exo-5-Norbornene-2-methanol

• CAS: 13360-81-1
• Catalog Number: ACM13360811-1
• Category: Main Products
• Molecular Weight: 124.18g/mol
• Molecular Formula: C8H12O
• Synonyms: exo-5-Norbornenyl methyl alcohol
• IUPAC Name: 2-bicyclo[2.2.1]hept-5-enylmethanol
• SMILES: C1C2CC(C1C=C2)CO
• InChI: InChI=1S/C8H12O/c9-5-8-4-6-1-2-7(8)3-6/h1-2,6-9H,3-5H2
• InChI Key: LUMNWCHHXDUKFI-UHFFFAOYSA-N
• Complexity: 140
• Covalently-Bonded Unit Count: 1
• EC Number: 202-392-0
• Exact Mass: 124.088815g/mol
• Formal Charge: 0
• H-Bond Acceptor: 1
• H-Bond Donor: 1
• Heavy Atom Count: 9
• Monoisotopic Mass: 124.088815g/mol
• NSC Number: 403110
• Rotatable Bond Count: 1
• XLogP3: 1.2

Case Study

Exo-5-Norbornene-2-Methanol for the Synthesis of Norbornene Thiolactone Derivatives

Frank, Daniel, et al. European Polymer Journal, 2018, 98, 246-253.

To combine the elasticity of norbornene and the modifiability of thiolactone, two norbornene thiolactone derivatives were synthesized in this work. The monomer (M1) was derived from exo-5-norbornene-2-methanol and was used in amine-thiol-ene (ATE) and free radical polymerization (FRP) experiments. For comparative experiments of ROMP and amine-thiol-ene polymerization, M1 based on an endo/exo mixture of 5-norbornene-2-methanol was used.
Synthesis of M1 from exo-5-norbornene-2-methanol
· Exo-M1. Before its use, exo-5-norbornene-2-methanol was dried under high vacuum for 4 hours. A total of 4.04 g of exo-norbornene methanol (34.6 mmol, 1.0 eq.) was then dissolved in 10 mL of dry ethyl acetate within a Schlenk flask fitted with a septum and stir bar. Thiolactone isocyanate (5.00 g, 35.5 mmol, 1.02 eq.) and 50 µL of dibutyltin dilaurate (DBTL) were introduced via cannula, and the resulting mixture was stirred at room temperature. After one hour, the temperature was increased to 60 °C. Once the reaction was complete, the mixture was allowed to cool to room temperature, and the crude product was purified through column chromatography using a hexane/ethyl acetate 1:1 solvent system. This process yielded 88% of a colorless oil, which crystallized overnight.
· (Endo/exo)-M1. The same method was employed to synthesize a mixture of (endo/exo) M1, resulting in another colorless liquid that solidified overnight, with a yield of 90.4%.

Exo-5-Norbornene-2-Methanol for the Preparation of Norbornene-Based Copolymers and Their LED Applications

Kimyonok, Alpay, et al. Chemistry of Materials, 2007, 19(23), 5602-5608.

The synthesis of random copolymers containing 2,7-di-(carbazol-9-yl)fluorene-type host moieties and various iridium complexes in the side chains was developed. These copolymers emit light in various regions of the visible spectrum, and they were successfully used to prepare iridium poly(norbornene)-based OLED devices.
Syntheses of iridium complex containing monomers
· Compound 1 was synthesized by exploiting the most acidic hydrogen in the benzene ring of ppf through its reaction with BuLi, followed by treatment with CO2. Coupling of 1 to exo-5-norbornene-2-methanol yielded 2, which was metalated to yield the Ir(ppf)3-based monomer 3. The synthesis of complex 6 involved reacting the iridium dimer (Ir(btpy)2Cl)2 with 4-(2-pyridine)benzaldehyde. The aldehyde group in compound 6 was subsequently reduced to an alcohol using LiAlH4, yielding compound 9, which was esterified with exo-5-norbornene-2-carboxylic acid to form monomer 12.
· The synthesis procedure for compound 2 is as follows: Compound 1 (2.7 g, 11.5 mmol), exo-5-norbornene-2-methanol (1.4 g, 11.5 mmol), and dimethylaminopyridine (0.3 g, 2.45 mmol) were mixed in 100 mL of THF. A solution of dicyclohexylcarbodiimide (2.7 g, 13.1 mmol) in 10 mL of THF was introduced, and the mixture was stirred under argon at room temperature for 24 hours. After evaporation of the solvent and purification by column chromatography, compound 2 was obtained as a transparent oil (2.6 g, 66% yield).

Precise block copolymer synthesis using exo-5-norbornene-2-methanol

Ji, Eunkyung, Cian Cummins, and Guillaume Fleury. Molecules 26.5 (2021): 1412.

Bottlebrush block copolymers (BBCPs) can self-assemble into ordered, macroperiodic structures, significantly expanding the application range of photonic and membrane technologies. A two-step synthesis and rapid thin film self-assembly of poly(l-lactide)-b-polystyrene (PLLA- b -PS) BBCP was demonstrated. Using exo-5-norbornene-2-methanol as a starting material, PLLA chains were grown via ring-opening polymerization (ROP) of l-lactide to produce norbornene-terminated PLLA. Norbornene-terminated PS was prepared by anionic polymerization and then terminated with exo-5-norbornene-2-carbonyl chloride. PLLA- b -PS BBCP was prepared from two norbornene-based macromonomers via a one-pot sequential ring-opening metathesis polymerization (ROMP). PLLA- b -PS BBCPs films exhibited cylindrical and lamellar morphologies, depending on the relative block volume fraction, with domain sizes ranging from 46-58 nm and periods of 70-102 nm. Furthermore, a nanoporous template was fabricated by selectively etching the PLLA blocks within the ordered structure.
ε-Lactide and exo-5-norbornene-2-methanol were added to a flame-dried flask connected to a flask containing toluene. After evacuating and backfilling the flask with argon three times, 40 mL of toluene was added to dissolve the monomers. The flask was then placed in an oil bath heated to 60°C, and stannous octoate was added via syringe to initiate polymerization. After 18 hours, the resulting solution was cooled to room temperature, and an aliquot was collected for conversion analysis using 1H NMR before precipitation into cold methanol. The resulting polymer was filtered, washed with methanol, and dried overnight in a vacuum oven.

Synthesis of a cationic bottlebrush homopolymer using exo-5-norbornene-2-methanol

Senkum, Hathaithep, and William M. Gramlich. Macromolecular Chemistry and Physics 221.5 (2020): 1900476.

A cationic bottlebrush homopolymer was prepared using a graft-through method, starting with exo-5-norbornene-2-methanol and then via ring-opening metathesis polymerization, resulting in a well-defined polymer. A tertiary amine macromonomer synthesized via reversible addition-fragmentation chain transfer polymerization was then quaternized to produce a quaternary ammonium macromonomer. The quaternary ammonium macromonomer was subjected to a ROMP reaction to achieve the target molecular weight and low dispersity.
Synthesis of NB-RAFT CTA: A coupling reaction between exo-5-norbornene-2-methanol and DDMAT CTA was performed using DCC and DMAP in DCM. In a 100 mL round-bottom flask, exo-5-norbornene-2-methanol, DDMAT CTA, and DMAP were dissolved in 40 mL of anhydrous DCM. DCC was added to the solution, resulting in a cloudy mixture, which was stirred for 15 hours. The solid was filtered off under vacuum, and the yellow liquid filtrate was concentrated by rotary evaporation and purified by column chromatography using a 75:25 DCM:hexane mixture as solvent to obtain a yellow liquid NB-RAFT CTA.

Custom Q&A

What is the molecular formula of exo-5-Norbornene-2-methanol?

The molecular formula is C8H12O.

What are the synonyms for exo-5-Norbornene-2-methanol?

The synonyms are 5-Norbornene-2-methanol, Bicyclo[2.2.1]hept-5-en-2-ylmethanol, Bicyclo[2.2.1]hept-5-ene-2-methanol, and Cyclol.

What is the molecular weight of exo-5-Norbornene-2-methanol?

The molecular weight is 124.18 g/mol.

When was exo-5-Norbornene-2-methanol created?

It was created on March 26, 2005.

What is the IUPAC name of exo-5-Norbornene-2-methanol?

The IUPAC name is 2-bicyclo[2.2.1]hept-5-enylmethanol.

What is the InChI of exo-5-Norbornene-2-methanol?

The InChI is: InChI=1S/C8H12O/c9-5-8-4-6-1-2-7(8)3-6/h1-2,6-9H,3-5H2.

What is the InChIKey of exo-5-Norbornene-2-methanol?

The InChIKey is LUMNWCHHXDUKFI-UHFFFAOYSA-N.

What is the Canonical SMILES of exo-5-Norbornene-2-methanol?

The Canonical SMILES is C1C2CC(C1C=C2)CO.

What is the CAS number of exo-5-Norbornene-2-methanol?

The CAS number is 95-12-5.

What is the topological polar surface area of exo-5-Norbornene-2-methanol?

The topological polar surface area is 20.2Ų.