3328-77-6

Basic information

• Product Name: 2' 4'-DIHYDROXY-5'-NITROACETOPHENONE
• Synonyms: Acetophenone,2',4'-dihydroxy-5'-nitro- (6CI,7CI,8CI);2,4-Dihydroxy-5-nitroacetophenone;5-Nitroresacetophenone;NSC 3928
• CAS NO: 3328-77-6
• Molecular Formula: C₈H₇NO₅
• Molecular Weight: 197.14
• Product Categories: C7 to C8;Carbonyl Compounds;Ketones
• Mol File: 3328-77-6.mol
• Article Data: 5

Chemical Properties

• Melting Point: 142-146 °C(lit.)
• Boiling Point: 347.9 °C at 760 mmHg
• Flash Point: 155.8 °C
• Appearance: /
• Density: 1.52 g/cm³
• Vapor Pressure: 2.59E-05mmHg at 25°C
• Refractive Index: 1.637
• CAS DataBase Reference: 2' 4'-DIHYDROXY-5'-NITROACETOPHENONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2' 4'-DIHYDROXY-5'-NITROACETOPHENONE(3328-77-6)
• EPA Substance Registry System: 2' 4'-DIHYDROXY-5'-NITROACETOPHENONE(3328-77-6)

Safety Data

• Hazard Codes: T
• Statements: 25-36-43
• Safety Statements: 26-36/37
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 3328-77-6(Hazardous Substances Data)

Usage

Preparation

Also obtained by nitration of resacetophenone with zirconyl nitrate in acetone at 50° for 5 h (98%).

InChI:InChI=1/C8H7NO5/c1-4(10)5-2-6(9(13)14)8(12)3-7(5)11/h2-3,11-12H,1H3

Upstream product

• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 108-46-3 recorcinol 
• 29682-12-0 1-[4-(benzyloxy)-2-hydroxyphenyl]ethanone 
• 3163-07-3 4-nitroresorcinol 
• 108-24-7 acetic anhydride 
• 56923-41-2 bis-(5-acetyl-2,4-dihydroxy-phenyl)-sulfide 
• 101097-87-4 1-(4-benzyloxy-2-hydroxy-5-nitro-phenyl)-ethanone 

Downstream Products

• 161959-27-9 5-nitro-benzene-1,2,4-triol 
• 145489-91-4 4-acetyl-3-hydroxy-6-nitro-2-phenyliodonio-phenolate 
• 5528-13-2 1-(5-amino-2,4-dihydroxyphenyl)ethanone 

Relevant articles and documents

2-Acetyl-4-aminoresorcinol derivatives: synthesis, antioxidant activity and molecular docking studies

In this study, we synthesized new phenolic compounds that have the potential to serve as antioxidants and slow the effects of free radicals and oxidizing agents, which is beneficial for human health. Three resorcinol derivatives (new amide compounds) were generated by acetylation, nitration, and reduction. The structures of the products were determined by spectroscopic methods. The antioxidant activities of the new compounds were evaluated in vitro by redox reactions with the free radicals of the diammonium salt of 2,2-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS+●) and 1,1-diphenyl-2-picrylhydrazyl (DPPH●). The tested compounds showed antioxidant activities similar to that of resveratrol, a natural product known to affect a wide range of intracellular mediators. These derivatives were also submitted to docking simulations to evaluate their possible interactions with the enzyme myeloperoxidase. This analysis showed potential interactions with pockets “A” and “B” in the enzyme, and the best interaction was detected between succinic-amide (4) and pocket A.

Highly efficient nitration of phenolic compounds by zirconyl nitrate

Zirconyl nitrate was found to be an excellent reagent in the nitration of phenol and substituted phenols to give nitrated phenols. This procedure works efficiently on most of the examples at room temperature yielding nitro derivatives in fair to good yields with high regioselectivity.

Reaction of Cerium(IV) Ammonium Nitrate with Aralkyl and Aromatic Ketones

Fluoren-9-one on treatment with cerium(IV) ammonium nitrate (CAN) yields five compounds which have been identified as 3-nitro-; 2-nitro; 1,8-dinitro; 2,7-dinitro; and 2,7-dinitrofluoren-9-ones.Acetophenone on treatment with CAN, yields only benzoic acid while 2,4-dihydroxyacetophenone on similar treatment yields three compounds which have been identified as 2,4-dihydroxy-5-nitro; 2,4-dihydroxy-3-nitro; and 2,4-dihydroxy-3,5-dinitro-acetophenones.