4203-30-9

Usage

Uses

Used in Organic Synthesis:
Ethanone, 1-(4-bromophenyl)-2-diazois used as a diazo reagent for the generation of carbene species in organic synthesis. The carbene species are versatile intermediates that can participate in a variety of reactions, such as cyclopropanation, cycloaddition, and nucleophilic addition. Ethanone, 1-(4-bromophenyl)-2-diazo-'s bromophenyl group serves as a good leaving group, enabling the formation of new carbon-carbon or carbon-heteroatom bonds.
Used in Chemical Reactions:
In the field of chemical reactions, Ethanone, 1-(4-bromophenyl)-2-diazois employed to facilitate the formation of new chemical bonds through its reactive diazo group. Its ability to generate carbene species allows for the participation in various types of reactions, expanding the scope of synthetic chemistry and enabling the creation of complex molecular structures.
Safety Precautions:
Due to the high reactivity and potential explosiveness of the diazo group in Ethanone, 1-(4-bromophenyl)-2-diazo-, it is crucial to implement appropriate safety measures during its use. This includes careful handling, proper storage, and adherence to safety protocols to minimize the risk of accidents and ensure the safe conduct of chemical reactions involving Ethanone, 1-(4-bromophenyl)-2-diazo-.

Upstream product

• 586-76-5 4-Bromobenzoic acid 
• 33170-68-2 1,3-bis-(4-bromo-phenyl)-propane-1,3-dione 
• 80352-42-7 1-(4-bromophenyl)-2,2-dihydroxyethanone 
• 99-73-0 para-bromophenacyl bromide 
• 99-90-1 para-bromoacetophenone 
• 14153-75-4 p-bromobenzoylacetaldehyde 
• 53073-03-3 sodium salt of p-bromobenzoylacetaldehyde 
• 23722-26-1 p-Brom-phenylglyoxal-2-hydrazon 
• 186581-53-3 diazomethane 
• 586-75-4 4-chlorobenzoyl chloride 
• 71559-14-3 2-azido-1-(4-bromophenyl)ethanone 

Downstream Products

• 23725-87-3 1-(4-bromo-phenyl)-2-isovaleryloxy-ethanone 
• 806-98-4 succinic acid bis-(4-bromo-phenacyl ester) 
• 98475-05-9 α-tosyloxy-4-bromoacetophenone 
• 7500-37-0 2-(4-bromophenyl)-2-oxoethyl acetate 
• 14041-01-1 p-bromophenacyl propionate 
• 100622-65-9 benzenesulfonic acid-(4-bromo-phenacyl ester) 
• 14622-29-8 p-bromophenacyl 2-hydroxybenzoate 
• 5611-17-6 2-(4-bromophenyl)-2-oxoethyl butyrate 
• 93897-42-8 2-(4-bromophenyl)-2-oxoethyl-4-nitrobenzoate 
• 69163-85-5 2-methyl-5-(4-bromophenyl)-1,3-oxazole 
• 77901-31-6 1-(4-Bromo-phenyl)-2-(2,4,6-trimethoxy-phenyl)-ethanone 
• 77901-41-8 N-[(Z)-2-(4-Bromo-phenyl)-2-(2,4,6-trimethoxy-phenyl)-vinyl]-acetamide 
• 77901-36-1 N-[(E)-2-(4-Bromo-phenyl)-2-(2,4,6-trimethoxy-phenyl)-vinyl]-acetamide 
• 96845-77-1 (4-Bromo-phenylethynyloxy)-triisopropyl-silane 

Relevant academic research and scientific papers

Practical Application of the Aqueous 'Sulfonyl-Azide-Free' (SAFE) Diazo Transfer Protocol to Less α-C-H Acidic Ketones and Esters

The earlier described 'sulfonyl-Azide-free' ('SAFE') protocol for diazo transfer to CH-Acidic 1,3-dicarbonyl compounds (and their similarly activated congeners) has been extended to the less reactive monocarbonyl substrates, which previously required a se

Site-Selective Conversion of Azido Groups at Carbonyl α-Positions to Diazo Groups in Diazido and Triazido Compounds

This paper reports on the selective conversion of alkyl azido groups at the carbonyl α-position to diazo compounds. Through β-elimination of dinitrogen, followed by hydrazone formation/decomposition, α-azidocarbonyl moieties were transformed into α-diazo carbonyl groups in one step. As these reaction conditions do not involve aryl or general alkyl azides, site-selective conversions of di- and triazides were achieved. Through this method, the successive site-selective conjugation of the triazido molecule with three different components is demonstrated.

Phosphoric Acid Catalyzed [4 + 1]-Cycloannulation Reaction of ortho-Quinone Methides and Diazoketones: Catalytic, Enantioselective Access toward cis-2,3-Dihydrobenzofurans

A highly straightforward route to enantiomerically highly enriched cis-2,3-dihydrobenzofurans has been achieved via addition of α-diazocarbonyl compounds to in situ generated o-QMs catalyzed by a chiral Br?nsted acid. This catalytic strategy provides a direct access to 2,3-dihydrobenzofurans in high yields and with up to 91:9 dr and 99:1 er at ambient temperature. Moreover, a unique phenonium-type rearrangement accounts for product formation with an inverted 2,3-substitution pattern.

Radical Cation Cyclopropanations via Chromium Photooxidative Catalysis

The chromium photocatalyzed cyclopropanation of diazo reagents with electron-rich alkenes is described. The transformation occurs under mild conditions and features specific distinctions from traditional diazo-based cyclopropanations (e.g., avoiding β-hydride elimination, chemoselectivity considerations, etc.). The reaction appears to work most effectively using chromium catalysis, and a number of decorated cyclopropanes can be accessed in generally good yields.

Tandem Synthesis of α-Diazoketones from 1,3-Diketones

A highly efficient synthesis of α-diazoketone was achieved by simply stirring the mixture of 1,3-diketone, TsN3, and MeNH2 in EtOH. It was a tandem reaction including a novel primary amine-catalyzed Regitz diazo transfer of 1,3-diket

Facile access to 2,2-disubstituted indolin-3-ones: Via a cascade Fischer indolization/Claisen rearrangement reaction

An efficient approach for the synthesis of 2,2-disubstituted indolin-3-ones is described. From readily accessible aryl hydrazines and allyloxyketones, 2,2-disubstituted indolin-3-ones could be obtained in good to excellent yields under mild reaction condi

One-pot synthesis of polyfunctional pyrazoles: An easy access to α-diazoketones from arylglyoxal monohydrates and tosylhydrazine

A new and efficient method for the generation of α-diazoketones has been developed from arylglyoxal monohydrates and tosylhydrazine at room temperature. 1,3-Dipolar cycloaddition reactions were used to constructing polyfunctional pyrazole derivatives by the reaction of generated α-diazoketones in situ with electron-deficient alkenes, quinones and coumarins in one pot. The one-dimensional molecular packing of 1H-benzo[f]indazole-4,9-dione derivatives along the c direction demonstrated a helical chain formation via N-H?O hydrogen-bonding.

Rhodium(II)-catalyzed cross-coupling of diazo compounds

Nothing left to chance: A convenient protocol for selective cross-coupling of diazo compounds for the convergent synthesis of alkenes was developed (see scheme; EDG=aryl, heteroaryl, vinyl; R=O-alkyl, aryl). The selectivity control elements were identifie

A cascade approach to pyridines from 2-Azido-2,4-dienoates and α-diazocarbonyl compounds

A one-pot synthesis of substituted pyridines via a cascade reaction of 2-azido-2,4-dienoates with α-diazocarbonyl compounds and triphenylphosphine is reported. The process involves a Staudinger-Meyer reaction, a Wolff rearrangement, an aza-Wittig reaction, and an electrocyclic ring- closure. The procedure is general and efficient. The substrates are readily available.

Formation of fulleroids as major products and application of solid state reaction in the functionalization of 60|fullerene by aromatic diazoketones

The reactions of various aromatic diazoketones with [60]fullerene were investigated in solution (o-dichlorobenzene) or in the solid-state. Under all the conditions examined, the fulleroid with the methine proton located over a six-membered ring was obtain