24070-52-8

Usage

Uses

Used in Pharmaceutical Industry:
4-bromobutyrophenone is used as an intermediate for the synthesis of various pharmaceuticals, contributing to the development of new drugs and medications.
Used in Agrochemical Industry:
4-bromobutyrophenone is used as an intermediate in the production of agrochemicals, aiding in the creation of effective pesticides and other agricultural chemicals.
Used in Organic Synthesis:
4-bromobutyrophenone is used as a building block in the manufacture of various organic compounds, playing a crucial role in the synthesis of a wide range of chemical products.
Used as a Reagent:
4-bromobutyrophenone is used as a reagent in organic synthesis, facilitating various chemical reactions and processes in research and industrial applications.
It is important to handle 4-bromobutyrophenone with care, as it is a potential irritant to the skin, eyes, and respiratory system, and may have harmful effects if ingested or inhaled.

InChI:InChI=1/C10H11BrO/c11-8-4-7-10(12)9-5-2-1-3-6-9/h1-3,5-6H,4,7-8H2

Upstream product

• 21034-21-9 α-benzoyl-γ-butyrolactone 
• 3481-02-5 cyclopropyl phenyl ketone 
• 79172-43-3 1-benzoylcyclopropanecarboxylic acid 
• 5332-06-9 4-bromobutanenitrile 
• 927-58-2 4-bromobutyroyl chloride 
• 71-43-2 benzene 
• 56489-06-6 4-bromobutyryl bromide 
• 10035-10-6 hydrogen bromide 
• 64-19-7 acetic acid 
• 935-64-8 1-phenyl-1-cyclobutanol 
• 13633-25-5 1-Bromo-4-phenylbutane 
• 1501-05-9 5-oxo-5-phenylvaleric acid 
• 100-58-3 phenylmagnesium bromide 
• 591-51-5 phenyllithium 

Downstream Products

• 100388-04-3 2-(3-bromo-propyl)-2-phenyl-[1,3]dioxolane 
• 4170-67-6 1-methyl-5-phenyl-2,3-dihydro-pyrrole 
• 3481-02-5 cyclopropyl phenyl ketone 
• 343810-59-3 4-[8-fluoro-5-(4-fluoro-phenyl)-1,3,4,5-tetrahydro-pyrido[4,3-b]indol-2-yl]-1-phenyl-butan-1-one 
• 6008-36-2 1-phenylnonan-1-one 
• 40131-79-1 4-ethyl-8-(4-oxo-4-phenyl-butyl)-1-oxa-3,8-diaza-spiro[4.5]decan-2-one 
• 858789-45-4 1,8-dibromo-4,5-diphenyl-octane-4,5-diol 
• 6072-57-7 3-methylindanone 
• 151091-46-2 VUF 4592 
• 1501-05-9 5-oxo-5-phenylvaleric acid 
• 42330-80-3 4-(p-methylphenylthio)-1-phenylbutan-1-ol 
• 82777-36-4 Picrateethyl-(4-methoxy-phenyl)-(4-oxo-4-phenyl-butyl)-sulfonium; 
• 495-40-9 propiophenone 
• 42330-79-0 3-(4-methylphenylthio)propyl phenyl ketone 

Relevant academic research and scientific papers

Transition-Metal-Free Ring-Opening Reaction of 2-Halocyclobutanols through Ring Contraction

The present work describes the preparation of halohydrins from 2-halocyclobutanones by means of reactions with Grignard reagents at ?78 °C. We discovered that the prepared cyclobutanols underwent a thermal ring-opening reaction. Depending on the structure of the starting cyclobutanol, different products were formed. More specifically, 1-substituted 2-bromocyclobutan-1-ol was found to open to γ-substituted butyrophenones. A novel 1,3-dihydro-2H-inden-2-ylidene derivative was obtained for indene-derived cyclobutanols. Based on the outcomes of the performed experiments, a mechanism for the ring-opening of cyclobutanols can be proposed.

Addition of benzyl ethers to alkynes: A metal-free synthesis of 1: H -isochromenes

Bromotrimethylsilane (TMSBr)-promoted intramolecular cyclization of (o-arylethynyl)benzyl ethers to form 1H-isochromenes at room temperature is reported. Further studies indicated that vinyl carbocations are the reaction intermediates which are stabilized by the conjugated aryl groups. Thus, O-addition of benzyl ethers/tetrahydropyrans to alkynes was achieved under metal-free, acidic conditions. These reaction conditions were compatible with an alkynyl Prins reaction; therefore, 1H-isochromenes were produced directly from alkynyl benzaldehydes and alkynyl alcohols using a one-pot procedure. This journal is

Intramolecular Cyclization of Brominated Oxime Ether Promoted with Ytterbium(0) to the Synthesis of Cyclic Imines

The first utility of ytterbium(0) as a mediating-metal in the intramolecular cyclization of brominated oxime ether was reported in this paper. In contrast to the prior methods, the N–O bond was used as a receptor of nucleophilic reagent, rather than as a source of N-centered radicals. Cyclic imines were obtained in this one-pot reaction with a broad scope of substrates and feasible reaction conditions.

Boron tribromide as a reagent for anti-Markovnikov addition of HBr to cyclopropanes

Although radical formation from a trialkylborane is well documented, the analogous reaction mode is unknown for trihaloboranes. We have discovered the generation of bromine radicals from boron tribromide and simple proton sources, such as water ortert-butanol, under open-flask conditions. Cyclopropanes bearing a variety of substituents were hydro- and deuterio-brominated to furnish anti-Markovnikov products in a highly regioselective fashion. NMR mechanistic studies and DFT calculations point to a radical pathway instead of the conventional ionic mechanism expected for BBr3

Iminyl Radicals by Reductive Cleavage of N-O Bond in Oxime Ether Promoted by SmI2: A Straightforward Synthesis of Five-Membered Cyclic Imines

A new generation method of N-centered radicals from the reductive cleavage of the N-O bond in oxime ether promoted by SmI2 is reported for the first time. The in-situ-generated N-centered radicals underwent intramolecular cyclization to afford five-membered cyclic imines in two manners: N-centered radical addition and N-centered anion nucleophilic substitution. From a synthetic point of view, an efficient synthetic method of five-membered cyclic imines was developed. A mechanism of the transformation was proposed.

Visible-light-enhanced ring opening of cycloalkanols enabled by br?nsted base-tethered acyloxy radical induced hydrogen atom transfer-electron transfer

A metal-free ring opening/halogenation of cycloalkanols, which combines both PPO/TBAX oxidant system and blue LEDs irradiation, is presented. This method produces diverse γ, α, and even more remotely halogenated ketones in moderate to excellent yields under mild conditions. Interestingly, experimental and computational studies demonstrate the novel ring size-dependent concerted/stepwise (four-/five- to eight-membered rings) hydrogen atom transfer-electron transfer induced by Br?nsted base-tethered acyloxy radical, which indicates distinct advantages brought by the cyclic structure of diacyl peroxides.

Halide and preparation method thereof, composition for preparing halide and halogenating reaction

The invention provides a halide for a halogenating reaction. The halide is used for providing a halogen in the halogenating reaction, the halide comprises any one of compounds shown in a formula I ora formula II or a formula III, in the formula I or the formula II or the formula III, the R group comprises any one of hydrogen or the halogen or an alkyl group or an aryl group or a nitro group, X comprises any one of F or Cl or Br or I, and M comprises any one of tetra-allkylammonium cation, Li, Na, K, Rb and Cs. The invention further provides a preparation method of the halide, a composition for preparing the halide and the halogenating reaction. Accordingly, normal-temperature and additive-free halogenation on the compounds can be achieved, and then products high in yieldand chemoselectivity are obtained; due to the fact that by-products generated after the halide is subjected to a corresponding reaction is likely to be dissolved into water, the corresponding products are likely to be separated and purified.

PROCESS FOR THE PREPARATION OF ORGANIC BROMIDES

The present invention provides a process for the preparation of organic bromides, by a radical bromodecarboxylation of carboxylic acids with a bromoisocyanurate.

Enhanced structural variety of nonplanar N-oxyl radical catalysts and their application to the aerobic oxidation of benzylic C-H bonds

The design and synthesis of structurally variable, nonplanar N-oxyl radical catalysts and their application to the aerobic oxidation, etherification, and acetoamidation of benzylic C-H bonds are described. The catalytic oxidation of C-H bonds represents a powerful tool to synthesize oxygenated functional molecules from simple hydrocarbons in a straightforward way. Electron-deficient N-oxyl radical catalysts, such as phthalimidoyl N-oxyl (PINO) radical, generated from N-hydroxyphthalimide (1), have attracted much attention because of their applications in the oxidation of C-H bonds with high bond dissociation energy (BDE). However, a few sites in 1 are available for structural modifications and improvements of the catalytic performance. By replacing one carbonyl group in 1 with a trifluoromethyl (CF3)-substituted sp3-carbon, we generated an additional tunable site and a nonplanar backbone, while retaining the desirable electron-withdrawing properties and increasing the lipophilicity with respect to 1. We synthesized a variety of N-hydroxy pre catalysts containing such a CF3 moiety, and investigated their utility in the aerobic oxidation of benzylic C-H bonds. Precatalysts with electron-withdrawing substituents, such as trifluoroethoxy and the acetophenone moieties, afforded higher yields than a corresponding methoxy-substituted analogue. The introduction of substituents at the aromatic ring was also effective, as evident from the performance of 7-CF3 and 4,5,6,7-tetrafluoro precatalysts. Especially the combination of trifluoroethoxy- and 4,5,6,7-tetrafluoro substitution afforded a superior performance. These catalyst systems exhibited high functional group tolerance during the aerobic oxidation of C-H bonds, and benzylic etherification and Ritter-type reactions could be carried out at room temperature when a selected precatalyst and N-bromosuccinimide (NBS) were used.

Synthesis of γ-halogenated ketones via the Ce(IV)-mediated oxidative coupling of cyclobutanols and inorganic halides

A straightforward method for the synthesis of γ-halo-substituted ketones formed via the CAN-initiated oxidative addition of halides to 1-substituted cyclobutanols has been developed. This method has short reaction times, and provides access to a range of bromo and iodo γ-substituted ketones in good to excellent yields.