137987-89-4

Basic information

• Product Name: 1-(2,4-dihydroxyphenyl)-2-(4-nitrophenoxy)ethanone
• Synonyms: 1-(2,4-dihydroxyphenyl)-2-(4-nitrophenoxy)ethanone;Ethanone, 1-(2,4-dihydroxyphenyl)-2-(4-nitrophenoxy)-
• CAS NO: 137987-89-4
• Molecular Formula: C₁₄H₁₁NO₆
• Molecular Weight: 289.2402
• Mol File: 137987-89-4.mol

Chemical Properties

• Melting Point: 281°C
• Boiling Point: 556.6°C at 760 mmHg
• Flash Point: 290.4°C
• Density: 1.46g/cm³
• Vapor Pressure: 5.39E-13mmHg at 25°C
• Refractive Index: 1.656
• PKA: 7.17±0.35(Predicted)
• CAS DataBase Reference: 1-(2,4-dihydroxyphenyl)-2-(4-nitrophenoxy)ethanone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2,4-dihydroxyphenyl)-2-(4-nitrophenoxy)ethanone(137987-89-4)
• EPA Substance Registry System: 1-(2,4-dihydroxyphenyl)-2-(4-nitrophenoxy)ethanone(137987-89-4)

Safety Data

• Hazardous Substances Data: 137987-89-4(Hazardous Substances Data)

Usage

Preparation

Obtained by reaction of p-nitrophenoxyacetonitrile with resorcinol (Hoesch reaction) (86%).

Upstream product

• 33901-46-1 2-(4-nitrophenoxy)acetonitrile 
• 108-46-3 recorcinol 
• 100-02-7 4-nitro-phenol 

Downstream Products

• 137988-02-4 7-Hydroxy-3-(4-nitro-phenoxy)-chromen-4-one 
• 137988-18-2 Acetic acid 3-(4-nitro-phenoxy)-4-oxo-4H-chromen-7-yl ester 

Relevant articles and documents

ANTI-VIRULENCE COMPOSITIONS AND METHODS

A method of reducing the virulence of a bacterium that expresses accessory gene regulator A (AgrA) or an ortholog of AgrA includes administering to the bacterium an amount of a pharmaceutical composition effective to inhibit the synthesis of one or more virulence factors by the bacterium, the pharmaceutical composition including an AgrA antagonist.

Combinatorial synthesis and in vitro evaluation of a biaryl hydroxyketone library as antivirulence agents against mrsa

Antibiotic resistance coupled with decreased development of new antibiotics necessitates the search for novel antibacterial agents. Antivirulence agents offer an alternative to conventional antibiotics. In this work, we report on a family of small-molecule antivirulence agents against methicillin-resistant Staphylococcus aureus (MRSA), the most widespread bacterial pathogen. Structure-activity relationship studies led to the development of a concise synthesis of a 148-member biarylhydroxyketone library. An acylation bond-forming process afforded resorcinols (1) and aryloxy acetonitriles (2) as synthons. A Lewis-acid-activated Friedel-Crafts' acylation step involving a nitrile functionality of 2 by ZnCl2, followed by nucleophilic attack by 1 was executed to obtain biaryl hydroxyketones in excellent yields. A large number of products crystallized. This strategy affords a range of biarylhydroxyketones in a single step. This is the first collective synthetic study documenting access to this class of compounds through a single synthetic operation. In vitro efficacy of compounds in this library was evaluated by a rabbit erythrocyte hemolysis assay. The most efficacious compound, 4f-12, inhibits hemolysis by 98.1 ± 0.1% compared to control in the absence of the compound.