2972-05-6

Basic information

• Product Name: Cyclobutane-1-one oxime
• Synonyms: Cyclobutane-1-one oxime;Cyclobutanone oxime
• CAS NO: 2972-05-6
• Molecular Formula: C₄H₇NO
• Molecular Weight: 85.11
• Mol File: 2972-05-6.mol

Chemical Properties

• Melting Point: 81-82 °C
• Boiling Point: 173.4±9.0 °C(Predicted)
• Appearance: /
• Density: 1.22±0.1 g/cm3(Predicted)
• PKA: 12.42±0.20(Predicted)
• CAS DataBase Reference: Cyclobutane-1-one oxime(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclobutane-1-one oxime(2972-05-6)
• EPA Substance Registry System: Cyclobutane-1-one oxime(2972-05-6)

Safety Data

• Hazardous Substances Data: 2972-05-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Cyclobutane-1-one oxime is used as a reagent for the synthesis of various nitrogen-containing pharmaceuticals. Its ability to undergo nucleophilic addition and substitution reactions makes it a valuable building block in the development of new drugs.
Used in Agrochemical Industry:
Cyclobutane-1-one oxime is used as a reagent in the synthesis of nitrogen-containing herbicides and insecticides. Its versatility in organic chemistry allows for the creation of effective and targeted agrochemicals.
Used in Coordination Chemistry:
Cyclobutane-1-one oxime is used as a ligand in coordination chemistry, forming stable complexes with metal ions. This application is important in the development of new materials and catalysts with specific properties and functions.

Upstream product

• 287-23-0 cyclobutane 
• 1191-95-3 cyclobutanone 

Relevant articles and documents

β-lactam synthesis via copper-catalyzed directed aminoalkylation of unactivated alkenes with cyclobutanone O-benzoyloximes

A new protocol for amide-directed Cu-catalyzed aminoalkylation of unactivated alkenes using cyclobutanone oxime esters as alkyl radical donors is developed. Both primary and secondary alkyl groups can be selectively installed at the C4 position of termina

Synthesis of β-nitro ketones from geminal bromonitroalkanes and silyl enol ethers by visible light photoredox catalysis

Various β-nitro ketones, including those bearing a β-tertiary carbon, were prepared from geminal bromonitroalkanes and trimethylsilyl enol ethers of a broad range of ketones by visible light photoredox catalysis, which were then easily converted into β-amino ketones, 1,3-amino alcohols, α,β-unsaturated ketones, β-cyano ketones and γ-nitro ketones.

Electro-reductive C-H cyanoalkylation of quinoxalin-2(1H)-ones

Herein, we report a practical electro-reductive protocol for the direct C–H cyanoalkylation of quinoxalin-2(1H)-ones via iminyl radical-mediated ring opening. These mild reactions proceed under metal-, reductant-, and reagent-free conditions to provide synthetically useful cyanoalkylated quinoxalin-2(1H)-ones.

Enantioselective Iridium-Catalyzed Allylation of Nitroalkanes: Entry to β-Stereogenic α-Quaternary Primary Amines

The first systematic study of simple nitronate nucleophiles in iridium-catalyzed allylic alkylation is described. Using a tol-BINAP-modified π-allyliridiumC,O-benzoate catalyst, α,α-disubstituted nitronates substitute racemic branched alkyl-substituted al

Nickel-Catalyzed Favorskii-Type Rearrangement of Cyclobutanone Oxime Esters to Cyclopropanecarbonitriles

A nickel-catalyzed base-promoted rearrangement of cyclobutanone oxime esters to cyclopropanecarbonitriles was developed. The ring opening of cyclobutanone oxime esters occurs at the sterically less hindered side. A base-promoted nickelacyclobutane intermediate, formed in situ, is assumed to be involved in the formation of the product.

Synthesis of Phenanthridine and Quinoxaline Derivatives via Copper-Catalyzed Radical Cyanoalkylation of Cyclobutanone Oxime Esters and Vinyl Azides

A copper-catalyzed radical cyclization of cyclobutanone oxime esters and vinyl azide is described. This method provides facile access to cyanoalkyl-substituted phenanthridines and quinoxalines with excellent isolated yields. Moreover, these reactions proceed under mild conditions with a board substrate scope and excellent functional group tolerance.

Copper-Catalyzed Sulfonylation of Cyclobutanone Oxime Esters with Sulfonyl Hydrazides

A copper-catalyzed radical cross-coupling of cyclobutanone oxime esters with sulfonyl hydrazides has been developed. The copper-based catalytic system proved crucial for cleavage of the C-C bond of cyclobutanone oximes and for selective C-S bond-formation involving persistent sulfonyl-metal radical intermediates. This protocol is distinguished by the low-cost catalytic system, which does not require ligand, base, or toxic cyanide salt, and by the use of readily accessible starting materials, as well as broad substrate scope, providing an efficient approach to various diversely substituted cyano-containing sulfones.

Metal-free chalcogenation of cycloketone oxime esters with dichalcogenides

We report the metal-free chalcogenation of cycloketone oxime esters with dichalcogenides via a radical process. Because of the metal-free condition and use of readily accessible dichalcogenides, this method is an effective and green strategy for the synthesis of chalcogen-substituted butyronitrile.

Visible-Light-Promoted Selenocyanation of Cyclobutanone Oxime Esters Using Potassium Selenocyanate

We report the visible-light-promoted selenocyanation of cyclobutanone oxime esters using potassium selenocyanate in the presence of a fac-Ir(ppy)3 catalyst for the first time. Because of the mild conditions employed and use of readily accessible potassium selenocyanate, this method is an effective and green strategy for the synthesis of cyano and selenocyano bifunctional substituted alkanes.

Dual Nickel/Ruthenium Strategy for Photoinduced Decarboxylative Cross-Coupling of α,β-Unsaturated Carboxylic Acids with Cycloketone Oxime Esters

Herein, a dual nickel/ruthenium strategy is developed for photoinduced decarboxylative cross-coupling between α,β-unsaturated carboxylic acids and cycloketone oxime esters. The reaction mechanism is distinct from previous photoinduced decarboxylation of α,β-unsaturated carboxylic acids. This reaction might proceed through a nickelacyclopropane intermediate. The C(sp2)-C(sp3) bond constructed by the aforementioned reaction provides an efficient approach to obtaining various cyanoalkyl alkenes, which are synthetically valuable organic skeletons in organic and medicinal chemistry, under mild reaction conditions. The protocol tolerates many critical functional groups and provides a route for the modification of complex organic molecules.