254892-87-0

Usage

Properties

highly reactive, potentially toxic

Uses

organic synthesis, precursor in chemical production

Structure

contains a cyclobutanone ring with two chlorine atoms and a bromophenyl group

Common applications

building block in pharmaceuticals, agrochemicals, fine chemicals

Importance of caution

reactivity and potential toxicity require careful handling in laboratory and industrial settings.

Upstream product

• 2039-82-9 1-bromo-4-ethenyl-benzene 
• 76-02-8 trifluoroacetyl chloride 
• 1122-91-4 4-bromo-benzaldehyde 

Downstream Products

• 254892-91-6 3-(4-bromophenyl)cyclobutanone 
• 1183047-51-9 3-(4-bromophenyl)cyclobutanol 
• 1033082-32-4 (-)-(R)-4-(4-bromophenyl)dihydrofuran-2(3H)-one 
• 1236357-60-0 1-bromo-4-(3,3-difluorocyclobutyl)benzene 
• 29924-39-8 β-(4-bromophenyl)-γ-butyrolactone 
• 254893-07-7 C₁₂H₁₃BN₂O₄ 
• 254892-99-4 3-(4-boronophenyl)cyclobutanone ethylene ketal 
• 254893-03-3 3-(4-boronophenyl)cyclobutanone 
• 254892-95-0 3-(4-bromophenyl)cyclobutanone ethylene ketal 
• 254892-82-5 1-amino-3-(4-dihydroxyborylphenyl)cyclobutanecarboxylic acid 

Relevant academic research and scientific papers

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.

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.

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.

Metal-Free sp3 C-SCF3 Coupling Reactions between Cycloketone Oxime Esters and S-trifluoromethyl 4-Methylbenzenesulfonothioate

A novel sp3 C-SCF3 coupling reaction between cycloketone oxime esters and S-trifluoromethyl 4-methylbenzenesulfonothioate was achieved. Ethanol was found to facilitate this transformation by trapping the sulfonyl cation. The metal-free and photocatalyst-free reaction conditions, as well as the broad substrate scope, make this a green protocol for the synthesis of SCF3-substituted nitriles.

COMPOUNDS USEFUL IN MODULATING THE FARNESOID X RECEPTOR AND METHODS OF MAKING AND USING THE SAME

Provided are compounds that can act as a modulator of a farnesoid X receptor (FXR) and that can be useful in the treatment of diseases and/or disorders associated with the FXR. Compositions including such compounds are also provided along with methods for preparing compounds of the present invention and their use.

Copper-catalyzed ring-opening C(sp3)-N coupling of cycloketone oxime esters: Access to 1°, 2° and 3° alkyl amines

A novel copper-catalyzed C(sp3)-N coupling of cycloketone oxime esters with nitrogen nucleophiles has been realized. All of the N-aryl/alkylanilines, anilines and benzophenone imine could be employed in this protocol to produce a variety of 1°, 2° and 3° alkyl amines in one or two steps. These resultant cyano-containing alkyl amines were proven to be versatile synthetic building blocks in a variety of chemical transformations.

Photoredox-Catalyzed Sulfonylation of O-Acyl Oximes via Iminyl Radicals with the Insertion of Sulfur Dioxide

A multicomponent sulfonylation of O-acyl oximes via iminyl radicals with the insertion of sulfur dioxide under photoredox catalysis is achieved. This multicomponent reaction of O-acyl oximes, potassium metabisulfite, alkenes, and nucleophiles under visible-light irradiation is efficient, giving rise to a range of sulfones in moderate to good yields. A broad reaction scope is presented with good functional group compatibility.

Photocatalytic Neophyl Rearrangement and Reduction of Distal Carbon Radicals by Iminyl Radical-Mediated C?C Bond Cleavage

The control of selectivity in the reactions of the highly reactive open-shell carbon radicals is an attractive but often challenging task. Building on the strategy of photoinduced iminyl radical-mediated C?C bond cleavage, we have developed photocatalytic neophyl rearrangement and reduction of distal carbon radicals under visible light irradiation of O-acyl oximes. This mild protocol tolerates a wide range of readily available O-acyl oximes, enabling facile synthesis of diversely substituted α,β-unsaturated nitriles and β-functionalized saturated nitriles in a highly selective manner. (Figure presented.).

THIENOPYRIDINE CARBOXAMIDES AS UBIQUITIN-SPECIFIC PROTEASE INHIBITORS

The disclosure relates to inhibitors of USP28 and/or USP25 useful in the treatment of cancers, inflammation, autoimmune diseases, and infectious diseases, having the Formula (I), where R1, R2, R3, R4, R5, R5', R6, R7, X, m, and n are described herein.