53946-87-5

Usage

Uses

Used in Scientific Research:
w-Bromo-4-Hydroxyacetophenone is used as a reactant in various chemical reactions, contributing to the advancement of organic chemistry. Its unique structure allows it to participate in a range of reactions, making it a valuable compound for researchers in the field.
Used in Organic Chemistry:
w-Bromo-4-Hydroxyacetophenone is employed as a key intermediate in the synthesis of more complex organic molecules. Its bromine and hydroxyacetophenone functional groups enable it to undergo a variety of reactions, such as substitution, addition, and elimination, which are crucial for the development of new compounds and materials.
Used in Chemical Synthesis:
w-Bromo-4-Hydroxyacetophenone is used as a building block in the preparation of pharmaceuticals, agrochemicals, and other specialty chemicals. Its reactivity and versatility make it an essential component in the synthesis of a wide array of chemical products, enhancing the efficiency and effectiveness of these processes.
Used in Material Science:
w-Bromo-4-Hydroxyacetophenone is utilized in the development of new materials with specific properties, such as improved thermal stability, enhanced reactivity, or tailored electronic characteristics. Its incorporation into these materials can lead to innovative applications in various industries, including electronics, automotive, and aerospace.

InChI:InChI=1/C9H9BrO2/c1-6(10)9(12)7-2-4-8(11)5-3-7/h2-6,11H,1H3

Upstream product

• 42710-26-9 phenyl 2-bromopropionate 
• 563-76-8 α-bromopropionyl bromide 
• 108-95-2 phenol 
• 70-70-2 4-hydroxypropiophenone 

Downstream Products

• 87429-89-8 2-(4-diphenylmethylpiperazinyl)-1-(4-hydroxyphenyl)propanone 
• 70-70-2 4-hydroxypropiophenone 
• 60041-21-6 1-[1-Methyl-2-(4-hydroxy)phenyl-2-oxoethyl]-4-benzamidopiperidine 
• 23210-56-2 (+/-)-Erythro-Ifenprodil 
• 23210-56-2 (+/-)-Threo-Ifenprodil 
• 74991-32-5 (RS)-2-(4-benzylpiperidin-1-yl)-1-(4-hydroxyphenyl)propan-1-one 
• 93035-39-3 3-bromo-1-(4-hydroxyphenyl) propan-1-one 
• 1069136-75-9 4-[1-(2,4-dichlorophenyl)-3-methyl-4-oxo-5-piperidin-1-yl-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridin-2-yl]phenylpropane-1-sulfonate 
• 1069136-76-0 2-(4-butoxyphenyl)-1-(2,4-dichlorophenyl)-3-methyl-5-piperidin-1-yl-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one 
• 1001018-36-5 4-[(2,4-dichlorophenyl)amino]-3-{2-[4-(1-ethoxyethoxy)phenyl]-1-methyl-2-oxoethyl}-1-piperidin-1-yl-5,6-dihydropyridin-2(1H)-one 
• 932739-13-4 1-(2,4-dichlorophenyl)-2-(4-hydroxyphenyl)-3-methyl-5-piperidin-1-yl-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one 

Relevant academic research and scientific papers

Ifenprodil Stereoisomers: Synthesis, Absolute Configuration, and Correlation with Biological Activity

Ifenprodil (1) is a potent GluN2B-selective N-methyl-d-aspartate (NMDA) receptor antagonist that is used as a cerebral vasodilator and has been examined in clinical trials for the treatment of drug addiction, idiopathic pulmonary fibrosis, and COVID-19. To correlate biological data with configuration, all four ifenprodil stereoisomers were prepared by diastereoselective reduction and subsequent separation of enantiomers by chiral HPLC. The absolute configuration of ifenprodil stereoisomers was determined by X-ray crystal structure analysis of (1R,2S)-1a and (1S,2S)-1d. GluN2B affinity, ion channel inhibitory activity, and selectivity over α, σ, and 5-HT receptors were evaluated. (1R,2R)-Ifenprodil ((1R,2R)-1c) showed the highest affinity toward GluN2B-NMDA receptors (Ki = 5.8 nM) and high inhibition of ion flux in two-electrode voltage clamp experiments (IC50 = 223 nM). Whereas the configuration did not influence considerably the GluN2B-NMDA receptor binding, (1R)-configuration is crucial for elevated inhibitory activity. (1R,2R)-Configured ifenprodil (1R,2R)-1c exhibited high selectivity for GluN2B-NMDA receptors over adrenergic, serotonergic, and σ1 receptors.

Synthesis and preliminary photopolymerization evaluation of novel photoinitiators containing phototrigger to overcome oxygen inhibition in the UV- curing system

In this work, two types of novel photoinitiaors containing phototrigger were prepared to overcome oxygen inhibition in the UV- curing system in the absence of hydrogen donor. The structures of prepared novel photoinitiators were determined by nuclear magnetic resonance (NMR) and high resolution MS (HR[sbnd]MS) spectra data. The photo chemical behavior and photo-reactivity were also evaluated by ultraviolet-visible (UV–vis) spectroscopy and real-time Fourier transform infrared spectroscopy (RT-FTIR), respectively. The results show the prepared photoinitiators exhibit remarkable redshift compared to the commercial BP (benzophenone) and Irgacure 907 (2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one), fast photolysis by C[sbnd]S bond, good photo initiation and significant overcoming oxygen inhibition for some compounds, which can be used as one-component photoinitiator candidates.

Design, synthesis and broad-spectrum Bcr-Abl inhibitory activity of novel thiazolamide-benzamide derivatives

Bcr-Abl plays an important role in the pathogenesis and development of chronic myeloid leukemia (CML). But Bcr-Abl is prone to mutation, so it increases the difficulty of clinical treatment. Therefore, it is crucial to design a new class of broad-spectrum Bcr-Abl inhibitors. Herein, forty novel thiazolamide-benzamide derivatives were synthesized and evaluated their broad-spectrum Bcr-Abl inhibitory activities. The newly synthesized compounds were characterized by using spectrum data (1H NMR, APCI-MS and IR) and elemental analysis. The protein kinase results indicated that eight compounds (3a, 3e, 3m, 3n, 3p, 4c, 4f, 4g) showed high activities to wild-type and T315I mutation. The most potent compound 3m exhibited an Abl IC50 value as low as 1.273 μM and showed inhibition to the T315I mutant with IC50 value 39.89 μM. 3m could prove to be a new promising lead compound for the further development of broad-spectrum Bcr-Abl inhibitors to overcome clinical acquired resistance.

Synthesis of α,β-dibromo ketones by photolysis of α-bromo ketones with N-bromosuccinimide: Photoinduced β-bromination of α-bromo ketones

Irradiation of α-bromopropiophenones in the presence of NBS results in the formation of α,β-dibromopropiophenones, which can be viewed as β-bromination of α-bromopropiophenones. The reaction is believed to go through a series of reactions; photoinduced C–Br bond cleavage, elimination of HBr to give α,β-unsaturated ketone intermediates, and addition of Br2, which are formed by the reaction between HBr and NBS. From mechanistic studies of the reaction, we have also found a very convenient method for α-debromination of the α,β-dibromopropiophenones which is by simple irradiation of the dibromo ketones in acetone or 2-propanol without the use of any additives. Our results demonstrate that bromine can be added into or eliminated from the alpha, beta, or both positions to the carbonyl group by photochemical methods, which make synthetic options of bromine containing carbonyl compounds versatile.

Solvent free, light induced 1,2-bromine shift reaction of α-bromo ketones

Photolysis of α-bromopropiophenones in acetonitrile results in formation of β-bromopropiophenones with good product selectivity, which can be coined as 1,2-Br shift reaction. The product selectivity increases when the reaction is done in neat or solid state, where only the 1,2-Br shift product is formed in some cases. The reaction is suggested to proceed by C–Br bond homolysis to give a radical pair, followed by disproportionation and conjugate addition of HBr to the α,β-unsaturated ketone intermediate. When the unsaturated intermediate is stabilized by an extra conjugation, the reaction stops at the stage, in which the unsaturated ketone becomes a major product. The synthetic method described in this research fits in a category of eco-friendly organic synthesis nicely since the reaction does not use volatile organic solvents and any other additives such as acid, base or metal catalysts, etc. Besides, the method fits into perfect atom economy, which does not give any side products. The synthetic method should find much advantage over other alternative methods to obtain β-bromo carbonyl compounds.

SELECTIVE OCTAHYDRO-CYCLOPENTA[C] PYRROLE NEGATIVE MODULATORS OF NR2B

Compounds that selectively negatively modulate NMDA receptors containing an NR1/NR2B subunit, pharmaceutical compositions comprising the compounds, and methods of treating a disease using the compounds are disclosed. Such diseases include, without limitation, neurological dysfunction such as Parkinson's disease, Huntington's disease, amyotrophic lateral sclerosis, multiple sclerosis, and seizure disorders; emotional disorders; depression; bipolar disorder; obsessive-compulsive disorder; and other anxiety disorders.

NOVEL COMPOUND HAVING AFFINITY FOR AMYLOID

A compound effective as a probe targeting amyloid for image diagnosis and a reagent comprising the compound for detecting amyloid deposited on a biological tissue are provided. Provided are a compound represented by the following formula (1): wherein R1 is a group selected from the group consisting of a halogen substituent, alkyl substituent with 1 to 4 carbon atoms, alkoxy substituent having alkyl chain with 1 to 4 carbon atoms and hydroxyl group, R2 is a group selected from the group consisting of a cyano substituent, alkyl substituent with 1 to 4 carbon atoms and halogen substituent, is a group selected from the group consisting of a hydroxyl group, halogen substituent and substituent represented by the following formula: (wherein R4 is a hydrogen, halogen substituent or hydroxyl group, and m is an integer of 1 to 4), provided that a t least one of R1, R2, R3 and R4 represents a radioactive halogen, and a reagent comprising the same.

THERAPEUTIC AGENTS

Certain 4, 5, 6, 7 -tetrahydropyrrolo[3,2-c]pyridin-4-one and 4, 5 -dihydropyrrolo[3,2-c]pyridin-4-one compounds of formula (I), processes for preparing such compounds, their use in the treatment of obesity, psychiatric and neurological disorders, methods

BENZYLAMINE DERIVATIVES, METHOD FOR OPTICAL RESOLUTION OF BENZYLAMINE DERIVATIVES, PROCESS FOR PRODUCTION OF BENZYLAMINE DERIVATIVES, PROCESS FOR PRODUCTION OF OPTICALLY ACTIVE BENZYLAMINE DERIVATIVES, AND PROCESS FOR PRODUCTION OF (1R, 2S)-2-AMINO-1-(4-HYDROXYPHENYL)PROPAN-1-OL

Benzylamine derivatives having structures represented by the general formula (1): (1) a method for the optical resolution of benzylamine derivatives which comprises using optically active mandelic acid as the reagent for optical resolution; and a process for the production of optically active benzylamine derivatives which comprises the optical resolution step of precipitating an optically active (S)-benzylamine derivative represented by the general formula (3) as a salt thereof with (S)-mandelic acid in a solution containing the corresponding benzylamine derivative of the general formula (1) and (S)-mandelic acid: (3) wherein Ar is aryl of 6 to 15 carbon atoms which may be substituted; and *1 represents an asymmetric carbon atom.

Pyrrole derivatives and medicinal composition

The invention relates to a pharmaceutical composition comprising a pyrrole derivative of the following formula [1] or a pharmaceutically acceptable salt thereof, or a solvate of either of them, as an active ingredient. STR1 (wherein R1 represents hydrogen or alkoxycar91 bonylamino, R2 represents alkyl, aryl which may be substituted, aromatic heterocyclyl which may be substituted, unsubstituted amino, monoalkylamino, dialkylamino, or cyclic amino which may be substituted; R3 represents cyano or carbamoyl; R4 represents hydrogen or alkyl; E represents alkylene; q is equal to 0 or 1, A represents methyl, aryl which may be substituted, or aromatic heterocyclyl which may be substituted). The pharmaceutical composition of the invention is effective for the treatment of pollakiuria or urinary incontinence.