Cyclopentanecarbaldehyde
[CAS# 872-53-7]

Identification

• Classification: Chemical reagent >> Organic reagent >> Fatty aldehyde (containing acetal, hemiacetal)
• Name: Cyclopentanecarbaldehyde
• Molecular Formula: C₆H₁₀O
• Molecular Weight: 98.14
• CAS Registry Number: 872-53-7
• EC Number: 212-829-7
• SMILES: C1CCC(C1)C=O

Properties

• Density: 0.919
• Boiling point: 140-141 °C
• Refractive index: 1.4430
• Flash point: 83 °F

Safety Data

• Hazard Symbols: GHS02;GHS07 Warning
• Risk Statements: H226-H315-H319-H335
• Safety Statements: P210-P233-P240-P241-P242-P243-P261-P264-P264+P265-P271-P280-P302+P352-P303+P361+P353-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P370+P378-P403+P233-P403+P235-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Flammable liquids	Flam. Liq.	3	H226
Eye irritation	Eye Irrit.	2A	H319

• Transport Information: UN 1989

Discovery and Applications

Cyclopentanecarboxaldehyde is an important organic intermediate widely used in organic synthesis, flavoring and fragrance industries. Cyclopentanecarboxaldehyde was first synthesized in the early 20th century, stemming from the exploration of cyclic hydrocarbon aldehydes. Aldehydes are organic compounds containing a carbonyl group and an organic substituent bound to a hydrogen atom. The discovery involved the oxidation or direct cyclization of cyclopentanol.

One common method for its preparation is the oxidation of cyclopentanol using reagents such as chromic acid or PCC (pyridinium chlorochromate). Another method is hydroformylation, where cyclopentene reacts with carbon monoxide and hydrogen in the presence of a catalyst to form cyclopentanecarboxaldehyde. The product consists of a five-membered cyclopentane ring attached to an aldehyde group and is a colorless liquid that is moderately soluble in water; highly soluble in organic solvents such as ethanol and diethyl ether.

Cyclopentanecarboxaldehyde is used as an intermediate in the synthesis of various pharmaceuticals. Its reactivity allows it to be used in further reactions such as aldol condensation, Grignard reaction, and reductive amination to form complex molecules.

It is used in the production of fine chemicals and agrochemicals. Its cyclic structure allows for the creation of a range of derivatives for different chemical applications.

Cyclopentane carboxaldehyde is valued for its unique, pleasant odor, described as green, floral, or woody. It is used in perfume, flavor, and fragrance formulations to add fragrance to a variety of consumer products. Its aroma properties make it an ingredient in food and beverage flavorings, enhancing the taste with its unique aroma properties.

It can be used to make specialized polymers. Its aldehyde group allows for polymerization or copolymerization, resulting in materials with desired physical and chemical properties.

Cyclopentane carboxaldehyde is used in the synthesis of resins and coatings, providing enhanced durability and chemical resistance to a variety of surfaces. Its reactivity with amines and other functional groups makes it a useful ingredient in resin formulations.

Cyclopentane carboxaldehyde is used in academic and industrial research to explore new chemical reactions and develop novel compounds. Its structure makes it an excellent candidate for studying reaction mechanisms and developing new synthetic methods. It is used to study cyclic aldehydes and their reactions, helping to understand chemical behavior in ring systems and providing insights for the development of new cyclic compounds.

Cyclopentane carboxaldehyde should be handled with care. It is flammable and should be stored in a cool, dry place away from sources of ignition. Adequate ventilation, protective clothing, and goggles are recommended to prevent exposure when handling this compound.

References

2024. Iron-Catalyzed Functionalization of Heterocycles Through C-H Activation. Functionalisation of Heterocycles through Transition Metal Catalyzed C-H Activation, 74.
DOI: 10.1007/7081_2024_74

2021. Improving the thermal stability of poly(cyclohexylene carbonate) by in situ end-capping. Polymer Bulletin, 78(12).
DOI: 10.1007/s00289-021-03792-w

2005. Atmospheric Chemistry of C3-C6 Cycloalkanecarbaldehydes. The journal of physical chemistry. A, 109(20).
URL: https://pubmed.ncbi.nlm.nih.gov/16833864