5464-98-2

Basic information

• Product Name: 4-HYDROXY-3-NITROBENZOPHENONE
• Synonyms: 4-HYDROXY-3-NITROBENZOPHENONE;3-NITRO-4-HYDROXYBENZOPHENONE;(4-hydroxy-3-nitro-phenyl)-phenyl-methanone;(4-hydroxy-3-nitrophenyl)-phenylmethanone
• CAS NO: 5464-98-2
• Molecular Formula: C₁₃H₉NO₄
• Molecular Weight: 243.21
• Product Categories: Aromatic Benzophenones & Derivatives (substituted)
• Mol File: 5464-98-2.mol
• Article Data: 8

Chemical Properties

• Melting Point: 92-93°C
• Boiling Point: 386.08°C (rough estimate)
• Flash Point: 172.4°C
• Appearance: /
• Density: 1.2929 (rough estimate)
• Vapor Pressure: 4.6E-07mmHg at 25°C
• Refractive Index: 1.5880 (estimate)
• PKA: 5.16±0.14(Predicted)
• CAS DataBase Reference: 4-HYDROXY-3-NITROBENZOPHENONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-HYDROXY-3-NITROBENZOPHENONE(5464-98-2)
• EPA Substance Registry System: 4-HYDROXY-3-NITROBENZOPHENONE(5464-98-2)

Safety Data

• Hazardous Substances Data: 5464-98-2(Hazardous Substances Data)

Usage

Preparation

Preparation by treatment of 4-methylamino-3- nitrobenzo-phenone with boiling 10% aqueous sodium hydroxide for 48 h (52%).

InChI:InChI=1/C13H9NO4/c15-12-7-6-10(8-11(12)14(17)18)13(16)9-4-2-1-3-5-9/h1-8,15H

Upstream product

• 66353-71-7 4-benzoyl-N-methyl-2-nitroaniline 
• 56107-03-0 4-bromo-3-nitrobenzophenone 
• 82571-94-6 4-methoxy-3-nitro-benzophenone 
• 1137-42-4 4-Hydroxybenzophenone 
• 2243-80-3 3-nitrobenzophenone 
• 6284-79-3 3,4-dichlorobenzophenone 
• 37021-63-9 2-nitro-4-benzylphenol 

Downstream Products

• 92497-77-3 (2-methyl-benzooxazol-5-yl)-phenyl-methanone 
• 42404-41-1 (3-amino-4-hydroxy-phenyl)-phenyl-methanone 
• 82593-17-7 (2-phenyl-5-benzoxazolyl)phenylmethanone 
• 82593-18-8 3-benzoylamino-4-hydroxybenzophenone 

Relevant articles and documents

Synthesis, protease inhibition, and antileishmanial activity of new benzoxazoles derived from acetophenone or benzophenone and synthetic precursors

Abstract: This work reports the synthesis, protease inhibition, and antileishmanial activity of ten benzoxazole derivatives, which were obtained in a three-step synthetic route from 4-hydroxy-acetophenone and 4-hydroxy-benzophenone. These benzoxazoles, the synthetic intermediates, and the starting ketones were evaluated for their inhibitory effect on the activity of cysteine (papain, rCPB2.8, and rCPB3.0) and serine (trypsin) proteases. All compounds showed significant values of IC50 against these enzymes (in the range of 0.0086–0.7612 μM for papain and 0.0075–0.5032 μM for trypsin), being more active than the standard inhibitors (1.7821 and 7.2318 μM, for E64 and TLCK, respectively). Following, all compounds were evaluated in vitro for their leishmanicidal activity against promastigote form of Leishmania amazonensis. The most active compounds were further evaluated against amastigote form and for its toxicity against murine macrophages. The benzoxazole 4d, a benzophenone derivative, and the intermediate 4-hydroxy-3-nitroacetophenone 2b showed significant antileishmanial activity (IC50 = 90.3 μM and IC50 = 130.9 μM, respectively) with selectivity indexes (5.22 and 18.09, respectively) compared to or better than those of two established leishmanicidal drugs, pentamidine (0.58) and amphotericin B (5.31). Graphical Abstract: [InlineMediaObject not available: see fulltext.].

An eco-friendly Co(OAc)2-catalyzed aerobic oxidation of 4-benzylphenols into 4-hydroxybenzophenones

An undecorated Co(OAc)2-catalyzed aerobic oxidation system has been reported that enables direct transformation of 4-benzylphenols into the corresponding 4-hydroxybenzophenones. The procedure is especially suitable for electron-withdrawing group-containing substrates, which are commonly inefficient to conduct this category of oxidation. Based on well-defined p-benzoquinone methides and the confirmed ethereal intermediate, a plausible mechanism was depicted.

PEG-N2O4: An efficient nitrating agent for the selective mono- and dinitration of phenols under mild conditions

N2O4 was easily impregnated on polyethyleneglycol to give a stable reagent. The polyethyleneglycol-N2O4 (PEG-N2O4) system was used as an effective nitrating agent for the nitration of phenols. Mono- and dinitrophenols can be obtained via direct nitration of phenols in the presence of PEG-N2O4 at room temperature in moderate to high yields. Copyright Taylor & Francis Group, LLC.