2-Acetyl-5-norbornene

Base Information

• Chemical Name: 2-Acetyl-5-norbornene
• CAS No.: 5063-03-6
• Molecular Formula: C9H12O
• Molecular Weight: 136.194
• Hs Code.: 29142990
• European Community (EC) Number: 225-767-0
• DSSTox Substance ID: DTXSID50964865
• Nikkaji Number: J21.539B
• Mol file: 5063-03-6.mol

Synonyms:5063-03-6;2-Acetyl-5-norbornene;5-Acetyl-2-norbornene;1-(Bicyclo[2.2.1]hept-5-en-2-yl)ethanone;Methyl 5-norbornen-2-yl ketone;5-Acetylbicyclo[2.2.1]hept-2-ene;1-{bicyclo[2.2.1]hept-5-en-2-yl}ethan-1-one;Ethanone, 1-bicyclo[2.2.1]hept-5-en-2-yl-;1-(2-bicyclo[2.2.1]hept-5-enyl)ethanone;exo-2-Acetylbicyclo[2.2.1]hept-5-ene;endo-2-Acetylbicyclo[2.2.1]hept-5-ene;824-61-3;MFCD00167570;1-(5-bicyclo[2.2.1]hept-2-enyl)ethanone;5-acetylnorbornene;Methyl (8,9,10-trinorborn-5-en-2-yl) ketone;SCHEMBL301403;NIMLCWCLVJRPFY-UHFFFAOYSA-;DTXSID50964865;AMY32005;EINECS 225-767-0;STL363939;AKOS000121432;AKOS016347360;AKOS025243982;AC-4859;AS-49964;Bicyclo[2.2.1]hept-2-ene, 5-acetyl-;Bicyclo[2.2.1]hept-5-ene, 2-acetyl-;SY015353;1-Bicyclo[2.2.1]hept-5-en-2-ylethanone;1-(6-bicyclo[2.2.1]hept-2-enyl)ethanone;A1045;FT-0619931;1-Bicyclo[2.2.1]hept-5-en-2-ylethanone #;EN300-21212;O10317;Ethanone, 1-[bicyclo[2.2.1]hept-5-en-2-yl]-;J-650008;J-650394;F0001-1321;Z104494380

Chemical Property of 2-Acetyl-5-norbornene

Chemical Property:

• Appearance/Colour: clear light yellow to yellowish-brown liquid
• Vapor Pressure: 0.514mmHg at 25°C
• Refractive Index: n20/D 1.484(lit.)
• Boiling Point: 191.5 °C at 760 mmHg
• Flash Point: 61.7 °C
• PSA: 17.07000
• Density: 1.049 g/cm³
• LogP: 1.78760
• Storage Temp.: 4°C
• Solubility.: Chloroform, Methanol (Slightly)
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 136.088815002
• Heavy Atom Count: 10
• Complexity: 193

Purity/Quality:

98%,99%, ^*data from raw suppliers

5-Acetyl-2-norbornene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 24/25-37-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)C1CC2CC1C=C2
• Uses: 2-Acetyl-5-norbornene was used in the synthesis of the 2-acetylnorbornyl isothiocyanates: exo-2-acetyl-exo-6-isothiocyanatonorbornane, endo-2-acetyl-exo-6-isothiocyanatonorbornane and exo-2-acetyl-exo-5-isothiocyanatonorbornane. 5-Acetyl-2-norbornene is an intermediate used in the synthesis of the 2-acetylnorbornyl isothiocyanates.

Technology Process of 2-Acetyl-5-norbornene

There total 36 articles about 2-Acetyl-5-norbornene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

N-methoxy-methylbicyclo[2.2.1]hept-5-ene-2-carboxamide + methyllithium (917-54-4) → 2-acetyl-5-norbornene (5063-03-6)

Guidance literature:

In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1021/ol0257981

Reference yield: 99.0%

N-hydroxy-N-methylbicyclo[2.2.1]hept-5-ene-2-carboxamide + methyllithium (917-54-4) → 2-acetyl-5-norbornene (5063-03-6)

Guidance literature:

In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1021/ol025799t

Reference yield: 95.06%

cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) + methyl vinyl ketone (78-94-4,25038-87-3) → 2-acetyl-5-norbornene (824-60-2) + exo-5-acetyl-2-norbornene (824-60-2,824-61-3,5063-03-6,58001-95-9,65166-67-8,107740-92-1,128441-68-9)

Guidance literature:

With [O=P(2-py)3W(CO)(NO)2](BF₄)2; In nitromethane; at 20 ℃; for 5h;

DOI:10.1016/j.tet.2004.09.078

upstream raw materials:

4-chloro-2-butanone

ethanol

potassium acetate

cyclopenta-1,3-diene

Downstream raw materials:

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

5-Acetyl-2,3-epoxybicyclo<2.2.1>heptane

exo-5-acetyl-2-norbornene

3-diethylamino-1-norborn-5-en-2-yl-1-phenyl-propan-1-ol

Refernces

• 1、 Rideout, Darryl C.,Breslow, Ronald. "Hydrophobic Acceleration of Diels-Alder Reactions". . p. 7816 - 7817. Retrieved 1980.
• 2、 Wittkopp, Alexander,Schreiner, Peter R.. "Metal-free, noncovalent catalysis of Diels - Alder reactions by Neutral hydrogen bond donors in organic solvents and in water". . p. 407 - 414. Retrieved 2003.
• 3、 Imachi, Shouhei,Onaka, Makoto. "Entrapment of cyclopentadiene in zeolite NaY and its application for solvent-free Diels-Alder reactions in the nanosized confined environment". . p. 4943 - 4946. Retrieved 2004.
• 4、 Fujita, Ken-ichi,Muraki, Takahito,Hattori, Hatsuhiko,Sakakura, Toshiyasu. "Diels-Alder reaction using a dendritic copper(II) triflate-catalyst: a positive dendritic effect on the chemical yield". . p. 4831 - 4834. Retrieved 2006.
• 5、 Boelke, Andreas,Kuczmera, Thomas J.,Lork, Enno,Nachtsheim, Boris J.. "N-Heterocyclic Iod(az)olium Salts – Potent Halogen-Bond Donors in Organocatalysis". supporting information. p. 13128 - 13134. Retrieved 2021/08/09.
• 6、 Voelkel, Martin H. H.,Wonner, Patrick,Huber, Stefan Matthias. "Preorganization: A Powerful Tool in Intermolecular Halogen Bonding in Solution". . p. 214 - 224. Retrieved 2020/03/10.