating Bonds: 1; (10)Polar Surface Area: 17.07Å²; (11)Index of Refraction: 1.515; (12)Molar Refractivity: 39.14 cm³; (13)Molar Volume: 129.7 cm³; (14)Polarizability: 15.51x10^-24cm³; (15)Surface Tension: 36.1 dyne/cm; (16)Enthalpy of Vaporization: 42.77 kJ/mol; (17)Boiling Point: 191.5 °C at 760 mmHg; (18)Vapour Pressure: 0.514 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(C1C[C@H]2/C=C\[C@@H]1C2)C
(2)InChI: InChI=1/C9H12O/c1-6(10)9-5-7-2-3-8(9)4-7/h2-3,7-9H,4-5H2,1H3/t7-,8+,9?/m0/s1
(3)InChIKey: NIMLCWCLVJRPFY-ZQTLJVIJBW
(4)Std. InChI: InChI=1S/C9H12O/c1-6(10)9-5-7-2-3-8(9)4-7/h2-3,7-9H,4-5H2,1H3/t7-,8+,9?/m0/s1
(5)Std. InChIKey: NIMLCWCLVJRPFY-ZQTLJVIJSA-N

Product Name

5-ACETYL-2-NORBORNENE

Synthetic route

2-Acetyl-5-norbornene Specification

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