13866-28-9

Basic information

• Product Name: Cyclobutanone, 2,2-dichloro-3-phenyl-
• CAS NO: 13866-28-9
• Molecular Formula: C10H8Cl2O
• Molecular Weight: 215.079
• Mol File: 13866-28-9.mol
• Article Data: 41

Chemical Properties

• CAS DataBase Reference: Cyclobutanone, 2,2-dichloro-3-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclobutanone, 2,2-dichloro-3-phenyl-(13866-28-9)
• EPA Substance Registry System: Cyclobutanone, 2,2-dichloro-3-phenyl-(13866-28-9)

Safety Data

• Hazardous Substances Data: 13866-28-9(Hazardous Substances Data)

Usage

General Description

Cyclobutanone, 2,2-dichloro-3-phenyl- is a chemical compound with the molecular formula C10H9Cl2O. It is a colorless to light yellow liquid with a faint odor, and is commonly used as an intermediate in the production of pharmaceuticals and agrochemicals. Cyclobutanone, 2,2-dichloro-3-phenyl- is also known to have applications in research and development, as well as in the manufacturing of other organic chemicals. Its structural properties and functional groups make it a versatile building block for the synthesis of various organic compounds, and it is important for its contribution to the pharmaceutical and chemical industries. However, like all chemicals, proper precautions should be taken when handling this substance to prevent any potential health or environmental hazards.

Upstream product

• 100-42-5 styrene 
• 4591-28-0 dichloroketene 
• 76-02-8 trifluoroacetyl chloride 
• 100-52-7 benzaldehyde 
• 74-85-1 ethene 
• 536-74-3 phenylacetylene 

Downstream Products

• 2819-12-7 trans-2-methyl-3-phenylcyclopentan-1-one 
• 131388-01-7 2-methyl-4-phenylcyclopentanone 
• 52784-31-3 3-Phenylcyclobutanone 
• 136527-32-7 4,4-dichloro-3-phenylbutyric acid 
• 78920-22-6 5-hydroxy-4-phenyl-4,5-dihydro-3H-furan-2-one 
• 124908-82-3 2-chloro-3-phenyl-1-cyclobuten-1-yl-acetate 
• 718599-09-8 4,4-dichloro-3-phenyl-N-propyl-butyramide 
• 51965-98-1 2,2,4-trichloro-3-phenylcyclobutenone 
• 708-10-1 3-phenyl-4-hydroxycyclobut-3-ene-1,2-dione 
• 146514-41-2 1-Isopropylidene-3-phenylcyclobutane 

Relevant articles and documents

Stereoselective synthesis of cis-2-aryl- and 2-alkyl-1-chlorocyclopropanecarboxaldehydes

The title compounds were stereoselectively synthesized via a semi-benzilic Favorskii rearrangement of 3-aryl- and 3-alkyl-2,2-dichlorocyclobutanols, obtained by stereoselective reduction of the corresponding cyclobutanones. This synthetic pathway, starting from the synthesis of 3-substituted-2,2-dichlorocyclobutanones can be performed in one day with total yields up to 60% after purification. Reduction of the cyclobutanones yielded only cis-3-substituted cyclobutanols. Taking into account the stereoselectivity of the rearrangement, 1-halocyclopropanecarboxaldehydes, of which very few articles have been published, can be seen as highly interesting building blocks for further elaboration.

Radical C-C Bond Cleavage/Addition Cascade of Benzyl Cycloketone Oxime Ethers Enabled by Photogenerated Cyclic Iminyl Radicals

A light-driven, metal-free, and iminyl radical-mediated ring-opening C-C bond cleavage/addition cascade of O-4-methoxybenzyl oxime ethers and alkenes is described for the first time. The reaction shows a broad substrate scope and high functional group compatibility with both components, giving the corresponding valuable oxo nitriles in generally good yields. Key to the success of this protocol is the generation of cyclic iminyl radicals from the O-4-methoxybenzyl oxime ethers via a photocatalytic hydrogen atom transfer (HAT) process. The proposed main pathway is also supported by the preliminary mechanistic studies.

Manganese=Catalyzed Achmatowicz Rearrangement Using Green Oxidant H2O2

Oxidation reactions have been extensively studied in the context of the transformations of biomass=derived furans. However, in contrast to the vast literature on utilizing the stoichiometric oxidants, such as m=CPBA and NBS, catalytic methods for the oxidative furan=recyclizations remain scarcely investigated. Given this, we report a means of manganese=catalyzed oxidations of furan with low loading, achieving the Achmatowicz rearrangement in the presence of hydrogen peroxide as an environmentally benign oxidant under mild conditions with wide functional group compatibility.

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.