5-ACETYL-2-NORBORNENE

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5-ACETYL-2-NORBORNENE Basic information
Product Name:5-ACETYL-2-NORBORNENE
Synonyms:2-ACETYL-5-NORBORNENE;1-BICYCLO[2.2.1]HEPT-5-EN-2-YL-ETHANONE;5-NORBORNENE-2-ACETYL;ACETYLNORBORNENE;5-ACETYL-2-NORBORNENE;5-ACETYLBICYCLO[2.2.1]HEPT-2-ENE;Bicyclo[2.2.1]hept-2-ene, 5-acetyl-;Bicyclo[2.2.1]hept-5-ene, 2-acetyl-
CAS:5063-03-6
MF:C9H12O
MW:136.19
EINECS:225-767-0
Product Categories:Norbornene Derivatives
Mol File:5063-03-6.mol
5-ACETYL-2-NORBORNENE Structure
5-ACETYL-2-NORBORNENE Chemical Properties
Boiling point 84-86 °C18 mm Hg(lit.)
density 1.005 g/mL at 25 °C(lit.)
vapor pressure 45.33Pa at 25℃
refractive index n20/D 1.484(lit.)
Fp 143 °F
storage temp. 4°C
solubility Chloroform, Methanol (Slightly)
form Liquid
Specific Gravity1.005
color Clear light yellow to yellow-brown
InChI1S/C9H12O/c1-6(10)9-5-7-2-3-8(9)4-7/h2-3,7-9H,4-5H2,1H3/t7-,8+,9/m1/s1
InChIKeyNIMLCWCLVJRPFY-WGTSGOJVSA-N
SMILESCC(=O)C1C[C@H]2C[C@@H]1C=C2
LogP2.05
CAS DataBase Reference5063-03-6(CAS DataBase Reference)
Safety Information
Hazard Codes Xn
Risk Statements 22
Safety Statements 24/25-37-26
RIDADR 1993
WGK Germany 3
HazardClass 3.2
PackingGroup III
HS Code 29142990
Storage Class10 - Combustible liquids
Hazard ClassificationsAcute Tox. 4 Oral
MSDS Information
ProviderLanguage
SigmaAldrich English
ACROS English
5-ACETYL-2-NORBORNENE Usage And Synthesis
Chemical Propertiesclear light yellow to yellowish-brown liquid
Uses2-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.
Uses5-Acetyl-2-norbornene is an intermediate used in the synthesis of the 2-acetylnorbornyl isothiocyanates.
General Description2-Acetyl-5-norbornene, mixture of endo and exo is a colorless to light yellow liquid.
Synthesis
endo-2-Acetylbicyclo[2.2.1]hept-5-ene

824-60-2

endo-2-Acetylbicyclo[2.2.1]hept-5-ene

824-60-2

The general procedure for synthesizing endo-5-acetyl-2-norbornene from endo-5-acetyl-2-norbornene was as follows: in a sealed vessel equipped with a 15 mL stir bar, 6.81 g (50 mmol) of 2-acetyl-5-norbornene (containing 18.7% of the exoform and 79.7% of the endoform isomer, and the ratio of the exoform to the endoform isomer was 0.23) as component (A), followed by the addition of 0.21 g (2.5 mmol) of N-methylpyrrolidine. The vessel was sealed under nitrogen protection and the reaction mixture was placed in a thermostatic bath and the reaction was stirred sequentially at 100 °C, 120 °C and 140 °C for 2 h each to promote the differential isomerization reaction. The reaction process was monitored by gas chromatography (GC) and the results of GC analysis were recorded in Table 6.

References[1] Patent: JP2015/3879, 2015, A. Location in patent: Paragraph 0039-0041
5-ACETYL-2-NORBORNENE Preparation Products And Raw materials
Raw materialsendo-2-Acetylbicyclo[2.2.1]hept-5-ene
Tag:5-ACETYL-2-NORBORNENE(5063-03-6) Related Product Information
Norbornene EXO-NORBORNEOL endo-2-Acetyl-5-norbornene exo-5-Acetyl-2-norbornene 4-METHYL-5-OXATETRACYCLO[7.2.1.0(2,8).0(4,6)]DODEC-10-ENE-3,7-DIONE 5-OXATETRACYCLO[7.2.1.0(2,8).0(4,6)]DODEC-10-ENE-3,7-DIONE 2-BENZOYL-5-NORBORNENE 12-(1-METHYLETHYLIDENE)-5-OXATETRACYCLO[7.2.1.0(2,8).0(4,6)]DODEC-10-ENE-3,7-DIONE 1,4,4 A,8 A-TETRAHYDRO-ENDO-1,4-METHANONAPHTHALENE-5,8-DIONE 5-ACETYL-2-NORBORNENE CYCLOPENTADIENE-QUINONE (2:1)ADDUCT