4981-64-0

Usage

Uses

Used in Pharmaceutical Industry:
4'-Bromobutyrophenone is used as a precursor in the synthesis of various medications, contributing to the development of new drugs and therapeutic agents.
Used in Agrochemical Industry:
It is utilized as an intermediate in the manufacturing of agrochemicals, playing a crucial role in the production of pesticides and other agricultural chemicals to protect crops and enhance agricultural productivity.
Used in Fine Chemicals Industry:
4'-Bromobutyrophenone is employed in the production of other fine chemicals, which are high-purity, specialty chemicals used in various applications, including research, pharmaceuticals, and other industries.
Safety Precautions:
Due to its potential hazards, such as skin and eye irritation, and its harmful effects if ingested or inhaled, 4'-Bromobutyrophenone should be handled and stored with care. Appropriate safety measures and regulations must be followed to ensure the safety of workers and the environment.

InChI:InChI=1/C10H11BrO/c1-2-3-10(12)8-4-6-9(11)7-5-8/h4-7H,2-3H2,1H3

Upstream product

• 106-31-0 butanoic acid anhydride 
• 108-86-1 bromobenzene 
• 201230-82-2 carbon monoxide 
• 589-87-7 1,4-bromoiodobenzene 
• 107-08-4 1-iodo-propane 
• 141-75-3 butyryl chloride 
• 41492-05-1 p-bromobutylbenzene 
• 623-00-7 4-bromobenzenecarbonitrile 
• 2234-82-4 1-propylmagnesium chloride 
• 586-75-4 4-chlorobenzoyl chloride 
• 109480-78-6 N-methoxy-N-methylbutanamide 
• 18620-02-5 (4-bromophenyl)magnesium bromide 
• 5467-74-3 4-Bromophenylboronic acid 
• 632336-93-7 2-bromo-1-(4-bromophenyl)butan-1-one 

Downstream Products

• 38847-68-6 1-(4-bromo-phenyl)-butane-1,2-dione-2-oxime 
• 41492-05-1 p-bromobutylbenzene 
• 146781-56-8 p-Brom-α-propyl-benzylamin 
• 91715-78-5 4-Brom-3-nitrophenyl)-propylketon 
• 495-40-9 propiophenone 
• 875433-12-8 3-(4-bromo-benzoyl)-pentanoic acid ethyl ester 
• 927190-95-2 3-[4-(3-benzyloxy-prop-1-ynyl)-benzoyl]-pentanoic acid ethyl ester 
• 343564-19-2 1-(4-bromophenyl)-2-ethyl-4,4,4-trifluoro-1,3-butanedione 
• 1426663-59-3 5-ethyl-6-[4-(hexahydropyrrolo[3,4-b][1.4]oxazin-6(2H)-yl)phenyl]-2-oxo-1,2-dihydropyridine-3-carboxylic acid hydrochloride 
• 1426670-44-1 N-(1-(4-bromophenyl)butylidene)-1-(2,4-dimethoxyphenyl)methanamine 
• 1426669-56-8 methyl-6-(4-bromophenyl)-1-(2,4-dimethoxybenzyl)-5-ethyl-2-oxo-1,2-dihydropyridine-3-carboxylate 
• 1426669-58-0 6-(4-bromophenyl)-1-(2,4-dimethoxybenzyl)-5-ethyl-2-oxo-1,2-dihydropyridine-3-carboxylic acid 

Relevant academic research and scientific papers

Selective electrochemical oxidation of aromatic hydrocarbons and preparation of mono/multi-carbonyl compounds

A selective electrochemical oxidation was developed under mild condition. Various mono-carbonyl and multi-carbonyl compounds can be prepared from different aromatic hydrocarbons with moderate to excellent yield and selectivity by virtue of this electrochemical oxidation. The produced carbonyl compounds can be further transformed into α-ketoamides, homoallylic alcohols and oximes in a one-pot reaction. In particular, a series of α-ketoamides were prepared in a one-pot continuous electrolysis. Mechanistic studies showed that 2,2,2-trifluoroethan-1-ol (TFE) can interact with catalyst species and generate the corresponding hydrogen-bonding complex to enhance the electrochemical oxidation performance. [Figure not available: see fulltext.]

Intramolecular N?H???F Hydrogen Bonding Interaction in a Series of 4-Anilino-5-Fluoroquinazolines: Experimental and Theoretical Characterization of Electronic and Conformational Effects

The 4-anilino-6,7-ethylenedioxy-5-fluoroquinazoline scaffold is presented as a novel model system for the characterization of the weak NH???F hydrogen bonding (HB) interaction. In this scaffold, the aniline NH proton is forced into close proximity with the nearby fluorine (dH,F～2.0 ?, ∠～138°), and a through-space interaction is observed by NMR spectroscopy with couplings (1hJNH,F) of 19±1 Hz. A combination of experimental (NMR spectroscopy and X-ray crystallography) and theoretical methods (DFT calculations) were used for the characterization of this weak interaction. In particular, the effects of conformational rigidity and steric compression on coupling were investigated. This scaffold was used for the direct comparison of fluoride with methoxy as HB acceptors, and the susceptibility of the NH???F interaction to changes in electron distribution and resonance was probed by preparing a series of molecules with different electron-donating or -withdrawing groups in the positions para to the NH and F. The results support the idea that fluorine can act as a weak HB acceptor, and the HB strength can be modulated through additive and linear electronic substituent effects.

Iridium-Catalyzed Asymmetric Hydrogenation of α-Fluoro Ketones via a Dynamic Kinetic Resolution Strategy

The discrimination of a fluorine atom from a hydrogen atom has been challenging in asymmetric catalysis. We herein report iridium-catalyzed hydrogenation of α-fluoro ketones using a strategy of dynamic kinetic resolution. Both enantiomeric and diastereomeric selectivities were satisfactory in the preparation of β-fluoro alcohols. The DFT calculation revealed a C-F···Na charge-dipole interaction in the transition state of hydride transfer. This noncovalent interaction would be responsible for the diastereomeric control.

Facile preparation of 5-alkyl-1-aryltetrazoles with arenes, acyl chlorides, hydroxylamine, and diphenylphosphoryl azide

Successive treatment of arenes with acyl chlorides and AlCl3, the addition of water and removal of solvent, the reaction with NH2OH?HCl and K2CO3, and the reaction with diphenylphosphoryl azide and DBU under warming conditions gave the corresponding 5-alkyl-1-aryltetrazoles efficiently in good to moderate yields. The present method is one-pot transformation of arenes into 5-alkyl-1-aryltetrazoles using the Friedel-Crafts acylation and the Beckmann rearrangement under transition-metal-free conditions.

Catalyst-Free Photodriven Reduction of α-Haloketones with Hantzsch Ester

Catalyst-free dehalogenation of α-haloketones under visible light irradiation is studied. The reactions were carried out in common organic solvent. The outcomes of dechlorination are excellent in yields up to 92%, and it is also applicable to bromides, which give even higher yields. The reaction is tolerable to a broad spectrum of substrates, especially to aromatic ketones, including various aryl and hetaryl groups. There are two examples of aliphatic ketones presented in the paper, although their reactivities are not as high as that of the aromatic ketones.

Identification and Profiling of Hydantoins - A Novel Class of Potent Antimycobacterial DprE1 Inhibitors

Tuberculosis is the leading cause of death worldwide from infectious diseases. With the development of drug-resistant strains of Mycobacterium tuberculosis, there is an acute need for new medicines with novel modes of action. Herein, we report the discovery and profiling of a novel hydantoin-based family of antimycobacterial inhibitors of the decaprenylphospho-β-d-ribofuranose 2-oxidase (DprE1). In this study, we have prepared a library of more than a 100 compounds and evaluated them for their biological and physicochemical properties. The series is characterized by high enzymatic and whole-cell activity, low cytotoxicity, and a good overall physicochemical profile. In addition, we show that the series acts via reversible inhibition of the DprE1 enzyme. Overall, the novel compound family forms an attractive base for progression to further stages of optimization and may provide a promising drug candidate in the future.

Palladium-Catalyzed Carbonylative Coupling of Aryl Iodides with Alkyl Bromides: Efficient Synthesis of Alkyl Aryl Ketones

Alkyl aryl ketones are important structures with applications in many areas of chemistry. Hence, efficient procedures for their production are particularly attractive. In this communication, a general and efficient carbonylative cross-coupling of aryl iodides and unactivated alkyl bromides is presented. By using a simple palladium catalyst, a series of alkyl aryl ketones were synthesized in moderate to excellent yields from readily available alkyl and aryl halides in an In-Ex tube with formic acid as the CO source. In this study both primary and secondary alkyl bromides/iodides were suitable coupling partners. Additionally, this method can also be employed for the late-stage functionalization of complex natural products and polyfunctionalized molecules. (Figure presented.).

Dual oxidation/bromination of alkylbenzenes

In the presence of sodium bromide and Oxone, a range of alkylbenzene derivatives are brominated and/or oxidized with up to four C-H bonds being functionalized.

MIL-101 as reusable solid catalyst for autoxidation of benzylic hydrocarbons in the absence of additional oxidizing reagents

Materiaux de l'Institute Lavosier-101 (MIL-101) promotes benzylic oxidation of hydrocarbons exclusively by molecular oxygen in the absence of any other oxidizing reagent or initiator. Using indane as model compound, the selectivity toward the wanted ol/one mixture is higher for MIL-101(Cr) (87% selectivity at 30% conversion) than for MIL-101(Fe) (71% selectivity at 30% conversion), a fact that was associated with the preferential adsorption of indane within the pore system. Product distribution and quenching experiments with 2,2,6,6-tetramethyl-1-piperidinyloxy, benzoic acid, and dimethylformamide show that the reaction mechanism is a radical chain autoxidation of the benzylic positions by molecular oxygen, and the differences in selectivity have been attributed to the occurrence of the autoxidation process inside or outside the metal organic framework pores. MIL-101 is reusable, does not leach metals to the solution, and maintains the crystal structure during the reaction. The scope of the benzylic oxidation was expanded to other benzylic compounds including ethylbenzene, n-butylbenzene, iso-butylbenzene, 1-bromo-4-butylbenzene, sec-butylbenzene, and cumene.

ROR GAMMA (RORY) MODULATORS

The present invention relates to compounds according to Formula I: Wherein: A11 - A14 are N or CR11, CR12, CR13, CR14, respectively, with the proviso that no more than two of the four positions A can be simultaneously N; R1 is C(1-6)alkyl, C(3-6)cycloalkyl, C(3-6)cycloalkylC(1 -3)alkyl, (di)C(1-6)alkylamino, (di)C(3-6)cycloalkylamino or (di)(C(3-6)cycloalkylC(1 -3)alkyl)amino, with all carbon atoms of alkyl groups optionally substituted with one or more F and all carbon atoms of cycloalkyl groups optionally substituted with one or more F or methyl; R2 and R3 are independently H, F, methyl, ethyl, hydroxy, methoxy or R2 and R3 together is carbonyl, all alkyl groups, if present, optionally being substituted with one or more F; R4 is H or C(1-6)alkyl; R5 is H, hydroxyethyl, methoxyethyl, C(1-6)alkyl, C(6-10)aryl, C(6-10)arylC(1-3)alkyl, C(1 -9)heteroaryl, C(1-9)heteroarylC(1-3)alkyl, C(3-6)cycloalkyl, C(3-6)cycloalkylC(1 -3)alkyl, C(2-5)heterocycloalkyl or C(2-5)heterocycloalkylC(1-3)alkyl, all groups optionally substituted with one or more F, CI, C(1-2)alkyl, C(1-2)alkoxy or cyano; the sulfonyl group with R1 is represented by one of R7, R8 or R9; the remaining R6-RH are independently H, halogen, C(1-3)alkoxy, (di)C(1-3)alkylamino or C(1-6)alkyl, all of the alkyl groups optionally being substituted with one or more F; and Ri5 and Ri6 are independently H, C(1-6)alkyl, C(3-6)cycloalkyl, C(3-6)cycloalkylC(1-3)alkyl, C(6-10)aryl, C(6-10)arylC(1-3)alkyl, C(1-9)heteroaryl, C(1-9)heteroarylC(1-3)alkyl, C(2-5)heterocycloalkyl or C(2-5)heterocycloalkylC(1-3)alkyl, all groups optionally substituted with one or more F, CI, C(1-2)alkyl, C(1-2)alkoxy or cyano. The compounds can be used as inhibitors of RORy and are useful for the treatment of RORy mediated diseases.