4747-61-9

Basic information

• Product Name: 2-(6,6-dimethylbicyclo[3.1.1]hept-2-yl)ethanol
• Synonyms: 2-(6,6-dimethylbicyclo[3.1.1]hept-2-yl)ethanol;2-(6,6-Dimethylbicyclo[3.1.1]heptan-2-yl)ethanol;2-(6,6-dimethylnorpinan-2-yl)ethanol;2-(7,7-dimethyl-2-bicyclo[3.1.1]heptanyl)ethanol;Hydronopol;DIHYDRO NOPOL;2-(6,6-dimethyl-4-bicyclo[3.1.1]heptanyl)ethanol
• CAS NO: 4747-61-9
• Molecular Formula: C₁₁H₂₀O
• Molecular Weight: 168.2759
• EINECS: 225-267-2
• Mol File: 4747-61-9.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 234.5°Cat760mmHg
• Flash Point: 103.8°C
• Appearance: /
• Density: 0.941g/cm³
• Vapor Pressure: 0.0097mmHg at 25°C
• Refractive Index: 1.477
• PKA: 15.12±0.10(Predicted)
• CAS DataBase Reference: 2-(6,6-dimethylbicyclo[3.1.1]hept-2-yl)ethanol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(6,6-dimethylbicyclo[3.1.1]hept-2-yl)ethanol(4747-61-9)
• EPA Substance Registry System: 2-(6,6-dimethylbicyclo[3.1.1]hept-2-yl)ethanol(4747-61-9)

Safety Data

• Hazardous Substances Data: 4747-61-9(Hazardous Substances Data)

Usage

Uses

Used in Traditional Medicine:
2-(6,6-dimethylbicyclo[3.1.1]hept-2-yl)ethanol is used as a therapeutic agent in traditional medicine for its analgesic, anti-inflammatory, and sedative properties, helping to alleviate pain, reduce inflammation, and promote relaxation.
Used in Neurological Treatments:
In the field of neurology, 2-(6,6-dimethylbicyclo[3.1.1]hept-2-yl)ethanol is being investigated as a potential treatment for neurological disorders such as Alzheimer's disease and Parkinson's disease, due to its ability to cross the blood-brain barrier, which is crucial for the effective treatment of such conditions.
Used in the Food and Beverage Industry:
2-(6,6-dimethylbicyclo[3.1.1]hept-2-yl)ethanol is used as a flavoring agent in the food and beverage industry, adding unique taste profiles to various products, enhancing the sensory experience for consumers.
Used in Perfumes and Cosmetics:
In the perfumery and cosmetics industry, 2-(6,6-dimethylbicyclo[3.1.1]hept-2-yl)ethanol is used as a fragrance ingredient, contributing to the creation of complex and appealing scents in perfumes and other cosmetic products.
Used in Pharmaceutical Formulations:
2-(6,6-dimethylbicyclo[3.1.1]hept-2-yl)ethanol is also used in pharmaceutical formulations, where its ability to cross the blood-brain barrier can be leveraged for the development of drugs targeting the central nervous system.
Safety Considerations:
It is important to handle 2-(6,6-dimethylbicyclo[3.1.1]hept-2-yl)ethanol with caution, as it can be toxic in high doses and may cause irritation to the skin and respiratory system. Proper safety measures should be taken during its use in various applications to minimize potential adverse effects.

InChI:InChI=1/C11H20O/c1-11(2)9-4-3-8(5-6-12)10(11)7-9/h8-10,12H,3-7H2,1-2H3

Synthetic route

nopol (128-50-7) → dihydronopol (4747-61-9)

Conditions	Yield
With palladium on activated charcoal; hydrogen In ethanol at 20℃; Solvent; Reagent/catalyst;	88.9%
With hydrogen; nickel

1H-imidazole (288-32-4) + hydronopyl bromide (53207-03-7) → 1-[2-(6,6-dimethylbicyclo[3.1.1]heptan-2-yl)ethyl]imidazole + dihydronopol (4747-61-9)

Conditions	Yield
With potassium tert-butylate In hydrogenchloride; butan-1-ol

formaldehyd (50-00-0) + Beta-pinene (177698-19-0) → dihydronopol (4747-61-9)

Conditions	Yield
In benzonitrile at 90℃; for 10h; Catalytic behavior; Reagent/catalyst; Temperature; Solvent;

N-chloroacetylmorpholine (1440-61-5) + dihydronopol (4747-61-9) → C17H29NO3

Conditions	Yield
With sodium hydride In tetrahydrofuran at 0 - 20℃; Solvent; Reagent/catalyst;	88.2%

dihydronopol (4747-61-9) + N-(2-bromoethyl)-N-isopropylpropan-2-amine (90221-88-8) → 2-<2-Diisopropylamino-ethoxy>-ethyl-6,6-dimethyl-norpinan (38284-51-4)

Conditions	Yield
With sodium amide

dihydronopol (4747-61-9) → hydronopyl bromide (53207-03-7)

Conditions	Yield
With phosphorus tribromide

dihydronopol (4747-61-9) → 4-{2-[2-(6,6-dimethyl-norpinan-2-yl)-ethoxy]-ethyl}-morpholine (38284-47-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydride / tetrahydrofuran / 0 - 20 °C 2: sodium tetrahydroborate; boron trifluoride-tetrahydrofuran complex / tetrahydrofuran / 0 °C View Scheme

dihydronopol (4747-61-9) → Pinaverium bromide (53251-94-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydride / tetrahydrofuran / 0 - 20 °C 2: sodium tetrahydroborate; boron trifluoride-tetrahydrofuran complex / tetrahydrofuran / 0 °C 3: butanone / Reflux View Scheme

Upstream product

• 128-50-7 nopol 
• 288-32-4 1H-imidazole 
• 53207-03-7 hydronopyl bromide 
• 50-00-0 formaldehyd 
• 177698-19-0 Beta-pinene 

Downstream Products

• 53251-94-8 Pinaverium bromide 
• 38284-47-8 4-{2-[2-(6,6-dimethyl-norpinan-2-yl)-ethoxy]-ethyl}-morpholine 

Relevant articles and documents

Molybdenum oxide/γ-alumina: An efficient solid acid catalyst for the synthesis of nopol by Prins reaction

Prins condensation of β-pinene with paraformaldehyde was carried out over MoOx/γ-Al2O3 catalyst in liquid phase. MoOx/γ-Al2O3 catalysts with different loadings were synthesized by impregnation method and characterized by XRD, N2 sorption, NH3-TPD, UV-DRS, TEM and SEM. The surface area, TEM and UV-DRS measurements reveal complete coverage of alumina support by MoOx was achieved between 9 and 11 wt% loading in which the molybdenum is present as octahedral and tetrahedral species in the form of a monolayer domain and small clusters of MoOx. The effect of MoOx loading and calcination temperature of the catalysts on total acidity and catalytic activity in the Prins reaction were correlated. The total surface acid density of MoOx/γ-Al2O3 increased with an increase in MoOx loading until 11 wt% and further loading decreased the acidity. Among the different supports, ZrO2, TiO2, SiO2 and Nb2O5, γ-Al2O3 exhibited the best performance. The influence of solvent on the Prins reaction in terms of dielectric constant, acceptor and donor number was investigated. Solvents with both AN and DN in the range of 10 to 20 were suitable to facilitate the reaction. The effect of reaction temperature, catalyst amount, reactant mole ratio and reusability of the catalyst for the Prins reaction were investigated. The 11 wt% MoOx loaded on γ-Al2O3 showed the best performance with 96% β-pinene conversion with 86% nopol selectivity.

A synthesis method of pinaverium bromide

The invention relates to a pinaverium bromide synthesis method. Cheap and easily available morpholine as a raw material and an acylating agent undergo a reaction to produce a novel intermediate and pinaverium bromide is synthesized from the intermediate under mild conditions. Raw material reaction is complete, side reaction is less, the pinaverium bromide has treatment cis-isomeride content greater than or equal to 99% and trans-isomer content less than or equal to 1%, and product cis-isomer content is greatly improved.

Imidazole derivatives and salts thereof and pharmaceutical formulations useful in thrombo-embolic disorders

Imidazoles of formula (I) STR1 wherein A is a chemical bond or a straight or branched, saturated or unsaturated, aliphatic residue having from 1 to 6 carbon atoms wherein 1, 2 or 3 of such carbon atoms may be replaced by a corresponding number of heteroatoms selected from oxygen, sulphur and nitrogen providing (in the case of 2 or 3 heteroatoms) that any such heteroatom is not located adjacent to a further such heteroatoms or heteroatoms R is a fused, saturated or unsaturated, non-aromatic carbocyclic, polycyclic ring system; a saturated or unsaturated, carbocyclic spirocyclic ring system, optionally containing one or more ring heteroatoms selected from oxygen, sulphur and nitrogen; or a saturated or unsaturated, carbocyclic bridged-polycyclic ring system, optionally containing one or more ring heteroatoms selected from oxygen, sulphur and nitrogen and having one or more bridges; or AR together represent a straight or branched, saturated or unsaturated, aliphatic residue having 3 to 6 carbon atoms, wherein 1, 2 or 3 of such carbon atoms may be replaced by a corresponding number of heteroatoms selected from oxygen, sulphur and nitrogen providing (in the case of 2 or 3 heteroatoms) that any such heteroatom is not located adjacent to a further such heteroatom or heteroatoms; which aliphatic residue is substituted by at least two groups, which may be the same or different, selected from the groups specified for R above. and acid addition salts and pharmaceutically acceptable bioprecursors thereof. Methods of preparing the imidazoles are disclosed. The imidazoles and their acid addition salts and bioprecursors are useful in the treatment or prophylaxis of thrombo-embolic conditions.