8055-08-1

Basic information

• Product Name: N-(4-hydroxyphenyl)acetamide
• Synonyms: Pantoprazole Impurity 43;TIANFU-CHEM CAS:8055-08-1 N-(4-hydroxyphenyl)acetamide
• CAS NO: 8055-08-1
• Molecular Formula: C8H9NO2
• Molecular Weight: 0
• Mol File: 8055-08-1.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-(4-hydroxyphenyl)acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(4-hydroxyphenyl)acetamide(8055-08-1)
• EPA Substance Registry System: N-(4-hydroxyphenyl)acetamide(8055-08-1)

Safety Data

• Hazardous Substances Data: 8055-08-1(Hazardous Substances Data)

Usage

Uses

Used in Pain Relief Applications:
N-(4-hydroxyphenyl)acetamide is used as an analgesic for the relief of headaches and other minor aches and pains. It is effective in managing mild to moderate pain and is a common ingredient in various cold and flu remedies.
Used in Fever Reduction Applications:
N-(4-hydroxyphenyl)acetamide is used as an antipyretic to reduce fever. It helps in lowering body temperature in cases of fever and is often included in medications designed to alleviate fever symptoms.
Used in Combination with Opioid Analgesics for Severe Pain Management:
In the pharmaceutical industry, N-(4-hydroxyphenyl)acetamide is used in combination with opioid analgesics for the management of more severe pain, such as post-surgical pain or providing palliative care in advanced cancer patients. This combination enhances the pain-relieving effects and helps in managing severe pain more effectively.
Used in Drug Formulation for Pain and Fever Relief:
N-(4-hydroxyphenyl)acetamide is used as an active ingredient in various drug formulations, including tablets, capsules, and liquid suspensions, for the treatment of pain and fever. It is a popular choice due to its effectiveness and wide availability over the counter.

Upstream product

• 100-02-7 4-nitro-phenol 
• 805233-94-7 1-(4-hydroxy-phenyl)-ethanone-hydrazone 
• 70453-52-0 mercapto-acetic acid-(4-hydroxy-anilide) 
• 108-24-7 acetic anhydride 
• 123-30-8 4-amino-phenol 
• 64-19-7 acetic acid 
• 51-78-5 p-aminophenol hydrochloride 
• 463-51-4 Ketene 
• 75-36-5 acetyl chloride 
• 70-18-8 glutathion 
• 50700-49-7 N-acetyl-p-benzoquinoneimine 
• 7218-04-4 N-Acetylcysteine 
• 5003-48-5 Fenasprate 
• 1795-83-1 N-Phenylacetohydroxamic acid 

Downstream Products

• 105788-36-1 acetic acid-{4-[2-hydroxy-3-(2-hydroxy-ethoxy)-propoxy]-anilide} 
• 29175-51-7 N-[4-(2-morpholin-4-yl-ethoxy)-phenyl]-acetamide 
• 131976-58-4 acetic acid-[4-(2-hydroxy-3-piperidino-propoxy)-anilide] 
• 120037-25-4 acetic acid-{4-[2-(2-bromo-ethoxy)-ethoxy]-anilide} 
• 26557-77-7 N-(4-(prop-2-yn-1-yloxy)phenyl)acetamide 
• 109185-18-4 acetic acid-[4-(2-ethoxy-ethoxy)-anilide] 
• 117877-74-4 bis-[2-(4-acetylamino-phenoxy)-ethyl]-sulfide 
• 113057-76-4 N-[5-(4-acetylamino-phenoxy)-pentyl]-phthalimide 
• 37987-92-1 bis-(4-acetylamino-phenoxy)-methane 
• 107920-34-3 acetic acid-[4-(3-nitro-phenoxy)-anilide] 
• 90557-93-0 1-acetylamino-4-carbamoyloxy-benzene 
• 92150-30-6 acetic acid-[4-hydroxy-3-(2-nitro-phenylazo)-anilide] 
• 13245-56-2 1-acetylamino-4-(4-nitro-benzoyloxy)-benzene 
• 13546-95-7 4-nitro-trans-cinnamic acid-(4-acetylamino-phenyl ester) 

Relevant articles and documents

Pyridazine N-Oxides as Photoactivatable Surrogates for Reactive Oxygen Species

A method for the photoinduced evolution of atomic oxygen from pyridazine N-oxides was developed. This underexplored oxygen allotrope mediates arene C-H oxidation within complex, polyfunctional molecules. A water-soluble pyridazine N-oxide was also developed and shown to promote photoinduced DNA cleavage in aqueous solution. Taken together, these studies highlight the utility of pyridazine N-oxides as photoactivatable O(3P) precursors for applications in organic synthesis and chemical biology.

Direct Synthesis of Paracetamol via Site-Selective Electrochemical Ritter-type C-H Amination of Phenol

The synthesis of paracetamol still relies on multistep protocols involving the utilization of a stoichiometric amount of oxidizing/reducing or other corrosive agents. Herein we report a regioselective electrochemical Ritter-type reaction at the C(sp2)-H of unprotected phenol toward the environmentally benign and direct synthesis of paracetamol. The reaction proceeds under exogenous oxidant- and catalyst-free conditions. The protocol is scalable, can be deployed to a variety of phenols, and offers a sustainable alternative for the synthesis of paracetamol.

Redox-Neutral Selenium-Catalysed Isomerisation of para-Hydroxamic Acids into para-Aminophenols

A selenium-catalysed para-hydroxylation of N-aryl-hydroxamic acids is reported. Mechanistically, the reaction comprises an N?O bond cleavage and consecutive selenium-induced [2,3]-rearrangement to deliver para-hydroxyaniline derivatives. The mechanism is studied through both 18O-crossover experiments as well as quantum chemical calculations. This redox-neutral transformation provides an unconventional synthetic approach to para-aminophenols.

Ethyl 2-Cyano-2-(2-nitrobenzenesulfonyloxyimino) Acetate (ortho-NosylOXY)-Mediated Double Beckmann Rearrangement of Ketoximes under Microwave Irradiation: A Mechanistic Perception

A method for Beckmann rearrangement using ethyl 2-cyano-2-(2-nitrobenzenesulfonyloxyimino) acetate (o-NosylOXY) under microwave irradiation is reported. Ketoximes (19 examples) are converted to the corresponding amides/lactams with 69–97% yields in ～10 minutes without any Lewis acid or co-catalyst. This is an example of halogen-free organocatalytic Beckmann rearrangement. Nuclear magnetic resonance (NMR)- and high-resolution mass spectrometry (HRMS)-based detailed mechanistic investigation suggest that o-NosylOXY acts as an initiator. Such initiators are reported before based on density functional theory (DFT) calculations. However, we report here the HRMS signatures of two transient intermediates, the nitrilium ion and the nitrilium ion's dimeric species. Rigorous NMR-based investigation of the reaction mechanism is performed. Our results indicate that the reported Beckmann rearrangement proceeds via two consecutive rearrangements. (Figure presented.).

Beckmann rearrangement of ketoximes promoted by cyanuric chloride and dimethyl sulfoxide under a mild condition

Synthesis of amides via Beckmann rearrangement of ketoximes promoted by cyanuric chloride (TCT)/DMSO under mild conditions has been reported. Conditions of the Beckmann rearrangement, e.g., solvents, the ratios of TCT/DMSO, and the temperature, were investigated using diphenylmethanone oxime as a substrate. The optimized conditions were adopted to afford fourteen amides with yields ranging from 20% to 99%. A plausible mechanism involving an active dimethyl alkoxysulfonium intermediate was proposed according to the mass spectrometry analysis. To our best knowledge, this is the first case of study on Beckmann rearrangement of ketoximes promoted by TCT/DMSO under a mild condition to afford amides efficiently.

Nickel-catalyzed deallylation of aryl allyl ethers with hydrosilanes

An efficient and mild catalytic deallylation method of aryl allyl ethers is developed, with commercially available Ni(COD)2 as catalyst precursor, simple substituted bipyridine as ligand and air-stable hydrosilanes. The process is compatible with a variety of functional groups and the desired phenol products can be obtained with excellent yields and selectivity. Besides, by detection or isolation of key intermediates, mechanism studies confirm that the deallylation undergoes η3-allylnickel intermediate pathway.

Dehydrative Beckmann rearrangement and the following cascade reactions

The Beckmann rearrangement has been predominantly studied for the synthesis of amide and lactam. By strategically using the in situ generated Appel's salt or Mitsunobu's zwitterionic adduct as the dehydrating agent, a series of Beckmann rearrangement and following cascade reactions have been developed herein. The protocol allows the conversion of various ketoximes into amide, thioamide, tetrazole and imide products in modular procedures. The generality and tolerance of functionalities of this method have been demonstrated.

Iron-catalyzed arene C-H hydroxylation

The sustainable, undirected, and selective catalytic hydroxylation of arenes remains an ongoing research challenge because of the relative inertness of aryl carbon-hydrogen bonds, the higher reactivity of the phenolic products leading to over-oxidized by-products, and the frequently insufficient regioselectivity. We report that iron coordinated by a bioinspired L-cystine-derived ligand can catalyze undirected arene carbon-hydrogen hydroxylation with hydrogen peroxide as the terminal oxidant. The reaction is distinguished by its broad substrate scope, excellent selectivity, and good yields, and it showcases compatibility with oxidation-sensitive functional groups, such as alcohols, polyphenols, aldehydes, and even a boronic acid. This method is well suited for the synthesis of polyphenols through multiple carbon-hydrogen hydroxylations, as well as the late-stage functionalization of natural products and drug molecules.

Method for promoting iron-catalyzed oxidation of aromatic compound carbon - hydrogen bond to synthesize phenol by ligand

The method comprises the following steps: iron is used as - a catalyst metal; a sulfur-containing amino acid or cystine-derived dipeptide is a ligand; and under the common action of hydrogen peroxide as an oxidizing agent, an aromatic compound is synthesized to prepare a phenol. Under the action of an acid as an accelerant and hydrogen peroxide as an oxidizing agent, the aryl carbon - hydrogen bond is directly hydroxylated to form a phenolic compound, and the method for preparing the phenol by the catalytic oxidation reaction has a plurality of advantages. The reaction raw materials, the oxidant and the promoter are wide in source, low in price, environment-friendly and good in stability. The aromatic compound carbon - hydrogen bonds directly participate in the reaction to react in one step to form phenol. The reaction condition is mild, the functional group compatibility and the application range are wide. The reaction selectivity is good; under the optimized reaction conditions, the target product separation yield can reach 85%.

In vitro evaluations for pharmacokinetic drug-drug interactions of a novel serotonin-dopamine activity modulator, brexpiprazole

Brexpiprazole, a serotonin-dopamine activity modulator, is indicated for the treatment of schizophrenia and also adjunctive therapy to antidepressants for the treatment of Major Depressive Disorder. To determine the drug–drug interaction risk for cytochrome P450, and SLC and ABC transporters, brexpiprazole and its metabolite, DM-3411 were assessed in this in?vitro investigation. Brexpiprazole exhibited weak inhibitory effects (IC50 >13 μmol/L) on CYP2C9, CYP2C19, CYP2D6 and CYP3A4 activities, but had moderate inhibitor activity on CYP2B6 (IC50 8.19 μmol/L). The ratio of systemic unbound concentration (3.8 nmol/L) to the Ki value was sufficiently low. DM-3411 had comparable inhibitory potentials with brexpiprazole only for CYP2D6 and CYP3A4. The mRNA expressions of CYP1A2, CYP2B6 and CYP3A4 were not changed by the exposure of brexpiprazole to human hepatocytes. Brexpiprazole and DM-3411 exhibited weak or no inhibitory effects for hepatic and renal transporters (OATPs, OATs, OCTs, MATE1, and BSEP), except for MATE-2K (0.156 μmol/L of DM-3411), even for which the ratio to systemic unbound concentration (5.3 nmol/L) was sufficiently low. Brexpiprazole effected the functions of P-gp and BCRP with IC50 values of 6.31 and 1.16 μmol/L, respectively, however, the pharmacokinetic alteration was not observed in the clinical concomitant study on P-gp and BCRP substrates. These in?vitro data suggest that brexpiprazole is unlikely to cause clinically relevant drug interactions resulting from the effects on CYPs or transporters mediating the absorption, metabolism, and/or disposition of co-administered drugs.