126581-65-5

Basic information

• Product Name: 2-BROMO-1-(5-FLUORO-2-HYDROXYPHENYL)ETHANONE
• Synonyms: 5-FLUORO-2-HYDROXYPHENACYL BROMIDE;2-BROMO-1-(5-FLUORO-2-HYDROXYPHENYL)ETHANONE;2-BROMO-5'-FLUORO-2'-HYDROXYACETOPHENONE;2-Bromo-1-(5-Fluoro-2-Hydroxy-Phenyl)-Ethanon
• CAS NO: 126581-65-5
• Molecular Formula: C₈H₆BrFO₂
• Molecular Weight: 233.03
• Mol File: 126581-65-5.mol

Chemical Properties

• Melting Point: 87-91 °C
• Boiling Point: 290.6 °C at 760 mmHg
• Flash Point: 129.5 °C
• Appearance: /
• Density: 1.703 g/cm³
• Vapor Pressure: 0.00118mmHg at 25°C
• Refractive Index: 1.585
• Storage Temp.: Keep Cold
• PKA: 7.50±0.43(Predicted)
• Sensitive: Lachrymatory
• CAS DataBase Reference: 2-BROMO-1-(5-FLUORO-2-HYDROXYPHENYL)ETHANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-BROMO-1-(5-FLUORO-2-HYDROXYPHENYL)ETHANONE(126581-65-5)
• EPA Substance Registry System: 2-BROMO-1-(5-FLUORO-2-HYDROXYPHENYL)ETHANONE(126581-65-5)

Safety Data

• Hazard Codes: Xn,C
• Statements: 22
• RIDADR: UN 3335
• WGK Germany: 3
• Hazardous Substances Data: 126581-65-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-BROMO-1-(5-FLUORO-2-HYDROXYPHENYL)ETHANONE is used as a synthetic intermediate for the production of various pharmaceuticals. Its unique structure, featuring a bromine and fluorine atom alongside a hydroxyl group, makes it a valuable building block in the creation of new drug molecules, potentially contributing to the development of novel treatments and therapies.
Used in Organic Synthesis:
In the field of organic chemistry, 2-BROMO-1-(5-FLUORO-2-HYDROXYPHENYL)ETHANONE serves as a key intermediate in the synthesis of a range of organic compounds. Its reactivity and the presence of multiple functional groups facilitate its involvement in numerous chemical reactions, making it a versatile component in the synthesis of specialty chemicals and other complex organic molecules.

InChI:InChI=1/C8H6BrFO2/c9-4-8(12)6-3-5(10)1-2-7(6)11/h1-3,11H,4H2

Upstream product

• 394-32-1 1-(5-fluoro-2-hydroxyphenyl)ethan-1-one 
• 459-60-9 1-fluoro-4-methoxybenzene 

Downstream Products

• 126581-64-4 α-morpholino-(2-hydroxy-5-fluoro)acetophenone 
• 1207618-58-3 ethyl 1-[4-(5-fluoro-2-hydroxyphenyl)-1,3-thiazol-2-yl]-4-piperidinecarboxylate 
• 1422718-22-6 4-fluoro-2-(imidazo[1,2-a]pyridine-2-yl)phenol 

Relevant articles and documents

MeONH 2·hCl-Mediated α-Methylenation/Conjugate Addition of α-Sulfonylo-Hydroxyacetophenones with Methyl Sulfoxides: Route to 3-Sulfonylchroman-4-ones

A novel and efficient route for the synthesis of 3-sulfonylchroman-4-ones from α-sulfonyl o -hydroxyacetophenones with methyl sulfoxides via a MeONH 2·HCl-mediated sequential methylenation/ conjugate addition is described. Plausible reaction mechanisms are proposed and discussed. Various reaction conditions for this novel, one-pot, environmentally friendly conversion were investigated.

C-H bond cleavage-enabled aerobic ring-opening reaction of: In situ formed 2-aminobenzofuran-3(2 H)-ones

A C-H bond cleavage-enabled aerobic ring-opening reaction of 2-aminobenzofuran-3(2H)-ones formed in situ by hemiacetals with a variety of amines is reported. This simple one-pot reaction provides an alternative approach to obtain o-hydroxyaryl glyoxylamides in excellent yields of up to 97%. Alkylamines react with hemiacetals via a catalyst-free dehydration condensation to generate 2-aminobenzofuran-3(2H)-ones. The in situ formed semicyclic N,O-acetals undergo the same amine-initiated C-H bond hydroxylation in air under mild conditions to afford ring-opening products. Similarly, arylamines were investigated as substrates for a two-step tandem process involving a DPP-catalyzed condensation followed by a Et2NH-mediated C-H hydroxylation. Unlike the previously reported functionalization of N,O-acetals via a C-O or C-N cleavage, the aerobic oxidative C-H hydroxylation in this reaction, which is promoted by using stoichiometric amounts of alkylamines as both a Lewis base and a reductant at room temperature under atmospheric air, proceeds via α-carbonyl-stabilized carbanion intermediates from the C-H cleavage of N,O-acetals. This journal is

PdCl2/CuCl2/Bi(OTf)3-promoted Construction of Sulfonyl Dibenzooxabicyclo[3.3.1]nonanes and Arylnaphthalenes via Intramolecular Annulation of Sulfonyl o-Allylarylchromanones

PdCl2/CuCl2/Bi(OTf)3-promoted intramolecular domino annulation of sulfonyl o-allylarylchromanones provides tetracyclic sulfonyl dibenzooxabicyclo[3.3.1]nonanes and bicyclic arylnaphthalenes with good to excellent yields in MeOH at room (25 °C) and refluxing (65 °C) temperature, respectively. The starting sulfonyl o-allylarylchromanones can be easily obtained from the intermolecular cyclocondensation of α-sulfonyl o-hydroxyacetophenones and o-allylbenzaldehydes. The uses of various catalysts and solvent systems are investigated herein for convenient transformation. A plausible mechanism is proposed and discussed. This protocol provides one-pot ring closure via carbon-carbon (C?C) bond formation. (Figure presented.).

Temperature-Controlled Desulfonylative Condensation of α-Sulfonyl o-Hydroxyacetophenones and 2-Formyl Azaarenes: Synthesis of Azaaryl Aurones and Flavones

Temperature-controlled intermolecular desulfonylative condensation of α-sulfonyl o-hydroxyacetophenones with 2-formyl azaarenes (pyridines and quinolones) provides azaaryl (pyridyl and quinolyl) aurones and flavones under warming and refluxing toluene reaction conditions via the formation of the intermediate of sulfonyl chroman-4-one. The uses of various solvents are investigated for facile and efficient transformation. A plausible mechanism is proposed.

Discovery of clinical candidate (1 R,4 r)-4-((R)-2-((S)-6-Fluoro-5 H-imidazo[5,1-A[isoindol-5-yl)-1-hydroxyethyl)cyclohexan-1-ol (Navoximod), a potent and selective inhibitor of indoleamine 2,3-dioxygenase 1

A novel class of 5-substituted 5H-imidazo[5,1-a]isoindoles are described as potent inhibitors of indoleamine 2,3-dioxygenase 1 (IDO1). A structure-based drug design approach was used to elaborate the 5H-imidazo[5,1-a]isoindole core and to improve potency and pharmacological properties. Suitably placed hydrophobic and polar functional groups in the lead molecule allowed improvement of IDO1 inhibitory activity while minimizing off-target liabilities. Structure-activity relationship studies focused on optimizing IDO1 inhibition potency and a pharmacokinetic profile amenable to oral dosing while controlling CYP450 and hERG inhibitory properties.

Dehydrozingerone Inspired Styryl Hydrazine Thiazole Hybrids as Promising Class of Antimycobacterial Agents

Series of styryl hydrazine thiazole hybrids inspired from dehydrozingerone (DZG) scaffold were designed and synthesized by molecular hybridization approach. In vitro antimycobacterial activity of synthesized compounds was evaluated against Mycobacterium tuberculosis H37Rv strain. Among the series, compound 6o exhibited significant activity (MIC = 1.5 μM; IC50 = 0.48 μM) along with bactericidal (MBC = 12 μM) and intracellular antimycobacterial activities (IC50 = 0.098 μM). Furthermore, 6o displayed prominent antimycobacterial activity under hypoxic (MIC = 46 μM) and normal oxygen (MIC = 0.28 μM) conditions along with antimycobacterial efficiency against isoniazid (MIC = 3.2 μM for INH-R1; 1.5 μM for INH-R2) and rifampicin (MIC = 2.2 μM for RIF-R1; 6.3 μM for RIF-R2) resistant strains of Mtb. Presence of electron donating groups on the phenyl ring of thiazole moiety had positive correlation for biological activity, suggesting the importance of molecular hybridization approach for the development of newer DZG clubbed hydrazine thiazole hybrids as potential antimycobacterial agents.

Tuning of excited-state intramolecular proton transfer (ESIPT) fluorescence of imidazo[1,2-a]pyridine in rigid matrices by substitution effect

2-(2′-Hydroxyphenyl)imidazo[1,2-a]pyridine (HPIP, 1) and its derivatives are synthesized, and their fluorescence properties are studied. Although all the compounds show faint dual emission (Φ ≈ 0.01), which is assigned to the normal and excited-state intr

Imidazole derivatives or their salts

Imidazole derivatives of the formula (1) or salts thereof, pharmaceuticals containing the derivatives or the salts, and intermediates for the synthesis of the derivatives or the salts (wherein R1 is lower alkyl; R2 is alkyl or aralkyl; and X1 is halogeno). These compounds exhibit G-CSF-like activities and can be substituted for G-CSF preparations. 1