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6,6-Dimethyl-bicyclo[3.1.1]heptane-2-ethanol
[CAS# 4747-61-9]

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Identification
Classification Organic raw materials >> Alcohols, phenols, phenolic compounds and derivatives >> 2-Cycloalcohol
Name 6,6-Dimethyl-bicyclo[3.1.1]heptane-2-ethanol
Synonyms 2-(6,6-dimethyl-2-bicyclo[3.1.1]heptanyl)ethanol
Molecular Structure CAS # 4747-61-9, 6,6-Dimethyl-bicyclo[3.1.1]heptane-2-ethanol, 2-(6,6-dimethyl-2-bicyclo[3.1.1]heptanyl)ethanol
Molecular Formula C11H20O
Molecular Weight 168.28
CAS Registry Number 4747-61-9
EC Number 225-267-2
SMILES CC1(C2CCC(C1C2)CCO)C
Properties
Solubility 263.2 mg/L (25 ºC water)
Density 0.9±0.1 g/cm3, Calc.*
Index of Refraction 1.477, Calc.*
Melting point 39.12 ºC
Boiling Point 244.44 ºC, 234.5±8.0 ºC (760 mmHg), Calc.*
Flash Point 103.8±8.6 ºC, Calc.*
* Calculated using Advanced Chemistry Development (ACD/Labs) Software.
Safety Data
Hazard Symbols symbol symbol symbol   GHS05;GHS07;GHS09 Danger    Details
Hazard Statements H315-H318-H411    Details
Precautionary Statements P264-P264+P265-P273-P280-P302+P352-P305+P354+P338-P317-P321-P332+P317-P362+P364-P391-P501    Details
Hazard Classification
up    Details
HazardClassCategory CodeHazard Statement
Skin irritationSkin Irrit.2H315
Chronic hazardous to the aquatic environmentAquatic Chronic2H411
Serious eye damageEye Dam.1H318
up Discovory and Applicatios
6,6-Dimethyl-bicyclo[3.1.1]heptane-2-ethanol is a chemical compound characterized by a bicyclic structure, specifically the bicyclo[3.1.1]heptane skeleton, which is a fused ring system. The compound features a hydroxyl group (-OH) at the 2-position on the bicyclic ring, along with two methyl groups at the 6-position. This unique structure makes it an interesting molecule in both synthetic chemistry and various applications.

The compound was first synthesized as part of a broader effort to explore bicyclic compounds and their reactivity. Bicyclic systems, in general, are of significant interest in chemistry due to their structural rigidity and potential for creating compounds with unique chemical properties. The discovery and characterization of 6,6-dimethyl-bicyclo[3.1.1]heptane-2-ethanol expanded the understanding of how functional groups could be introduced to bicyclic systems and how they could be used in chemical synthesis.

One of the primary applications of 6,6-dimethyl-bicyclo[3.1.1]heptane-2-ethanol is in the field of organic synthesis. The compound can be used as a building block in the preparation of more complex molecules, particularly those that require the incorporation of a bicyclic structure. The presence of the hydroxyl group at the 2-position allows the compound to participate in a variety of reactions, such as esterification and nucleophilic substitution, making it a versatile intermediate for the synthesis of a wide range of chemicals.

The molecule is also valuable in the production of specialty chemicals, including those used in the fragrance and flavor industries. The bicyclic nature of 6,6-dimethyl-bicyclo[3.1.1]heptane-2-ethanol imparts a distinct odor profile, which has led to its use in the development of various aromatic compounds. Its specific structure gives rise to a unique combination of volatile components, making it suitable for use in perfumery and other applications where distinctive aromas are desired.

In addition to its use in the synthesis of chemicals and fragrances, 6,6-dimethyl-bicyclo[3.1.1]heptane-2-ethanol has also been studied for its potential in medicinal chemistry. The compound's bicyclic structure, along with the hydroxyl group, makes it a candidate for research into the development of bioactive molecules. Although specific therapeutic applications are still being explored, compounds with similar structures have been found to exhibit a variety of biological activities. Thus, 6,6-dimethyl-bicyclo[3.1.1]heptane-2-ethanol holds promise as a scaffold for developing new pharmaceuticals.

Moreover, its applications extend to the field of materials science, where the compound can be used to create novel materials with specific mechanical or chemical properties. The rigidity of the bicyclic structure and the reactivity of the hydroxyl group offer opportunities for designing materials with controlled properties for use in various industrial applications, such as coatings, adhesives, and polymers.

In conclusion, 6,6-dimethyl-bicyclo[3.1.1]heptane-2-ethanol is an important compound in organic synthesis, with applications in chemical manufacturing, fragrance production, medicinal chemistry, and materials science. Its unique bicyclic structure, coupled with the presence of a hydroxyl group, makes it a versatile intermediate for the development of various bioactive molecules and specialty chemicals. As research continues, the compound may find additional uses in the development of new compounds with unique properties and applications across various industries.

References

2023. Design, synthesis and antifungal evaluation of novel nopol derivatives as potent laccase inhibitors. Pest Management Science, 79(7).
DOI: 10.1002/ps.7426

2021. Nopol-Based Quinoline Derivatives as Antiplasmodial Agents. Molecules (Basel, Switzerland), 26(4).
DOI: 10.3390/molecules26041008

2017. Biological properties of Hertia cheirifolia L. flower extracts and effect of the nopol on α-glucosidase. International Journal of Biological Macromolecules, 95.
DOI: 10.1016/j.ijbiomac.2016.12.008
Market Analysis Reports
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