6143-29-9

Basic information

• Product Name: 5-NORBORNEN-2-YL ACETATE
• Synonyms: 2-acetoxy-5-norbornene;5-Norbornen-2-yl acetate, mixture of endo and exo;Acetic acid, 5-norbornen-2-yl ester;Acetic acid, bicyclo[2.2.1]hept-5-en-2-yl ester;Bicyclo[2.2.1]hept-5-en-2-ol, acetate;5-NORBORNENE-2-YL ACETATE;5-NORBORNEN-2-YL ACETATE;BICYCLO[2.2.1]-5-HEPTEN-2-YL ACETATE
• CAS NO: 6143-29-9
• Molecular Formula: C9H12O2
• Molecular Weight: 152.19
• EINECS: 228-144-1
• Product Categories: C8 to C9;Carbonyl Compounds;Esters;Norbornene Derivatives;Halogenated Heterocycles ,Thiophenes ,Thiazolines/Thiazolidines
• Mol File: 6143-29-9.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 73-76 °C14 mm Hg(lit.)
• Flash Point: 144 °F
• Appearance: clear colorless to faintly yellow liquid
• Density: 1.044 g/mL at 25 °C(lit.)
• Vapor Pressure: 5.8E-12mmHg at 25°C
• Refractive Index: n20/D 1.47(lit.)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 5-NORBORNEN-2-YL ACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-NORBORNEN-2-YL ACETATE(6143-29-9)
• EPA Substance Registry System: 5-NORBORNEN-2-YL ACETATE(6143-29-9)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 6143-29-9(Hazardous Substances Data)

Usage

Description

5-NORBORNEN-2-YL ACETATE is a clear, colorless to faintly yellow liquid that is a derivative of norbornene. It is a compound with unique chemical properties that make it suitable for various applications in different industries.

Uses

Used in Chemical Research and Development:
5-NORBORNEN-2-YL ACETATE is used as a research compound for studying the ring-opening metathesis polymerization (ROMP) of norbornene. This process is catalyzed by dinuclear complex Cp2Os2Br4 (Cp = pentamethylcyclopentadienyl) and related compounds. The study of ROMP is essential for understanding the behavior of norbornene derivatives and their potential applications in various fields.
Used in Polymer Industry:
5-NORBORNEN-2-YL ACETATE is used as a monomer in the polymer industry for the synthesis of various polymers through the ring-opening metathesis polymerization process. These polymers have potential applications in coatings, adhesives, and other materials due to their unique properties.
Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, 5-NORBORNEN-2-YL ACETATE could potentially be used in the pharmaceutical industry as an intermediate in the synthesis of various drugs or drug candidates. Its unique chemical structure may offer new opportunities for drug development.
Used in Material Science:
5-NORBORNEN-2-YL ACETATE may also be used in material science for the development of new materials with specific properties. The ring-opening metathesis polymerization process allows for the creation of polymers with tailored characteristics, which could be useful in various applications such as automotive, aerospace, or electronics industries.

Biochem/physiol Actions

5-Norbornen-2-yl acetate undergoes copolymerisation with ethylene by nickel catalyst system to form high molecular weight functionalized polyethylene bearing ester functionalities. -Norbornen-2-yl acetate is the starting reagent for synthesis of urea condensation products from a-dicarbonyl compounds using Bi (OTf)3 catalyst.

InChI:InChI=1/C23H23NO4/c25-22(23-12-15-9-16(13-23)11-17(10-15)14-23)8-6-18-5-7-21(28-18)19-3-1-2-4-20(19)24(26)27/h1-8,15-17H,9-14H2/b8-6+

Upstream product

• 279-19-6 nortricyclane 
• 64-19-7 acetic acid 
• 108-05-4 vinyl acetate 
• 542-92-7 cyclopenta-1,3-diene 
• 72150-05-1 Essigsaeure<6endo-tosyloxy-2endo-norbornyl>ester 
• 72150-05-1 Essigsaeure-<6exo-tosyloxy-2endo-norbornyl>ester 
• 694-98-4 norborn-5-en-2-one 

Downstream Products

• 29583-33-3 (+/-)-endo-norborneol acetate 
• 34640-76-1 exo-2-norbornyl acetate 
• 162307-06-4 5-exo,6-exo-difluorobicyclo<2.2.1>heptan-2-yl acetate 
• 694-97-3 (1S,2S,4S)-bicyclo[2.2.1]hept-5-en-2-ol 
• 106928-44-3 (1R,2R,4R)-endo-bicyclo[2.2.1]hept-5-en-2-ol 
• 154278-40-7 (1S,2S,4S)-bicyclo[2.2.1]hept-5-en-2-yl acetate 
• 75305-52-1 Essigsaeure-<6exo-hydroxy-2endo-norbornyl>ester 
• 615249-15-5 Essigsaeure-<5exo-hydroxy-2endo-norbornyl>ester 
• 75305-52-1 Essigsaeur-<6endo-hydroxy-2endo-norbornyl>ester 
• 112836-09-6 (1R,2R,4R)-bicyclo[2.2.1]hept-5-en-2-yl acetate 
• 737805-27-5 (5-exo,6-exo)-5,6-dibenzoyloxybicyclo[2.2.1]heptane-2,3-dione 

Relevant articles and documents

(Meth) acrylate derivative, polymer and photoresist composition having lactone structure, and method for forming pattern by using it

There are here disclosed a photoresist material for lithography using a light of 220 nm or less which comprises at least a polymer represented by the following formula (2) and a photo-acid generator for generating an acid by exposure: wherein R1, R2, R3 and R5 are each a hydrogen atom or a methyl group; R4 is an acid-labile group, an alicyclic hydrocarbon group having 7 to 13 carbon atoms, which has an acid labile group, an alicyclic hydrocarbon group having 7 to 13 carbon atoms, which has a carboxyl group, or a hydrocarbon group having 3 to 13 carbon atoms, which has an epoxy group; R6 is a hydrogen atom, a hydrocarbon group having 1 to 12 carbon atoms, or an alicyclic hydrocarbon group having 7 to 13 carbon atoms, which has a carboxyl group; x, y and z are optional values which meet x+y+z=1, 0a weight-average molecular weight of the polymer is in the range of 2000 to 200000, and a resin having a (meth)acrylate unit of an alicyclic lactone structure represented by the formula (3): wherein R8 is a hydrogen atom or a methyl group, and R9 is a hydrocarbon group of 7 to 16 carbon atoms having an alicyclic lactone structure.

Ring-opening metathesis - Cross-metathesis reactions (ROM-CM) of substituted norbornadienes and norbornenes

Ring-opening metathesis - cross-metathesis reactions (ROM-CM) of substituted norbornadienes and norbornenes were investigated. The reactions with symmetrical 2,3-disubstituted norbornadienes were found to be highly chemoselective, with the ROM reactions occurring only on the less substituted or less sterically hindered double bonds regardless of the electronic nature of the substituents, giving highly substituted cyclopentenes in moderate to good yields. This study provides an efficient method for the stereoselective synthesis of highly substituted cyclopentenoids. Long-range electronic effect of a remote substituent on unsymmetrical norbornenes in the ROM-CM reactions was also investigated. Low levels of regioselectivities were observed (50:50 to 69:31) with various remote substituents on the norbornenes.

Remote substituent effects on the oxymercuration of 2-substituted norbornenes: An experimental and theoretical study

The effect of a remote substituent on regioselectivity in the oxymercuration of 2-substituted norbornenes has been investigated experimentally and theoretically using density functional theory (DFT). Regioselectivities of 1:1 to 14:1 were observed with various 2-substituted norbornenes. Exo-2-substituted norbornenes always gave greater regioselectivities compared to the corresponding endo-2-substituted norbornenes. The effects of solvents on the regioselectivity have also been examined, and ethereal solvents were found to be the best choice giving the optimal yield and regioselectivity. The relative rate of oxymercuration was estimated by competition experiments. The least reactive substrate (X = OAc) gave the highest regioselectivity. According to DFT predictions, the increased difference between the reaction barriers that results in the greater regioselectivity is correlated directly with the larger polarity of the C=C double bond, which is attacked by the mercury and oxygen. A number of stable exo and endo conformers were predicted. All exo conformers show the same polarity of the double bond, while some endo conformers have a reversal of this polarity. All the conformers except those with the OAc substituent are very close in energy and thus should react. The existence of a mixture of endo conformers with the C=C double bond of opposite polarity clearly explains a decrease in regioselectivity for the endo species. The origin of the greatest regioselectivity for the OAc-2-norbornenes lies in the fact that the conformer with the largest polarity is notably lower in energy than others due to an internal C-H-O hydrogen bond.