3-Oxocyclobutanecarbonitrile
[CAS# 20249-16-5]

Identification

• Classification: Organic raw materials >> Nitrile compound
• Name: 3-Oxocyclobutanecarbonitrile
• Molecular Formula: C₅H₅NO
• Molecular Weight: 95.10
• CAS Registry Number: 20249-16-5
• EC Number: 867-362-7
• SMILES: C1C(CC1=O)C#N

Properties

• Density: 1.1±0.1 g/cm³ Calc.^*
• Boiling point: 249.1±33.0 °C 760 mmHg (Calc.)^*
• Flash point: 104.5±25.4 °C (Calc.)^*
• Index of refraction: 1.464 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS06 Danger
• Risk Statements: H301-H311-H331
• Safety Statements: P261-P262-P264-P270-P271-P280-P301+P316-P302+P352-P304+P340-P316-P321-P330-P361+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	3	H311
Acute toxicity	Acute Tox.	3	H301
Acute toxicity	Acute Tox.	3	H331

Discovery and Applications

3-Oxocyclobutanecarbonitrile is an organic chemical compound with the molecular formula C6H7NO2. It belongs to the class of compounds known as cyclobutanes, which are characterized by a four-membered ring structure. In this particular compound, the cyclobutane ring is substituted with both a carbonyl group and a nitrile group, making it a versatile intermediate in organic synthesis.

The compound is notable for its potential applications in organic chemistry, particularly in the synthesis of more complex molecules. Its unique structure allows it to participate in a variety of chemical reactions, which are valuable in the production of pharmaceuticals, agrochemicals, and other specialty chemicals.

The synthesis of 3-oxocyclobutanecarbonitrile can be accomplished through several methods, typically involving the reaction of cyclobutene derivatives with reagents that introduce the carbonyl and nitrile groups. The compound's reactivity is primarily influenced by the electron-withdrawing nature of the nitrile group, which makes the carbonyl carbon more electrophilic and susceptible to nucleophilic attack.

The compound has been studied for its potential use as an intermediate in the synthesis of biologically active molecules. Specifically, it has been explored in the context of developing new drugs or compounds with antimicrobial, anti-inflammatory, or anticancer properties. Its ability to undergo various ring-opening reactions or nucleophilic substitutions makes it a key building block for constructing more complex structures.

In addition to its applications in drug discovery, 3-oxocyclobutanecarbonitrile has also been investigated for its role in material science. It can be used in the synthesis of polymer precursors, where its reactivity allows it to be incorporated into larger macromolecular structures.

While much of the research on 3-oxocyclobutanecarbonitrile is ongoing, it is already recognized as a useful compound in the toolkit of synthetic chemists. Its structure lends itself well to further modifications and optimizations for specific applications in the pharmaceutical and chemical industries.

References

2021. Synthesis of PF-06826647. Synfacts, (1).
DOI: 10.1055/s-0040-1719324

2018. Multigram Synthesis of C4/C5 3,3-Difluorocyclobutyl-Substituted Building Blocks. Synthesis, 50(16).
DOI: 10.1055/s-0037-1610237

2006. Cyclic Oxonitriles: Synergistic Juxtaposition of Ketone and Nitrile Functionalities. Synthesis, (18).
DOI: 10.1055/s-2006-926363