31827-94-8

Basic information

• Product Name: 2-Bromo-4'-iodoacetophenone
• Synonyms: 4-IODOPHENACYL BROMIDE;2-BROMO-1-(4-IODO-PHENYL)-ETHANONE;2-bromo-4'-iodoacetophenone;NSC83522;2-Bromo-4'-iodoacetophenone, 2-Bromo-1-(4-iodophenyl)ethan-1-one;2-broMo-1-(4-iodophenyl)ethan-1-one;Ethanone, 2-broMo-1-(4-iodophenyl)-;4-Iodophenacylbromide97%
• CAS NO: 31827-94-8
• Molecular Formula: C₈H₆BrIO
• Molecular Weight: 324.94
• Mol File: 31827-94-8.mol

Chemical Properties

• Melting Point: 113.5 °C(Solv: ethanol, 95% (64-17-5))
• Boiling Point: 328.7 °C at 760 mmHg
• Flash Point: 152.6 °C
• Appearance: /
• Density: 2.08 g/cm³
• Storage Temp.: Keep Cold
• Sensitive: Lachrymatory
• CAS DataBase Reference: 2-Bromo-4'-iodoacetophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromo-4'-iodoacetophenone(31827-94-8)
• EPA Substance Registry System: 2-Bromo-4'-iodoacetophenone(31827-94-8)

Safety Data

• Hazard Codes: C
• Hazardous Substances Data: 31827-94-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Bromo-4'-iodoacetophenone is used as a precursor for the synthesis of pharmaceutical compounds, leveraging its unique structure and reactivity to create new drugs with potential therapeutic applications. Its ability to participate in various chemical reactions allows for the modification of existing drugs, enhancing their efficacy and targeting specific biological pathways.
Used in Chemical Industry:
In the chemical industry, 2-Bromo-4'-iodoacetophenone serves as a versatile building block for the production of a wide range of organic compounds. Its halogens can be utilized in reactions such as halogenation, substitution, and coupling, enabling the synthesis of complex molecules with diverse applications in various fields, including materials science, agrochemicals, and specialty chemicals.
Used in Research and Development:
2-Bromo-4'-iodoacetophenone is employed as a research compound in academic and industrial laboratories, where its unique properties and reactivity are explored for the development of new synthetic methods, catalysts, and reaction pathways. Its potential as a key intermediate in the synthesis of novel organic compounds makes it an important tool for advancing the field of organic chemistry and discovering new applications.

Upstream product

• 13329-40-3 4-Iodoacetophenone 
• 7726-95-6 bromine 
• 64-19-7 acetic acid 
• 186581-53-3 diazomethane 
• 619-58-9 4-iodobenzoic acid 
• 766-99-4 1-ethynyl-4-iodobenzene 
• 2351-50-0 4-iodostyrene 
• 22118-09-8 2-bromoacetyl chloride 
• 591-50-4 iodobenzene 
• 25309-64-2 4-ethyl-1-iodobenzene 

Downstream Products

• 7248-94-4 1-ethyl-1-(4-iodo-phenacyl)-piperidinium; bromide 
• 7248-92-2 1-(4-iodo-phenacyl)-pyridinium; bromide 
• 214958-27-7 2-(4-iodophenyl)imidazo[1,2-α]pyridine 
• 7508-66-9 2-chloro-1-(4-iodo-phenacyl)-pyridinium; bromide 
• 7466-75-3 2-bromo-1-(4-iodo-phenacyl)-pyridinium; bromide 
• 6267-54-5 6-chloro-1-(4-iodo-phenacyl)-quinolinium; bromide 
• 7478-19-5 8-hydroxy-1-(4-iodo-phenacyl)-quinolinium; bromide 
• 6267-57-8 1-(4-iodo-phenacyl)-1-methyl-1,2,3,4-tetrahydro-quinolinium; bromide 
• 122262-59-3 3-hydroxy-6-iodo-2-(4-iodo-phenyl)-quinoline-4-carboxylic acid 
• 122262-62-8 3-hydroxy-2-(4-iodo-phenyl)-quinoline-4-carboxylic acid 
• 90842-69-6 (2-(4-iodophenyl)-2-oxoethyl) acetate 
• 118001-66-4 6-(4-iodophenyl)imidazo[2,1-b][1,3]thiazole 
• 118001-69-7 2-(4-iodophenyl)imidazo[1,2-a]pyrimidine 
• 99582-76-0 2-(2-Imino-benzothiazol-3-yl)-1-(4-iodo-phenyl)-ethanone; hydrobromide 

Relevant articles and documents

Imidazolylacetophenone oxime-based multifunctional neuroprotective agents: Discovery and structure-activity relationships

Alzheimer's disease (AD) possesses a complex pathogenetic mechanism. Nowadays, multitarget agents are considered to have potential in effectively treating AD via triggering molecules in functionally complementary pathways at the same time. Here, based on the screening (～1400 compounds) against neuroinflammation, an imidazolylacetophenone oxime ether (IOE) was discovered as a novel hit. In order to obtain SARs, a series of imidazolylacetophenone oxime derivatives were constructed, and their C=N bonds were confirmed as the Z configuration by single crystals. These derivatives exhibited potential multifunctional neuroprotective effects including anti-neuroin?ammatory, antioxidative damage, metal-chelating, inhibition of acetylcholinesterase (AChE) properties. Among these derivatives, compound 12i displayed the most potent inhibitory activity against nitric oxide (NO) production with EC50 value of 0.57 μM 12i can dose-dependently suppress the expression of iNOS and COX-2 but not change the expression of HO-1 protein. Moreover, 12i exhibited evidently neuroprotective effects on H2O2-induced PC12 cells damage and ferroptosis without cytotoxicity at 10 μM, as well as selectively metal chelating properties via chelating Cu2+. In addition, 12i showed a mixed-type inhibitory effect on AChE in vitro. The structure-activity relationships (SARs) analysis indicated that dioxolane groups on benzene ring and rigid oxime ester can improve the activity. Parallel artificial membrane permeation assay (PAMPA) also verified that 12i can overcome the blood-brain barrier (BBB). Overall, this is the ?rst report on imidazolylacetophenone oxime-based multifunctional neuroprotective effects, suggesting that this type of compounds might be novel multifunctional agents against AD.

Redesigning of the cap conformation and symmetry of the diphenylethyne core to yield highly potent pan-genotypic NS5A inhibitors with high potency and high resistance barrier

Herein, we report the discovery of several NS5A inhibitors with potency against HCV genotype 1b in the picomolar range. Compounds (15, 33) were of extremely high potency against HCV genotype 1b (EC50 ≈ 1 pM), improved activity against genotype 3a (GT 3a) and good metabolic stability. We studied the impact of changing the cap conformation relative to the diphenylethyne core and/or compound symmetry on both potency and metabolic stability. The analogs obtained exhibited improved potency against HCV genotypes 1a, 1b, 3a and 4a compared to the clinically approved candidate daclatasvir with EC50 values in the low picomolar range and SI50s > 7 orders of magnitude. Compound 15, a symmetrically m-, m’-substituted diphenyl ethyne analog, was 150-fold more potent than daclatasvir against GT 3a, while compound 33, an asymmetrically m-, p-substituted diphenyl ethyne analog, was 35-fold more potent than daclatasvir against GT 3a. In addition, compound 15 exhibited a higher resistance barrier than daclatasvir against genotype 1b.

Synthesis and Structure-Activity Relationship of Dual-Stage Antimalarial Pyrazolo[3,4- b]pyridines

Malaria remains one of the most deadly infectious diseases, causing hundreds of thousands of deaths each year, primarily in young children and pregnant mothers. Here, we report the discovery and derivatization of a series of pyrazolo[3,4-b]pyridines targeting Plasmodium falciparum, the deadliest species of the malaria parasite. Hit compounds in this series display sub-micromolar in vitro activity against the intraerythrocytic stage of the parasite as well as little to no toxicity against the human fibroblast BJ and liver HepG2 cell lines. In addition, our hit compounds show good activity against the liver stage of the parasite but little activity against the gametocyte stage. Parasitological profiles, including rate of killing, docking, and molecular dynamics studies, suggest that our compounds may target the Qo binding site of cytochrome bc1.

2-Amino-4-arylthiazoles through One-Pot Transformation of Alkylarenes with NBS and Thioureas

Treatment of alkylarenes with N-bromosuccinimide in a mixture of ethyl acetate and water at 60 °C, a mixture of acetonitrile and water at 80 °C, or a mixture of diethyl carbonate and water under irradiation with a tungsten lamp, followed by a reaction with thioureas or arenethioamides provided the corresponding 2-amino- 4-arylthiazoles or 2,4-diarylthiazoles in good to moderate yields, respectively, in one pot. The present reaction is an efficient one-pot transformation method of alkylarenes into 2-amino-4-arylthiazoles and 2,4-diarylthiazoles directly under mild and transition-metal-free conditions.

One-Pot Preparation of Aromatic Amides, 4-Arylthiazoles, and 4-Arylimidazoles from Arenes

Simple treatment of arenes with α-bromoacetyl chloride and AlCl3, followed by the reaction with molecular iodine and aq. NH3, thioamides, or amidines gave the corresponding primary aromatic amides, 4-arylthiazoles, or 4-arylimidazoles in good yields, respectively. Aryl α-bromomethyl ketones are the key intermediates in those reactions. Primary aromatic amides were formed from arenes through the reaction of aryl α-bromomethyl ketones with molecular iodine and aq. NH3, and 4-arylthiazoles and 4-arylimidazoles were formed from arenes through the reactions of aryl α-bromomethyl ketones with thioamides and amidines, respectively, in one pot under transition-metal-free conditions.

Novel arylimino thiazole compound, preparation method and uses thereof

The present invention relates to a compound with antibacterial synergy activity, a preparation and uses thereof, particularly to a novel arylimino thiazole compound, a preparation method and uses thereof, and specifically discloses a class of compounds represented by a formula (I) or optical isomers, cis-trans isomers or pharmaceutically acceptable salts thereof, a preparation method and uses thereof. The invention further discloses a pharmaceutical composition containing the compound. The compound of the present invention can effectively enhance the antibacterial activity of antibiotics, andcan be used for treating antibiotic-resistant bacteria. The formula (I) is defined in the specification.

Antibacterial synergist, preparation method and uses thereof

The present invention relates to an antibacterial synergist, a preparation method and uses thereof, and specifically discloses a compound represented by a formula (I) and having antibacterial synergyactivity, or an optical isomer, a cis-trans isomer or a pharmaceutically acceptable salt thereof, and a preparation method thereof. The present invention further discloses a medical composition containing the compound, and uses thereof. According to the present invention, the compound can effectively enhance the antibacterial activity of polymyxin B against Acinetobacter baumannii and Klebsiella pneumoniae, and can be used for the antibacterial treatment of pathogenic bacteria insensitive to polymyxin or having low bacterial inhibition activity. The formula (I) is defined in the specification.

Selective Asymmetric Transfer Hydrogenation of α-Substituted Acetophenones with Bifunctional Oxo-Tethered Ruthenium(II) Catalysts

A practical method for the asymmetric transfer hydrogenation of α-substituted ketones was developed utilizing oxo-tethered N-sulfonyldiamine-ruthenium complexes. Reduction by HCO2H and HCO2K in a mixed solvent of EtOAc/H2O allowed for the selective synthesis of halohydrins from 2-bromoacetophenone (98%) and 2-chloroacetophenone (>99%), leading to suppressed undesired side reactions stemming from formylation under the typical reaction conditions using an azeotropic 5:2 mixture of HCO2H and Et3N. A range of functional groups, such as halogens, methoxy, nitro, dimethylamino, and ester groups, were well tolerated, highlighting the potential of this method. Nearly complete selectivity with a preferable ee was maintained even with a substrate/catalyst (S/C) ratio of 5000. This catalyst system was also effective for the asymmetric reduction of α-sulfonated ketones without eroding the leaving group. (Figure presented.).

Synthesis and biological evaluation of novel thiazole- VX-809 hybrid derivatives as F508del correctors by QSAR-based filtering tools

The most common CF mutation, F508del, impairs the processing and gating of CFTR protein. This deletion results in the improper folding of the protein and its degradation before it reaches the plasma membrane of epithelial cells. Present correctors, like VX809 only induce a partial rescue of the mutant protein. Our previous studies reported a class of compounds, called aminoarylthiazoles (AATs), featuring an interesting activity as correctors. Some of them show additive effect with VX809 indicating a different mechanism of action. In an attempt to construct more interesting molecules, it was thought to generate chemically hybrid compounds, blending a portion of VX809 merged to the thiazole scaffold. This approach was guided by the development of QSAR analyses, which were performed based on the F508del correctors so far disclosed in the literature. This strategy was aimed at exploring the key requirements turning in the corrector ability of the collected derivatives and allowed us to derive a predictive model guiding for the synthesis of novel hybrids as promising correctors. The new molecules were tested in functional and biochemical assays on bronchial CFBE41o-cells expressing F508del-CFTR showing a promising corrector activity.

Fe-Catalyzed Cycloisomerization of Aryl Allenyl Ketones: Access to 3-Arylidene-indan-1-ones

A cycloisomerization of aryl allenyl ketones to 3-arylidene-indan-1-ones using a cationic Fe-complex as a catalyst is reported. The catalyst opens a synthetically interesting reaction pathway to this surprisingly underrepresented class of indanones that are not accessible using alternative catalytic systems.