30186-18-6

Basic information

• Product Name: 4-BROMO-2-HYDROXYACETOPHENONE
• Synonyms: ETHANONE, 1-(4-BROMO-2-HYDROXYPHENYL)-;4-BROMO-2-HYDROXYACETOPHENONE;1-(4-BROMO-2-HYDROXY-PHENYL)-ETHANONE;1-(4-Bromo-2-hydroxyphenyl)ethan-1-one;4-Bromo-2-hydroxyacetophenone ,97%;1-(4-Bromo-2-hydroxyphenyl)ethan-1-one, 2-Acetyl-5-bromophenol
• CAS NO: 30186-18-6
• Molecular Formula: C₈H₇BrO₂
• Molecular Weight: 215.04
• EINECS: 1533716-785-6
• Product Categories: Aromatic Acetophenones & Derivatives (substituted)
• Mol File: 30186-18-6.mol
• Article Data: 42

Chemical Properties

• Melting Point: 40.0 to 44.0 °C
• Boiling Point: 83°C/7mmHg(lit.)
• Flash Point: 127.838 °C
• Appearance: /Solid
• Density: 1.586 g/cm³
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.592
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 9.20±0.10(Predicted)
• Water Solubility: Slightly soluble in water.
• CAS DataBase Reference: 4-BROMO-2-HYDROXYACETOPHENONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-BROMO-2-HYDROXYACETOPHENONE(30186-18-6)
• EPA Substance Registry System: 4-BROMO-2-HYDROXYACETOPHENONE(30186-18-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• RIDADR: 1759
• Hazardous Substances Data: 30186-18-6(Hazardous Substances Data)

Usage

Chemical Properties

White to yellow solid

Uses

4'-Bromo-2'-hydroxyacetophenone is used as a pharmaceutical intermediate.

Preparation

Preparation by diazotization of 5-amino-3-bromo-2- hydroxyacetophenone, followed by hydrolysis of the obtained diazonium salt (51%).

InChI:InChI=1/C8H7BrO2/c1-5(10)7-3-2-6(9)4-8(7)11/h2-4,11H,1H3

Upstream product

• 591-20-8 3-Bromophenol 
• 75-36-5 acetyl chloride 
• 135715-84-3 4-(5-fluoro-3-mercaptophenyl)-4-methoxytetrahydropyran 
• 161386-22-7 4'-[5-fluoro-3-(4-methoxytetrahydropyran-4-yl)phenylthio]-2'-methoxyacetophenone 
• 7664-93-9 sulfuric acid 
• 89368-12-7 1-[4-bromo-2-(methyloxy)phenyl]ethanone 
• 625446-22-2 4-bromo-2-fluoroacetophenone 
• 108-24-7 acetic anhydride 
• 2142-63-4 1-(3-Bromophenyl)ethanone 
• 75-16-1 methylmagnesium bromide 
• 288067-35-6 4-bromo-2-hydroxy-benzonitrile 
• 2398-37-0 3-methoxyphenyl bromide 
• 35065-86-2 3-bromophenyl acetate 

Downstream Products

• 132020-64-5 (E)-3-(4-Benzyloxy-phenyl)-1-(4-bromo-2-hydroxy-phenyl)-propenone 
• 130200-01-0 7-Bromo-2,2-dimethyl-2,3-dihydro-4H-chromen-4-one 
• 89368-12-7 1-[4-bromo-2-(methyloxy)phenyl]ethanone 
• 91721-00-5 ethyl (2-acetyl-5-bromophenoxy)acetate 
• 801220-43-9 7-bromo-4'-(diethylamino)-3-hydroxyflavone 
• 843646-45-7 (6-bromo-3-methyl-benzofuran-2-yl)-(2,4-dichloro-phenyl)-methanone 
• 843646-63-9 2,4-dichloro-benzoic acid 2-acetyl-5-bromo-phenyl ester 
• 403793-84-0 7-Bromospiro[2H-1-benzopyran-2,1'cyclopentan]-4(3H)-one 
• 403793-82-8 7-bromospiro[chroman-2,1'-cyclobutan]-4-one 
• 161385-97-3 1-[2-(benzyloxy)-4-bromophenyl]ethanone 
• 102297-62-1 3-hydroxy-4-(1-oxo-ethane)benzoic acid 
• 690632-38-3 tert-butyl 6-bromo-4-oxo-3,4-dihydro-1'H-spiro[chromene-2,4'-piperidine]-1'-carboxylate 
• 936648-38-3 tert-butyl 7-bromo-4-oxospiro[chroman-2,4′-piperidine]-1′-carboxylate 
• 925922-62-9 1-[4-bromo-2-(methoxymethoxy)phenyl]ethan1-one 

Relevant articles and documents

Design, synthesis and biological evaluation of biphenyl urea derivatives as novel VEGFR-2 inhibitors

VEGFR-2 plays a critical role in vasculogenesis and VEGFR-2 inhibitors have been widely used in the treatment of cancer. In our continued efforts to search for potent and novel VEGFR-2 inhibitors as antitumor agents, we have identified a potent lead compound (HMQ-16) bearing a biphenyl scaffold. Rearrangement and replacement of arylcarbamoyl in HMQ-16 with a urea moiety generated a series of novel VEGFR-2 inhibitors. In order to enhance the affinity with VEGFR-2, the 4′-acetyl group was converted to an oxime group. Fourteen biphenyl urea derivatives were designed and synthesized as potent VEGFR-2 inhibitors. Six of them (T2, T5, T7, T9, T11, T14) exhibited potent VEGFR-2 inhibitory activity comparable to that of sorafenib. Compound T7 was the most potent with an IC 50 value of 1.08 nM. The enzymatic and cellular assays suggested that T7 has potential as a valuable lead compound for further optimization.

Radical-anion coupling through reagent design: hydroxylation of aryl halides

The design and development of an oxime-based hydroxylation reagent, which can chemoselectively convert aryl halides (X = F, Cl, Br, I) into phenols under operationally simple, transition-metal-free conditions is described. Key to the success of this approach was the identification of a reducing oxime anion which can interact and couple with open-shell aryl radicals. Experimental and computational studies support the proposed radical-nucleophilic substitution chain mechanism.

INHIBITORS OF HEPATITIS C VIRUS REPLICATION

The present invention relates to compounds of formula (I) that are useful as hepatitis C virus (HCV) NS5A inhibitors, the synthesis of such compounds, and the use of such compounds for inhibiting HCV NS5A activity, for treating or preventing HCV infections and for inhibiting HCV viral replication and/or viral production in a cell-based system.