Nopol

• CAS: 35836-73-8
• Catalog Number: ACM35836738
• Category: Main Products
• Molecular Weight: 166.26
• Molecular Formula: C₁₁H₁₈O
• Synonyms: AZD7687
• IUPAC Name: 2-[(1S,5R)-6,6-dimethyl-4-bicyclo[3.1.1]hept-3-enyl]ethanol
• Canonical SMILES: CC1(C2CC=C(C1C2)CCO)C
• InChI Key: ROKSAUSPJGWCSM-UWVGGRQHSA-N
• Boiling Point: 230ºC
• Flash Point: 98.9ºC
• Density: 0.978g/cm³
• Appearance: colorless viscous liquid
• EC Number: 252-744-2
• Exact Mass: 166.13600
• Hazard Statements: Xn: Harmful
• Safety Description: 26-37/39

Case Study

Synthesis of Nopol-Based Cationic Photopolymerizable Polysiloxane Oxacyclobutanes

Hu Y, et al. Progress in Organic Coatings, 2022, 163, 106681.

In this study, a series of bio-based cationic photopolymerizable polysiloxane oxacyclobutanes, derived from nopol with varying silicone chain lengths (Nopol-Sin, n = 3, 6, 9), were synthesized.
The synthesis procedure for Nopol-Sin is as follows:
First, a mixture of 9.6 g (240 mmol) NaH and paraffin wax (with NaH content at 60 wt%) was washed with 50 mL petroleum ether to remove the paraffin. The NaH was then added to a three-necked flask containing 150 mL anhydrous tetrahydrofuran (THF). Next, 200 mmol of nopol and 220 mmol of 3-ethyl-3-chloromethyloxybutane were introduced into the flask, and the mixture was stirred thoroughly before being heated to 50°C under reflux. After 6 hours of reaction, 50 mL of water was added to quench the reaction, and the solvent was removed using a rotary evaporator. The reaction mixture was then extracted three times with 100 mL ethyl acetate. The organic phase was washed three times with 50 mL water, followed by the addition of anhydrous magnesium sulfate, and the mixture was stirred overnight. Finally, the fraction collected at 140-150°C under reduced pressure via rotary evaporation yielded Intermediate 1.
Next, a three-necked flask equipped with a drop funnel, thermometer, and reflux condenser was purged with nitrogen three times. 20 mmol of Intermediate 1 and 40 mL of anhydrous toluene were added to the flask, followed by 1.32 g (for Si₃H), 2.32 g (for Si₆H), or 3.32 g (for Si₉H) of Karstedt catalyst (at a concentration of 100 ppm). After heating the mixture to 55°C, 20 mmol of hydrogen-containing methylsilicone oil was introduced into the reaction solution. The reaction proceeded at 90°C for 4 hours, completing the reaction. Finally, the solvent was removed under vacuum to obtain the desired Nopol-Sin product.

Custom Q&A

What is the molecular formula of Nopol?

The molecular formula of Nopol is C11H18O.

What is the IUPAC name of Nopol?

The IUPAC name of Nopol is 2-(6,6-dimethyl-2-bicyclo[3.1.1]hept-2-enyl)ethanol.

What is the InChI of Nopol?

The InChI of Nopol is InChI=1S/C11H18O/c1-11(2)9-4-3-8(5-6-12)10(11)7-9/h3,9-10,12H,4-7H2,1-2H3.

What is the InChIKey of Nopol?

The InChIKey of Nopol is ROKSAUSPJGWCSM-UHFFFAOYSA-N.

What is the canonical SMILES representation of Nopol?

The canonical SMILES representation of Nopol is CC1(C2CC=C(C1C2)CCO)C.

What is the CAS number of Nopol?

The CAS number of Nopol is 128-50-7.

What is the molecular weight of Nopol?

The molecular weight of Nopol is 166.26g/mol.

How many hydrogen bond donors are there in Nopol?

Nopol has 1 hydrogen bond donor.

How many hydrogen bond acceptors are there in Nopol?

Nopol has 1 hydrogen bond acceptor.

What is the topological polar surface area of Nopol?

The topological polar surface area of Nopol is 20.2Ų.