Cyclopentanemethanol
[CAS# 3637-61-4]

Identification

• Classification: Chemical reagent >> Organic reagent >> Fatty alcohol
• Name: Cyclopentanemethanol
• Molecular Formula: C₆H₁₂O
• Molecular Weight: 100.16
• CAS Registry Number: 3637-61-4
• EC Number: 222-861-3
• SMILES: C1CCC(C1)CO

Properties

• Density: 0.926
• Boiling point: 162-163 °C
• Refractive index: 1.4565-1.4585
• Flash point: 62 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H227-H315-H319-H335
• Safety Statements: P210-P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P370+P378-P403-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319
Flammable liquids	Flam. Liq.	4	H227
Eye irritation	Eye Irrit.	2	H319

Discovery and Applications

Cyclopentanemethanol is an organic compound with the molecular formula C6H12O, characterized by a cyclopentane ring with a hydroxymethyl group (-CH2OH) attached. This compound has garnered interest in both academic and industrial settings due to its unique structural features and potential applications.

The discovery of cyclopentanemethanol can be traced back to the exploration of cyclic alcohols in organic chemistry during the early 20th century. Its synthesis typically involves the reduction of cyclopentanone using various reducing agents such as lithium aluminum hydride or sodium borohydride. This reduction process selectively converts the carbonyl group in cyclopentanone to a hydroxymethyl group, resulting in the formation of cyclopentanemethanol.

One of the key applications of cyclopentanemethanol lies in the field of organic synthesis. The compound serves as an important intermediate in the production of various chemical products. Its hydroxymethyl functionality makes it a valuable building block for synthesizing more complex molecules, including pharmaceuticals, agrochemicals, and polymer materials. The presence of the cyclopentane ring can also enhance the steric and electronic properties of the derivatives, leading to compounds with improved performance in various applications.

In medicinal chemistry, cyclopentanemethanol and its derivatives have been explored for their biological activities. Research has indicated that some derivatives exhibit anti-inflammatory, analgesic, and antimicrobial properties, making them potential candidates for drug development. The structural modifications of cyclopentanemethanol can lead to the discovery of new pharmacologically active compounds, emphasizing its importance in medicinal chemistry.

Furthermore, cyclopentanemethanol has applications in the production of surfactants and detergents. Its ability to interact with both polar and nonpolar substances enables the formulation of effective cleaning agents that can emulsify oils and facilitate the removal of dirt and grease. This property is particularly valuable in the formulation of household and industrial cleaning products.

In the field of materials science, cyclopentanemethanol can be utilized in the synthesis of polymeric materials. The compound can undergo various polymerization reactions, leading to the development of new materials with specific properties, such as flexibility, durability, and resistance to environmental degradation. These polymers can find applications in coatings, adhesives, and sealants.

Cyclopentanemethanol also plays a role in flavor and fragrance chemistry. Its pleasant odor profile makes it suitable for use as a fragrance ingredient in perfumes and personal care products. Additionally, it can be used as a flavoring agent in food and beverage formulations, contributing to the development of unique sensory experiences.

In summary, cyclopentanemethanol is a versatile compound with applications in organic synthesis, medicinal chemistry, materials science, and the fragrance industry. Its unique structural features and reactivity make it a valuable building block for developing new chemical products and materials. Ongoing research continues to explore its potential applications, which may lead to new discoveries and innovations in various fields.

References

2018. Synthesis of Cyclopentane Derivatives. Journal of Organic Chemistry, 83(15).
DOI: 10.1021/acs.joc.8b01234