51288-37-0

Basic information

• Product Name: N-(4-hydroxy-3-nitrophenyl)acetamide
• Synonyms: N-(4-hydroxy-3-nitrophenyl)acetamide;4-(Acetylamino)-2-nitrophenol;Einecs 257-113-5;Nsc 212489
• CAS NO: 51288-37-0
• Molecular Formula: C₈H₈N₂O₄
• Molecular Weight: 196.16012
• EINECS: 257-113-5
• Mol File: 51288-37-0.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 394.9°Cat760mmHg
• Flash Point: 192.6°C
• Appearance: /
• Density: 1.477g/cm³
• Vapor Pressure: 8.39E-07mmHg at 25°C
• Refractive Index: 1.658
• CAS DataBase Reference: N-(4-hydroxy-3-nitrophenyl)acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(4-hydroxy-3-nitrophenyl)acetamide(51288-37-0)
• EPA Substance Registry System: N-(4-hydroxy-3-nitrophenyl)acetamide(51288-37-0)

Safety Data

• Hazardous Substances Data: 51288-37-0(Hazardous Substances Data)

Usage

General Description

N-(4-hydroxy-3-nitrophenyl)acetamide is a chemical compound with the molecular formula C8H8N2O4. It is a derivative of acetamide and contains a hydroxy and nitro group attached to a phenyl ring. N-(4-hydroxy-3-nitrophenyl)acetamide is primarily used in the synthesis of other organic compounds and pharmaceuticals. It has potential applications as an intermediate in the production of dyes and pigments, as well as in the development of new drugs. N-(4-hydroxy-3-nitrophenyl)acetamide is not widely known for its specific uses, but its structure and properties make it a promising candidate for further research and development in various chemical and pharmaceutical applications.

InChI:InChI=1/C8H8N2O4/c1-5(11)9-6-2-3-8(12)7(4-6)10(13)14/h2-4,12H,1H3,(H,9,11)

Upstream product

• 103-90-2 4-acetaminophenol 
• 855931-50-9 1-acetoxy-4-acetylamino-2-nitro-benzene 
• 108-24-7 acetic anhydride 
• 123-30-8 4-amino-phenol 
• 7664-93-9 sulfuric acid 
• 7697-37-2 nitric acid 
• 119-34-6 4-amino-2-nitrophenol 

Downstream Products

• 219555-88-1 N-{4-[2-(5-Methyl-2-nitro-phenoxy)-ethoxy]-3-nitro-phenyl}-acetamide 
• 219555-91-6 {3-Amino-4-[2-(2-amino-5-methyl-phenoxy)-ethoxy]-phenyl}-carbamic acid tert-butyl ester 
• 219555-89-2 4-[2-(5-Methyl-2-nitro-phenoxy)-ethoxy]-3-nitro-phenylamine 
• 219555-90-5 {4-[2-(5-Methyl-2-nitro-phenoxy)-ethoxy]-3-nitro-phenyl}-carbamic acid tert-butyl ester 
• 219555-93-8 [(5-Amino-2-{2-[2-(bis-methoxycarbonylmethyl-amino)-5-methyl-phenoxy]-ethoxy}-phenyl)-methoxycarbonylmethyl-amino]-acetic acid methyl ester 
• 219555-92-7 [(2-{2-[2-(Bis-methoxycarbonylmethyl-amino)-5-methyl-phenoxy]-ethoxy}-5-tert-butoxycarbonylamino-phenyl)-methoxycarbonylmethyl-amino]-acetic acid methyl ester 
• 855880-76-1 N-Acetyl-sulfanilsaeure-(5-acetamino-2-hydroxy-anilid) 
• 59820-33-6 (4-acetylamino 2-nitro)phenoxyethanol 
• 67499-19-8 bis-(2-nitro-4-amino-phenoxy)-methane 
• 1313574-50-3 7-nitro-8-oxo-1,2,3,4-tetraphenylspiro[4.5]deca-1,3,6,9-tetraene 
• 56428-73-0 3-(4-hydroxy-3-nitrophenyl)-2-propenoic acid methyl ester 
• 3001-06-7 (E)-2-nitro-4-(4-nitrostyryl)phenol 
• 1252036-52-4 4-hydroxy-3-nitrobenzenediazonium tetrafluoroborate 
• 1223466-35-0 4-benzyloxy-3-nitroacetanilide 

Relevant articles and documents

Conjugation of nitrated acetaminophen to Der p1 amplifies peripheral blood monocyte response to Der p1

Background: An association of acetaminophen use and asthma was observed in the International Study of Asthma and Allergies in Childhood study. However there are no clear mechanisms to explain an association between acetaminophen use and immunologic pathology. In acidic conditions like those in the stomach and inflamed airway, tyrosine residues are nitrated by nitrous and peroxynitrous acids. The resulting nitrotyrosine is structurally similar to 2,4-dinitrophenol and 2,4-dinitrochlorobenzene, known haptens that enhance immune responses by covalently binding proteins. Nitrated acetaminophen shares similar molecular structure. Objective: We hypothesized the acetaminophen phenol ring undergoes nitration under acidic conditions, producing 3-nitro-acetaminophen which augments allergic responses by acting as a hapten for environmental allergens. Methods: 3-nitro-acetaminophen was formed from acetaminophen in the presence of acidified nitrite, purified by high performance liquid chromatography, and assayed by gas-chromatography mass spectrometry. Purified 3-nitro-acetaminophen was reacted with Dermatophagoides pteronyssinus (Der p1) and analyzed by mass spectrometry to identify the modification site. Human peripheral blood mononuclear cells proliferation response was measured in response to 3-nitro-acetaminophen and to 3-nitro-acetaminophen-modified Der p1. Results: Acetaminophen was modified by nitrous acid forming 3-nitro-acetaminophen over a range of different acidic conditions consistent with airway inflammation and stomach acidity.

Nitrating reactive nitric oxygen species transform acetaminophen 3-nitroacetaminophen

Nitrating reactive nitric oxygen species (RNOS) elicit many of the deleterious effects of the inflammatory response. Their high reactivity and short half-life make RNOS analysis difficult. Reaction of acetaminophen (APAP) with RNOS generated by various conditions was evaluated by HPLC. When [14C]APAP was incubated at pH 7.4, the same new product (3NAP) was produced by at least three separate pathways represented by the following conditions: myeloperoxidase oxidation of NO2-, NO2Cl, and ONOO- or Sin-1. Diethylamine NONO and spermine NONO did not convert APAP to 3NAP. 3NAP was stable at pH 5, 7.4, or 9, and at pH 7.4 with ONOO-, spermine NONO, Sin-1, or H2O2. HOCl transformed 3NAP, which was prevented by APAP, ascorbic acid, taurine, or NO2-. ONOO--derived 3NAP was identified by 1H NMR as 3-nitroacetaminophen or 3-nitro-N-acetyl-p-aminophenol, and the product mass was verified by EI/ESI mass spectrometry. Human polymorphonuclear neutrophils incubated with [14C]APAP and stimulated with β-phorbol 12-myristate 13-acetate produced 3NAP in the presence of NO2-. Neutrophil 3NAP formation was verified by mass spectrometry and was consistent with myeloperoxidase oxidation of NO2-. Spermine NONO supported 3NAP formation by stimulated cells in the absence of NO2-. Results demonstrate that 3NAP is a product of nitrating RNOS generated by at least three separate pathways and may be a biomarker for nitrating mediators of inflammation.

A practical approach for regioselective mono-nitration of phenols under mild conditions

Cu(NO3)2.3H2O was demonstrated to be an efficient, regioselective and inexpensive nitrating reagent for the synthesis of mono-nitro substituted phenolic compounds. 12 examples of different phenols were examined. Good yields (67-90%) have been achieved. ARKAT-USA, Inc.