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Cyclobutanone
[CAS# 1191-95-3]

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Identification
Classification Chemical reagent >> Organic reagent >> Fatty ketone (including enol)
Name Cyclobutanone
Molecular Structure CAS # 1191-95-3, 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 ºC
Boiling point 99 ºC
Refractive index 1.4205-1.4225
Flash point 10 ºC
Water solubility INSOLUBLE
Safety Data
Hazard Symbols symbol   GHS02 Danger    Details
Hazard Statements H225-H226    Details
Precautionary Statements P210-P233-P240-P241-P242-P243-P280-P303+P361+P353-P370+P378-P403+P235-P501    Details
Hazard Classification
up    Details
HazardClassCategory CodeHazard Statement
Flammable liquidsFlam. Liq.3H226
Flammable liquidsFlam. Liq.2H225
Skin irritationSkin Irrit.2H315
Specific target organ toxicity - single exposureSTOT SE3H335
Eye irritationEye Irrit.2AH319
Transport Information UN 1224
SDS Available
up Discovory and Applicatios
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.
Market Analysis Reports
List of Reports Available for Cyclobutanone
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