17016-12-5

Usage

Uses

Used in Organic Synthesis:
5-(Bromomethyl)bicyclo[2.2.1]hept-2-ene is used as a reagent in organic synthesis for the modification of organic compounds. Its bromine atom enables various chemical reactions, contributing to the versatility and utility of 5-(BROMOMETHYL)BICYCLO[2.2.1]HEPT-2-ENE in creating a range of organic products.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 5-(Bromomethyl)bicyclo[2.2.1]hept-2-ene is used as a building block for the synthesis of potential drug molecules. Its unique structure and reactivity make it a promising candidate for the development of new therapeutic agents.
Used in Chemical Research:
5-(Bromomethyl)bicyclo[2.2.1]hept-2-ene is also utilized in chemical research to explore its reactivity and potential applications in various chemical processes. Its ability to undergo a wide range of chemical reactions makes it an interesting subject for scientific investigation and the development of new methodologies in organic chemistry.

Upstream product

• 77-73-6 bi(cyclopentadiene) 
• 106-95-6 allyl bromide 
• 542-92-7 cyclopenta-1,3-diene 
• 95-12-5 5-hydroxymethyl-2-norbornene 
• 50626-34-1 5-(Tosyloxymethyl)bicyclo<2.2.1>hept-2-ene 
• 77-73-6 endo-<2+4>-Dicyclopentadien 
• 42070-73-5 Toluene-4-sulfonic acid (1S,2R,4S)-1-bicyclo[2.2.1]hept-5-en-2-ylmethyl ester 
• 13360-81-1 5-norbornene-2-methanol 
• 769-85-7 methyl exo-5-norbornene-2-carboxylate 
• 71338-95-9 p-Toluolsulfonsaeure-<6exo-Bromomethyl-2exo-norbornyl>ester 
• 71338-95-9 6-endo-bromomethylene-2-exo-norbornyl tosylate 
• 2903-75-5 (1S,2S,4S)-Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester 
• 15507-06-9 5-norbornene-2-methanol 
• 21423-87-0 1,3-dicyclopentadiene 

Downstream Products

• 6239-87-8 Tricyclo<3.2.1.0^3.6>octan-2-one 
• 83988-54-9 2-(5-norbornen-endo-2-yl)ethyl p-toluenesulfonate 
• 1007-01-8 endo-2-bicyclo<2.2.1>heptylacetic acid 

Relevant academic research and scientific papers

High Tg sulfonated insertion polynorbornene ionomers prepared by catalytic insertion polymerization

A simple method to synthesize high Tg sulfonated ionomers based on catalytic insertion polynorbornene is reported. Copolymers of norbornene and 5-methyl alcohol norbornene (endo:exo = 82:18) or 5-methyl bromide norbornene (endo:exo = 86:14) as well as terpolymers of norbornene, 5-methyl alcohol norbornene and 5-hexyl norbornene are prepared using a cationic Pd catalyst. These copolymers are then thioacetylated. Using hydrogen peroxide as oxidant, a sulfonated polynorbornene is obtained. Ionomers containing as much as 30 mol% SO3H and with Tgs above 200 °C are obtained in a four-step procedure of overall 40-75% yield.

Disulfide monomers comprising ethylenically unsaturated norbornyl groups suitable for dental compositions

Dental compositions and disulfide monomers described. The disulfide monomer comprises a disulfide backbone group wherein each of the sulfur atoms are bonded to a group terminating with an ethylenically unsaturated norbornyl group; and at least one other monomer comprising at least two ethylenically unsaturated groups.

Grafting poly(ionic liquid) brushes for anti-bacterial and anti-biofouling applications

Polymer brushes provide an ideal platform for studying biofouling and screening anti-biofouling materials. In the present work, high-density poly(ionic liquid) brushes based on imidazolium salts were successfully grafted to surfaces via surface-initiated ring-opening metathesis polymerizations from catecholic initiator and their anti-microbial activity was evaluated. Very uniform poly(ionic liquid) coatings with thickness up to 80 nm were obtained on TiO2. Various characterization techniques including infrared spectroscopy, X-ray photoelectron spectroscopy, thermogravimetric analysis and transmission electron microscopy were used to characterize poly(ionic liquid) brushes modified TiO2 nanomaterials. Subsequently, the anti-bacterial and anti-biofouling properties of poly(ionic liquid) brushes were evaluated. It was found that poly(ionic liquid) brushes can obviously resist adhesion of Chlorella spores and the counter-anions have a key impact on the anti-microbial property. The hexafluorophosphate anion poly(ionic liquid) coated TiO 2 nanomaterials have excellent anti-bacterial properties compared to pristine TiO2 nanoparticles against both E. coli and S. aureus.

Stress relaxation via addition-fragmentation chain transfer in high T g, high conversion methacrylate-based systems

To reduce shrinkage stress which arises during the polymerization of cross-linked polymers, allyl sulfide functional groups were incorporated into methacrylate polymerizations to determine their effect on stress relaxation via addition-fragmentation chain transfer (AFCT). Additionally, stoichiometrically balanced thiol and allyl sulfide-containing norbornene monomers were incorporated into the methacrylate resin to maximize the overall functional group conversion and promote AFCT while also enhancing the polymer's mechanical properties. Shrinkage stress and reaction kinetics for each of the various functional groups were measured by tensometry and Fourier-transform infrared (FTIR) spectroscopy, respectively. The glass transition temperature (T g) and elastic moduli (E′) were measured using dynamic mechanical analysis. When the allyl sulfide functional group was incorporated into dimethacrylates, the polymerization-induced shrinkage stress was not relieved as compared with analogous propyl sulfide-containing resins. These analogous propyl sulfide-containing monomers are incapable of undergoing AFCT while having similar chemical structure and cross-link density to the allyl sulfide-containing methacrylates. Here, a monomethacrylate monomer that also contains a cyclic allyl sulfide (PAS) was found to increase the cross-linking density nearly 20 times as compared to an analogous monomethacrylate in which the allyl sulfide was replaced with an ethyl sulfide. Despite the much higher cross-link density, the PAS formulation exhibited no concomitant increase in stress. Thiol-norbornene resins were copolymerized in PAS to promote AFCT as well as to synergistically combine the ring-opening benefits associated with the thiol-ene reaction. AFCT resulted in a 63% reduction of polymerization stress and a 45 °C enhancement of the glass transition temperature in the allyl sulfide-containing thiol-norbornene-methacrylate system compared with rubbery dimethacrylates. When compared with conventional glassy dimethacrylates, this combined system has less than 10% of the typical shrinkage stress level while having similarly excellent mechanical properties.

Versatile route to functionalized vinylic addition polynorbornenes

Vinylic addition polynorbornenes bearing functional groups can be obtained in a versatile way by nucleophilic substitution of a halogen in new vinylic haloalkyl polynorbornenes. The latter are obtained by vinylic homo and copolymerization of norbornene and haloalkyl norbornenes catalyzed by [Ni(C 6F5)2(SbPh3)2]. This method circumvents the problem of catalyst deactivation encountered in classical copolymerizations with polar monomers. The content of substituted monomer in the copolymers is in the range 26-59%, depending on the monomer ratio in the feed. Nucleophilic substitution reactions afford polymers with ester, cyano, phenylthio, or azido groups in the same wide range of composition. Click chemistry on the azido polynorbornenes give polynorbornenes with pendant triazole groups.

Supported Chiral Mo-Based Complexes as Efficient Catalysts for Enantioselective Olefin Metathesis

Syntheses and catalytic activities of seven new polymer-supported chiral Mo-based complexes are disclosed. Four of the complexes are polystyrene-based, and three involve polynorbornene supports. Studies concerning the ability of the polymer-bound chiral c

Fishing for catalysts: Mechanism-based probes for active species in solution

A combination of derivatization with charged substrates and electrospray-ionization mass spectrometry is used to fish out the active species in a catalytic reaction. The observed species in the mass spectrometer corresponds to the resting state of the catalyst. Data for the ring-opening metathesis polymerization (ROMP) of norbornene by (Cy3P)2Cl2Ru=CHPh (Cy = cyclohexyl) are used to illustrate the method.

Synthesis of Organosilanes and Oligoorganosiloxanes by Hydrosilylation of Halomethyl Derivatives of Bicyclo[2.2.1]hept-5-ene

The reaction of halomethyl derivatives of bicyclo[2.2.1]hept-5-ene with dimethylphenylsilane and oligodimethylsiloxanes HSiMe2[OSiMe2]nH (n = 1-3) and CH3(CH2)3SiMe2[OSiMe 2]25H was investigated. Unlike hydrosilylation of allyl halides, the yields of the addition products in the studied system reach 85%.

Norbornene polymerization initiators and process for preparing same

The present invention relates to a novel compound, its use as an initiator in anionic polymerizations yielding norbornene-terminated homopolymers of block copolymers, and the further use of said norbornene-terminated polymers as macromonomers in the preparation of graft copolymers.

(ENDO)-5-(2-HALOETHYL)-2-NORBORNENE. A NEW RADICAL PROBE.

(endo)-5-(2-haloethyl)-2-norbornenes have been synthesized, and their corresponding radicals generated by reaction with sodium, magnesium, sodium naphthalenide and tri-n-butyltin hydride in the presence of AIBN to produce both straight chain and cyclized