3884-71-7

Basic information

• Product Name: 5-BROMO-PENTAN-2-ONE
• Synonyms: 5-BROMO-PENTAN-2-ONE;3-bromopropyl methyl ketone;5-BROMO-2-PENTANONE;1-broMopentan-4-one;2-Pentanone, 5-bromo-
• CAS NO: 3884-71-7
• Molecular Formula: C₅H₉BrO
• Molecular Weight: 165.02836
• EINECS: 223-419-2
• Mol File: 3884-71-7.mol
• Article Data: 42

Chemical Properties

• Boiling Point: 190.6°Cat760mmHg
• Flash Point: 76.1°C
• Appearance: /
• Density: 1.359g/cm³
• Vapor Pressure: 0.537mmHg at 25°C
• Refractive Index: 1.455
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• CAS DataBase Reference: 5-BROMO-PENTAN-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-BROMO-PENTAN-2-ONE(3884-71-7)
• EPA Substance Registry System: 5-BROMO-PENTAN-2-ONE(3884-71-7)

Safety Data

• Hazardous Substances Data: 3884-71-7(Hazardous Substances Data)

Usage

General Description

5-Bromo-pentan-2-one is a chemical compound with the molecular formula C5H9BrO. It is derived from pentan-2-one, with a bromine atom substituted at the 5th carbon position. 5-BROMO-PENTAN-2-ONE is commonly used in organic synthesis as a building block for the production of various pharmaceuticals, agrochemicals, and other advanced materials. It is also a key intermediate in the manufacture of fine chemicals and active pharmaceutical ingredients. 5-Bromo-pentan-2-one has a wide range of applications and is utilized in the fields of medicinal chemistry, chemical research, and chemical manufacturing. Additionally, it poses certain hazards and precautions should be taken while handling and storing this compound.

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

Upstream product

• 5891-21-4 5-chloro-2-pentanone 
• 29021-98-5 3-(2-methyl-[1,3]dioxolan-2-yl)-propan-1-ol 
• 20117-47-9 1-methylcyclobutanol 
• 1119-51-3 bromopentene 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 34764-77-7 methyl 3-bromo-1-propenyl ketone 
• 5390-04-5 pent-1-yn-5-ol 
• 111-24-0 1,5-dibromo-pentane 
• 123-76-2 levulinic acid 
• 1115-30-6 diethyl acetylsuccinate 
• 4388-57-2 tert-butyldimethylsilyl 3-(2-methyl-1,3-dioxolan-2-yl)propanoate 
• 765-43-5 Cyclopropyl methyl ketone 
• 10035-10-6 hydrogen bromide 
• 146580-95-2 5-Bromo-1-diazopentan-2-one 

Downstream Products

• 19679-75-5 cyano-2 methyl-2 tetrahydrofuranne 
• 16538-91-3 decane-2,9-dione 
• 81358-55-6 5-(phenylsulfenyl)-2-pentanone 
• 89534-22-5 5-methylsulfanyl-pentan-2-one 
• 861077-19-2 5-anilino-pentan-2-one 
• 105-14-6 5-diethylamino-2-pentanone 
• 98321-74-5 5-mercaptopentan-2-one 
• 765-43-5 Cyclopropyl methyl ketone 
• 872-32-2 2-methyl-1H-pyrroline 
• 691412-31-4 5-(ethyl-methyl-amino)-pentan-2-one 
• 22020-87-7 5-nitro-2-pentanone 
• 1602829-85-5 1-methyl-4,4-bis(phenylsulfonyl)-2-vinylidenecycloheptanol 
• 1602829-52-6 10-bromo-6,6-bis(phenylsulfonyl)dec-8-yn-2-one 
• 6077-73-2 <4-Methyl-6-aethoxycarbonyl-penten-(4)-yl>-triphenylphosphoniumbromid 

Relevant articles and documents

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.

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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.

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.