3884-71-7

Usage

Uses

Used in Pharmaceutical Industry:
5-BROMO-PENTAN-2-ONE is used as a key intermediate for the synthesis of various pharmaceuticals, contributing to the development of new drugs and therapeutic agents. Its unique chemical structure allows for the creation of a wide range of medicinal compounds with diverse applications in healthcare.
Used in Agrochemical Industry:
In the agrochemical sector, 5-BROMO-PENTAN-2-ONE serves as a building block for the production of various agrochemicals, including pesticides and herbicides. Its incorporation into these products helps improve their effectiveness in controlling pests and weeds, thereby enhancing crop yields and protecting agricultural resources.
Used in Advanced Materials Industry:
5-BROMO-PENTAN-2-ONE is utilized as a precursor in the synthesis of advanced materials, such as polymers, coatings, and composites. Its unique properties enable the development of innovative materials with improved performance characteristics, including enhanced durability, stability, and functionality.
Used in Fine Chemicals Production:
As a key intermediate in the manufacture of fine chemicals, 5-BROMO-PENTAN-2-ONE plays a vital role in the production of specialty chemicals used in various industries, including fragrances, dyes, and flavorings. Its versatility allows for the creation of a diverse range of high-quality fine chemicals that meet specific application requirements.
Used in Chemical Research:
In the field of chemical research, 5-BROMO-PENTAN-2-ONE is employed as a valuable compound for studying various chemical reactions and mechanisms. Its unique structure and reactivity make it an ideal candidate for exploring new synthetic pathways, understanding reaction kinetics, and developing novel chemical processes.
Precautions:
Due to the potential hazards associated with 5-BROMO-PENTAN-2-ONE, it is essential to follow proper handling and storage procedures. This includes using appropriate personal protective equipment, ensuring proper ventilation, and storing the compound in a cool, dry, and well-sealed container to minimize the risk of accidents and exposure.

InChI:InChI=1/C5H9BrO/c1-5(7)3-2-4-6/h2-4H2,1H3

Upstream product

• 31950-56-8 4-bromopent-1-ene 
• 1071-73-4 5-Hydroxy-2-pentanone 
• 1487-15-6 2-Methyl-4,5-dihydrofuran 
• 5891-21-4 5-chloro-2-pentanone 
• 765-43-5 Cyclopropyl methyl ketone 
• 100606-66-4 1,5-dibromopentan-2-ol 
• 20117-47-9 1-methylcyclobutanol 
• 32933-03-2 ethyl 1-acetylcyclopropanecarboxylate 
• 1119-51-3 bromopentene 
• 2623-87-2 bromobutyric acid 
• 917-54-4 methyllithium 
• 29021-98-5 3-(2-methyl-[1,3]dioxolan-2-yl)-propan-1-ol 
• 10035-10-6 hydrogen bromide 
• 4388-57-2 tert-butyldimethylsilyl 3-(2-methyl-1,3-dioxolan-2-yl)propanoate 

Downstream Products

• 691412-31-4 5-(ethyl-methyl-amino)-pentan-2-one 
• 89534-22-5 5-methylsulfanyl-pentan-2-one 
• 872-32-2 2-methyl-1H-pyrroline 
• 765-43-5 Cyclopropyl methyl ketone 
• 98321-74-5 5-mercaptopentan-2-one 
• 43018-61-7 1-N,N-dimethylaminopentan-4-one 
• 105-14-6 5-diethylamino-2-pentanone 
• 861077-19-2 5-anilino-pentan-2-one 
• 81358-55-6 5-(phenylsulfenyl)-2-pentanone 
• 821-55-6 2-Nonanone 
• 19679-75-5 cyano-2 methyl-2 tetrahydrofuranne 
• 16538-91-3 decane-2,9-dione 
• 92827-36-6 5--N-methylamino>pentan-2-one 
• 14171-89-2 1-phenyl-5-hexanone 

Relevant academic research and scientific papers

Energy Read-out as a Probe of Kinetically Hidden Transition States

The initial energy in a reactive intermediate is derived from the transition state before the intermediate but can affect selectivity after the intermediate. In this way an observable selectivity can report on a prior, kinetically hidden mechanistic step. This new type of mechanistic probe is demonstrated here for the oxidation of 1-methylcyclobutanol by phthaloyl peroxide/Bu4N+Br-, and it supports a hypobromite chain mechanism in place of the previously proposed hydrogen atom transfer mechanism.

Synthesis of two new enrichable and MS-cleavable cross-linkers to define protein-protein interactions by mass spectrometry

The cross-linking Mass Spectrometry (XL-MS) technique extracts structural information from protein complexes without requiring highly purified samples, crystallinity, or large amounts of material. However, there are challenges to applying the technique to protein complexes in vitro, and those challenges become more daunting with in vivo experiments. Issues include effective detection and identification of cross-linked peptides from complex mixtures. While MS-cleavable cross-linkers facilitate the sequencing and identification of cross-linked peptides, enrichable cross-linkers increase their detectability by allowing their separation from non-cross-linked peptides prior to MS analysis. Although a number of cross-linkers with single functionality have been developed in recent years, an ideal reagent would incorporate both capabilities for XL-MS studies. Therefore, two new cross-linkers have been designed and prepared that incorporate an azide (azide-A-DSBSO) or alkyne (alkyne-A-DSBSO) to enable affinity purification strategies based on click chemistry. The integration of an acid cleavage site next to the enrichment handle allows easy recovery of cross-linked products during affinity purification. In addition, these sulfoxide containing cross-linking reagents possess robust MS-cleavable bonds to facilitate fast and easy identification of cross-linked peptides using MS analysis. Optimized, gram-scale syntheses of these cross-linkers have been developed and the azide-A-DSBSO cross-linker has been evaluated with peptides and proteins to demonstrate its utility in XL-MS analysis.

METALLATION DES CHLOROSILANES PAR LES TRIALKYLSTANNYLANIONS

The stereochemistry of chlorosilane metallation by stannyl anions of the silacyclopentane series has been studied.Poor stereoselectivity is often observed for this reaction and the expected stannylsilanes are usually contaminated with products of side reactions.Concerning the mechanisms implied in the stannylation reaction, we consider that a reasonable interpretation of the experimental facts is the possibility of two competing processes: nucleophilic SN2 substitution (inversion at Si) and halogen-metal exchange (which implies retention or epimerization at the Si atom).

Direct conversion of bromohydrins to ketones

The direct conversion of halohydrins to ketones can be achieved by irradiation in benzene or toluene in the presence of small amounts of p-toluenesulfonic acid. A two step conversion of terminal alkenes to methylketones is thus achieved with good yields and inexpensive reagents.

Radical dehydroxylative alkylation of tertiary alcohols by Ti catalysis

Deoxygenative radical C?C bond-forming reactions of alcohols are a long-standing challenge in synthetic chemistry, and the current methods rely on multistep procedures. Herein, we report a direct dehydroxylative radical alkylation reaction of tertiary alcohols. This new protocol shows the feasibility of generating tertiary carbon radicals from alcohols and offers an approach for the facile and precise construction of all-carbon quaternary centers. The reaction proceeds with a broad substrate scope of alcohols and activated alkenes. It can tolerate a wide range of electrophilic coupling partners, including allylic carboxylates, aryl and vinyl electrophiles, and primary alkyl chlorides/bromides, making the method complementary to the cross-coupling procedures. The method is highly selective for the alkylation of tertiary alcohols, leaving secondary/primary alcohols (benzyl alcohols included) and phenols intact. The synthetic utility of the method is highlighted by its 10-g-scale reaction and the late-stage modification of complex molecules. A combination of experiments and density functional theory calculations establishes a plausible mechanism implicating a tertiary carbon radical generated via Ti-catalyzed homolysis of the C?OH bond.

A Modular and Diastereoselective 5 + 1 Cyclization Approach to N-(Hetero)Aryl Piperidines

A new general de novo synthesis of pharmaceutically important N-(hetero)aryl piperidines is reported. This protocol uses a robustly diastereoselective reductive amination/aza-Michael reaction sequence to achieve rapid construction of complex polysubstituted ring systems starting from widely available heterocyclic amine nucleophiles and carbonyl electrophiles. Notably, the diastereoselectivity of this process is enhanced by the presence of water, and DFT calculations support a stereochemical model involving a facially selective protonation of a water-coordinated enol intermediate.

Palladium/Copper-catalyzed Oxidation of Aliphatic Terminal Alkenes to Aldehydes Assisted by p-Benzoquinone

The development of an anti-Markovnikov Wacker-type oxidation for simple aliphatic alkenes is a significant challenge. Herein, a variety of aldehydes can be selectively obtained from various unbiased aliphatic terminal alkenes using PdCl2(MeCN)2/CuCl in the presence of p-benzoquinone (BQ) under mild reaction conditions. Isomerization of the terminal alkene to the internal alkene was suppressed via slow addition of the starting material to the reaction mixture. In addition to the Pd catalyst, CuCl and BQ were essential in order to obtain the anti-Markovnikov product with high selectivity. Terminal alkenes bearing a halogen substituent afforded their corresponding aldehydes with high anti-Markovnikov selectivity. The halogen acts as a directing group in the reaction. DFT calculations indicate that a μ-chloro Pd(II)?Cu(I) bimetallic species with BQ coordinated to Cu is the catalytically active species in the case of a terminal alkene without a directing group.

Palladium-Catalyzed Aerobic Anti-Markovnikov Oxidation of Aliphatic Alkenes to Terminal Acetals

Terminal acetals were selectively synthesized from various unbiased aliphatic terminal alkenes and 1,2-, 1,3-, or 1,4-diols using a PdCl2(MeCN)2/CuCl catalyst system in the presence of p-toluquinone under 1 atm of O2 and mild reaction conditions. The slow addition of terminal alkenes suppressed the isomerization to internal alkenes successfully. Electron-deficient cyclic alkenes, such as p-toluquinone, were key additives to enhance the catalytic activity and the anti-Markovnikov selectivity. The halogen groups in the alkenes were found to operate as directing groups, suppressing isomerization and increasing the selectivity efficiently.

Asymmetric Reductive Carbocyclization Using Engineered Ene Reductases

Ene reductases from the Old Yellow Enzyme (OYE) family reduce the C=C double bond in α,β-unsaturated compounds bearing an electron-withdrawing group, for example, a carbonyl group. This asymmetric reduction has been exploited for biocatalysis. Going beyond its canonical function, we show that members of this enzyme family can also catalyze the formation of C?C bonds. α,β-Unsaturated aldehydes and ketones containing an additional electrophilic group undergo reductive cyclization. Mechanistically, the two-electron-reduced enzyme cofactor FMN delivers a hydride to generate an enolate intermediate, which reacts with the internal electrophile. Single-site replacement of a crucial Tyr residue with a non-protic Phe or Trp favored the cyclization over the natural reduction reaction. The new transformation enabled the enantioselective synthesis of chiral cyclopropanes in up to >99 % ee.

Hydrogen Borrowing Catalysis with Secondary Alcohols: A New Route for the Generation of β-Branched Carbonyl Compounds

A hydrogen borrowing reaction employing secondary alcohols and Ph? (Me5C6) ketones to give β-branched carbonyl products is described (21 examples). This new C-C bond forming process requires low loadings of [Cp?IrCl2]2, relatively low temperatures, and up to 2.0 equiv of the secondary alcohol. Substrate-induced diastereoselectivity was observed, and this represents the first example of a diastereoselective enolate hydrogen borrowing alkylation. By utilizing the Ph? group, the β-branched products could be straightforwardly cleaved to the corresponding esters or amides using a retro-Friedel-Crafts reaction. Finally, this protocol was applied to the synthesis of fragrance compound (±)-3-methyl-5-phenylpentanol.