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
• Canonical 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).

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.