2491-39-6

Basic information

• Product Name: 2-HYDROXY-1-(4-HYDROXY-PHENYL)-ETHANONE
• Synonyms: DIHYDROXY BROMOACETOPHENONE;2,4-DIHYDROXYPHENACYL BROMIDE;2-HYDROXY-1-(4-HYDROXY-PHENYL)-ETHANONE;2-BROMO-2',4'-DIHYDROXYACETOPHENONE;1-(2,4-dihydroxyphenyl)-2-bromoethanone;2-Bromo-2',4'-dihydroxyacetophenone, 2-Bromo-1-(2,4-dihydroxyphenyl)ethan-1-one, 4-(Bromoacetyl)resorcinol;2-broMo-1-(2,4-dihydroxyphenyl)ethan-1-one;2-Bromo-2',4'-dihydroxyacetophenone 95%
• CAS NO: 2491-39-6
• Molecular Formula: C₈H₇BrO₃
• Molecular Weight: 231.04
• Product Categories: pharmacetical;API intermediates;C7 to C8;Carbonyl Compounds;Ketones
• Mol File: 2491-39-6.mol
• Article Data: 9

Chemical Properties

• Melting Point: 128-132 °C(lit.)
• Boiling Point: 367.212 °C at 760 mmHg
• Flash Point: 175.9 °C
• Appearance: /
• Density: 1.764 g/cm³
• Vapor Pressure: 6.56E-06mmHg at 25°C
• Refractive Index: 1.649
• PKA: 7.28±0.35(Predicted)
• CAS DataBase Reference: 2-HYDROXY-1-(4-HYDROXY-PHENYL)-ETHANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-HYDROXY-1-(4-HYDROXY-PHENYL)-ETHANONE(2491-39-6)
• EPA Substance Registry System: 2-HYDROXY-1-(4-HYDROXY-PHENYL)-ETHANONE(2491-39-6)

Safety Data

• Hazard Codes: C
• Statements: 22-34-43
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 2491-39-6(Hazardous Substances Data)

Usage

General Description

2-HYDROXY-1-(4-HYDROXY-PHENYL)-ETHANONE, also known as p-hydroxyphenylacetylacetone, is a chemical compound with the molecular formula C10H10O3. It is a yellow to beige crystalline powder with a melting point of around 170-172°C. 2-HYDROXY-1-(4-HYDROXY-PHENYL)-ETHANONE is commonly used as a chelating agent in coordination chemistry and as a ligand in the synthesis of metal complexes. It has also been studied for its potential pharmacological properties, including its antioxidant and anti-inflammatory effects, making it a potential candidate for the development of new drugs. Additionally, 2-HYDROXY-1-(4-HYDROXY-PHENYL)-ETHANONE has been investigated for its potential applications in analytical chemistry and as a catalyst in organic synthesis.

InChI:InChI=1/C8H7BrO3/c9-4-8(12)6-2-1-5(10)3-7(6)11/h1-3,10-11H,4H2

Upstream product

• 108-46-3 recorcinol 
• 590-17-0 cyanomethyl bromide 
• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 598-21-0 2-Bromoacetyl bromide 

Downstream Products

• 797813-79-7 4-(2-(4-hydroxyphenylamino)thiazol-4-yl)benzene-1,3-diol 
• 1173282-19-3 4-(2-(2-hydroxyphenylamino)thiazol-4-yl)benzene-1,3-diol 
• 1173282-17-1 4-(2-(3-hydroxyphenylamino)thiazol-4-yl)benzene-1,3-diol 
• 924173-79-5 4-(2-(phenylamino)thiazol-4-yl)benzene-1,3-diol 
• 1067911-22-1 4-(2-methylthiazol-4-yl)benzene-1,3-diol 
• 1220915-50-3 3-(2,4-dihydroxyphenyl)-1-ethyl-6-methylpyridazino[3,4-d]pyrimidine-5,7(1H,6H)-dione 
• 6272-26-0 6-hydroxybenzofuran-3-one 
• 1335016-14-2 4-(2-cyclopropylimidazo[2,1-b][1,3,4]thiadiazol-6-yl)benzene-1,3-diol 
• 202131-29-1 V⁽¹⁹⁴⁾U₀₂₉₃ 
• 1394893-17-4 4-(2-(biphenyl-4-yl)imidazo[2,1-b][1,3,4]thiadiazol-6-yl)benzene-1,3-diol 
• 1414626-98-4 4-(2-(4-methoxyphenyl)imidazo[2,1-b][1,3,4]thiadiazol-6-yl)benzene-1,3-diol 
• 1414627-32-9 4-(2-(2-chloro-5-nitrophenyl)imidazo[2,1-b][1,3,4]thiadiazol-6-yl)benzene-1,3-diol 
• 1556096-88-8 4, 4′-(4-nitrobenzylidene)-bis-[3-(2′,4′-dihyroxybenzoyl)-1H-2-benzopyran-1-one] 
• 1556096-89-9 4, 4'-(4-hydroxybenzylidene)-bis-[3-(2',4'-dihydroxybenzoyl)-1H-2-benzopyran-1-one] 

Relevant articles and documents

Nucleus-independent chemical shift (NICS) as a criterion for the design of new antifungal benzofuranones

The assertion made by Wu et al. that aromaticity may have considerable implications for molecular design motivated us to use nucleus-independent chemical shifts (NICS) as an aromaticity criterion to evaluate the antifungal activity of two series of indol-4-ones. A linear regression analysis of NICS and antifungal activity showed that both tested variables were significantly related (p –1 for Candida glabrata, Candida krusei and Candida guilliermondii with compounds 15-32, 15-15 and 15-1. The MIC for filamentous fungi was 1.95 μg·mL–1 for Aspergillus niger for compounds 15-1, 15-33 and 15-34. The results obtained support the use of NICS in the molecular design of compounds with antifungal activity.

Synthesis and in vitro characterization of some benzothiazole- and benzofuranone-derivatives for quantification of fibrillar aggregates and inhibition of amyloid-mediated peroxidase activity

Neurodegenerative diseases are characterized by amyloid deposition. Thioflavin T (ThT) is one of the molecules considered for detection of amyloid deposits; however, its lipophilicity is too low to cross the blood-brain barrier. Therefore, there is a strong motivation to develop suitable compounds for in vitro fibril quantification as well as for in vivo amyloid imaging. Moreover, oxidative stress (particularly, uncontrolled peroxidase activity) has frequently been reported to play a critical role in the onset/progression of some neurodegenerative disorders. In this study, we describe the synthesis of some benzothiazole and benzofuranone compounds and examine their peroxidase inhibitory properties. Furthermore, to establish the potential binding of synthesized compounds to amyloid aggregates, their in vitro binding to some non-disease related amyloidogenic proteins were characterized. Analyses of the in vitro binding studies indicated that compounds 2 and 4 bind to the amyloid structures successfully while compounds 1 and 3 showed a low affinity in binding to fibrils. Furthermore, compounds 3 and 4 were observed to inhibit amyloid-mediated peroxidase activity in a reversible un-competitive manner.

Functionalized aurones as inducers of NAD(P)H:quinone oxidoreductase 1 that activate AhR/XRE and Nrf2/ARE signaling pathways: Synthesis, evaluation and SAR

The chemopreventive potential of functionalized aurones and related compounds as inducers of NAD(P)H:quinone oxidoreductase 1 (NQO1, EC 1.6.99.2) are described. Several 4,6-dimethoxy and 5-hydroxyaurones induced NQO1 activity of Hepa1c1c7 cells by 2-fold at submicromolar concentrations, making these the most potent inducers to be identified from this class. Mechanistically, induction of NQO1 was mediated by the activation of AhR/XRE and Nrf2/ARE pathways, indicating that aurones may be mixed activators of NQO1 induction or agents capable of exploiting the proposed cross-talk between the AhR and Nrf2 gene batteries. QSAR analysis by partial least squares projection to latent structures (PLS) identified size parameters, in particular those associated with non-polar surface areas, as an important determinant of induction activity. These were largely determined by the substitution on rings A and B. A stereoelectronic role for the exocyclic double bond as reflected in the E LUMO term was also identified. The electrophilicity of the double bond or its effect on the conformation of the target compound are possible key features for induction activity.