Cyclobutanone
[CAS# 1191-95-3]

Identification

• Classification: Chemical reagent >> Organic reagent >> Fatty ketone (including enol)
• Name: Cyclobutanone
• Molecular Formula: C₄H₆O
• Molecular Weight: 70.09
• CAS Registry Number: 1191-95-3
• EC Number: 214-745-6
• SMILES: C1CC(=O)C1

Properties

• Density: 0.938
• Melting point: -50.9 °C
• Boiling point: 99 °C
• Refractive index: 1.4205-1.4225
• Flash point: 10 °C
• Water solubility: INSOLUBLE

Safety Data

• Hazard Symbols: GHS02 Danger
• Risk Statements: H225-H226
• Safety Statements: P210-P233-P240-P241-P242-P243-P280-P303+P361+P353-P370+P378-P403+P235-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Flammable liquids	Flam. Liq.	3	H226
Flammable liquids	Flam. Liq.	2	H225
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319

• Transport Information: UN 1224

Discovery and Applications

Cyclobutanone, an organic compound with the formula C4H6O, is a four-membered cyclic ketone first synthesized in the mid-20th century. Its discovery is attributed to advances in organic chemistry that allowed for the exploration of small ring compounds. The synthesis of cyclobutanone often involves the cyclization of suitable precursors, such as butadiene derivatives, under controlled conditions. Its strained ring structure and unique reactivity made it a compound of interest for chemists studying ring strain and reactivity in small cyclic molecules.

Cyclobutanone is a valuable intermediate in organic synthesis due to its strained ring system, which makes it highly reactive. It is used as a precursor in the synthesis of more complex molecules through ring-opening reactions, nucleophilic additions, and rearrangements. Its reactivity enables the construction of larger ring systems and polycyclic compounds.

In pharmaceuticals the strained ring of cyclobutanone can be modified to create a variety of bioactive molecules with potential therapeutic properties. Researchers investigate cyclobutanone-based compounds for their ability to inhibit enzymes, act as intermediates in drug synthesis, and serve as scaffolds for developing new drugs. The unique structure of cyclobutanone can impart desirable pharmacokinetic properties.

Cyclobutanone is used in the development of advanced materials, particularly in the field of polymer chemistry. Its ring strain and reactivity make it a useful monomer for producing high-performance polymers with specific mechanical and thermal properties. Cyclobutanone derivatives are also explored for their potential use in creating smart materials and responsive polymers.

In academic research, cyclobutanone is a model compound for studying the effects of ring strain on reactivity and stability. Its unique properties provide insights into the behavior of small ring compounds and the factors influencing their chemical transformations. Researchers use cyclobutanone to investigate mechanisms of ring-opening reactions, stereoelectronic effects, and the development of new synthetic methodologies.

Cyclobutanone's structure makes it an interesting subject in photochemical studies. Under ultraviolet (UV) light, cyclobutanone can undergo various photochemical reactions, including ring expansion and rearrangement. These photoreactions are studied to develop new photoresponsive materials and understand the principles of photochemistry. Applications of photochemical transformations of cyclobutanone include the design of light-activated drugs and materials with tunable properties.

References

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2010. Tocotrienols inhibit lipopolysaccharide-induced pro-inflammatory cytokines in macrophages of female mice. Lipids in Health and Disease.
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