6375-17-3

Usage

General Description

Solid.

Reactivity Profile

Compounds in this group do not behave as organic alcohols, as one might guess from the presence of a hydroxyl (-OH) group in their structure. Instead, they react as weak organic acids. Phenols and cresols are much weaker as acids than common carboxylic acids (phenol has Ka = 1.3 x 10^[-10]). These materials are incompatible with strong reducing substances such as hydrides, nitrides, alkali metals, and sulfides. Flammable gas (H2) is often generated, and the heat of the reaction may ignite the gas. Heat is also generated by the acid-base reaction between phenols and bases. Phenols are sulfonated very readily (for example, by concentrated sulfuric acid at room temperature). The reactions generate heat. Phenols are also nitrated very rapidly, even by dilute nitric acid. Nitrated phenols often explode when heated. Many of them form metal salts that tend toward detonation by rather mild shock. Flammable gases are formed by the reaction of organic amides with strong reducing agents. Amides are very weak bases (weaker than water). Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NOx).

Fire Hazard

Flash point data for 2-Acetamido-4-methylphenol are not available. 2-Acetamido-4-methylphenol is probably combustible.

InChI:InChI=1/C9H11NO2/c1-6-3-4-9(12)8(5-6)10-7(2)11/h3-5,12H,1-2H3,(H,10,11)

Upstream product

• 5676-58-4 2,5-dimethyl-1,3-benzoxazole 
• 75813-74-0 2-acetamido-4-methylphenyl acetate 
• 108-24-7 acetic anhydride 
• 95-84-1 3-amino-4-hydroxytoluene 
• 62-53-3 aniline 
• 952-47-6 2-hydroxy-5-methylazobenzene 
• 7664-93-9 sulfuric acid 
• 26054-05-7 acetic acid-(4-methyl-2-phenylazo-phenyl ester) 
• 60-35-5 acetamide 
• 106-44-5 p-cresol 
• 119-33-5 4-methyl-2-nitrophenol 
• 64-19-7 acetic acid 
• 5720-05-8 4-methylphenylboronic acid 
• 220464-86-8 N-(4-methylphenoxy)phthalimide 

Downstream Products

• 5676-58-4 2,5-dimethyl-1,3-benzoxazole 
• 2639-35-2 2-(4-chloro-styryl)-5-methyl-benzooxazole 
• 73916-09-3 5-methyl-2-(4-nitro-styryl)-benzooxazole 
• 73916-06-0 4-[(E)-2-(5-Methyl-benzooxazol-2-yl)-vinyl]-phenol 
• 73916-07-1 2-[(E)-2-(4-Methoxy-phenyl)-vinyl]-5-methyl-benzooxazole 
• 27123-77-9 4-[2-(5-methyl-benzooxazol-2-yl)-vinyl]-benzonitrile 
• 73916-08-2 Dimethyl-{4-[(E)-2-(5-methyl-benzooxazol-2-yl)-vinyl]-phenyl}-amine 
• 2583-91-7 4-[(E)-2-(5-Methyl-benzooxazol-2-yl)-vinyl]-benzoic acid methyl ester 
• 436865-50-8 N-(3-hydroperoxy-3-methyl-6-oxocyclohexa-1,4-dienyl)acetamide 
• 1296885-48-7 trifluoromethanesulfonic acid 2-acetylamino-4-methyl-phenyl ester 
• 1296885-51-2 N-[2-(3-hydroxy-3-methyl-but-1-ynyl)-5-methyl-phenyl]-acetamide 
• 1402045-49-1 2-acetamido-4-methylphenyl propyl ether 
• 6962-44-3 N-(2-methoxy-5-methylphenyl)acetamide 
• 93-63-0 2-benzoylamino-4-methyl-phenol 

Relevant academic research and scientific papers

Metabolism and excretion of 2-nitro-p-cresol in rats

Metabolism of 2-nitro-p-cresol (NPC), an important commercial chemical, was studied in female Sprague-Dawley rats, using 14C-NPC. It was found that NPC was rapidly absorbed and excreted after an oral dose of 250 mg/kg. Approximately 90% of the administered dose was excreted into urine and less than 10% of the dose into feces for 5 days. Urinary and fecal excretion were found to the same extent after 48 h. Bile excretion amounted to approximately 25% for 2 days. Blood levels of 14C-NPC reached the maximum concentration (39.4 μg-equivalents/g) within 1 h, and decreased bi-exponentially. The apparent half-lives of 14C-NPC were 3.8 h for the rapid phase and 37 h for the slow phase, respectively. From studying the distribution in organs at 1.5, 6, 24, 72 and 120 h, we found that the concentrations of radioactivity in various tissues of rats were relatively high in the stomach, intestine, liver, kidney, blood, ovary and uterus. Most organs showed the maximum concentrations at 1.5 h, except for intestine, kidney, ovary, and uterus at 6 h. There was no specific tissue retention after 72 h. Two main conjugate metabolites, glucuronide and sulfate of NPC, were detected with free NPC and 2-acetylamino-p-cresol (AAPC) in the urine. NPC was rapidly absorbed and excreted mainly into urine as the conjugate metabolites. A part of NPC was reduced to 2-amino-p-cresol, followed by acetylation to give AAPC.

Antimalarial Benzimidazole Derivatives Incorporating Phenolic Mannich Base Side Chains Inhibit Microtubule and Hemozoin Formation: Structure-Activity Relationship and in Vivo Oral Efficacy Studies

A novel series of antimalarial benzimidazole derivatives incorporating phenolic Mannich base side chains at the C2 position, which possess dual asexual blood and sexual stage activities, is presented. Structure-activity relationship studies revealed that the 1-benzylbenzimidazole analogues possessed submicromolar asexual blood and sexual stage activities in contrast to the 1H-benzimidazole analogues, which were only active against asexual blood stage (ABS) parasites. Further, the former demonstrated microtubule inhibitory activity in ABS parasites but more significantly in stage II/III gametocytes. In addition to being bona fide inhibitors of hemozoin formation, the 1H-benzimidazole analogues also showed inhibitory effects on microtubules. In vivo efficacy studies in Plasmodium berghei-infected mice revealed that the frontrunner compound 41 exhibited high efficacy (98% reduction in parasitemia) when dosed orally at 4 × 50 mg/kg. Generally, the compounds were noncytotoxic to mammalian cells.

Chiral N,N Ligands Enabling Palladium-Catalyzed Enantioselective Intramolecular Heck–Matsuda Carbonylation Reactions by Sequential Migratory and CO Insertions

Unprecedented enantioselective intramolecular Heck carbonylation reactions of arenediazonium salts were enabled by a chiral N,N ligand. This reaction constitutes the first enantioselective Heck carbonylation that proceeds through migratory insertion followed by CO insertion. The enantioenriched functionalized dihydrobenzofurans were obtained in good to high yields and enantiomeric ratios of up to 98:2 under mild and operationally simple reaction conditions.

Cp?Rh(III)/Bicyclic Olefin Cocatalyzed C-H Bond Amidation by Intramolecular Amide Transfer

A bicyclic olefin was discovered as a cocatalyst in a Cp?Rh(III)-catalyzed C-H bond amidation proceeding by an intramolecular amide transfer in N-phenoxyacetamide derivatives. Combining experimental and theoretical studies, we propose that the olefin promotes a Rh(III) intermediate to undergo oxidative addition into the O-N bond to form a Rh(V) nitrenoid species and subsequently direct the nitrenoid to add to the ortho position. The amide directing group plays a dual role as a cleavable coordinating moiety as well as an essential coupling partner for the C-H amidation. This methodology was successfully applied to the late-stage diversification of natural products and a marketed drug under mild conditions.

Production method of 2-acetamido-4-methyl benzene alkyl ether

The invention relates to a production method of 2-acetamido-4-methyl benzene alkyl ether. The production method comprises the following steps of (1) adding o-amino-p-cresol into a reaction still, adding acetic acid for acetylation to obtain o-acetamido-p-cresol; (2) performing detection after reacting for a certain time in the step 1, if a detection result is that ammonia ions exist, then continuously performing the reaction in the step (1); if the reaction result is that the ammonia ions do not exist, then adding sulphate or haloalkane in the reaction still for an alkylation reaction, so as to obtain the 2-acetamido-4-methyl benzene alkyl ether. The production method provided by the invention is simple and easy in obtaining the raw materials, mature in technology, low in cost, less in pollution and high in yield.

Cyclizing radical carboiodination, carbotelluration, and carboaminoxylation of aryl amines

Radical carboiodination of various aryl amines is reported. Aryl diazonium salts, generated in situ from the corresponding aryl amines, are reacted with Bu4NI to provide the corresponding aryl radicals which undergo 5-exo or 6-exo cyclization. Iodine abstraction eventually affords the carboiodinated products in good to excellent yields. If TEMPO is added, the cascade provides the cyclized carboaminoxylation products. Running the reaction in the presence of PhTeTePh affords the phenyltellurated cyclized products.

2-Substituted-2,3-dihydro-1 H -quinolin-4-ones via acid-catalyzed tandem rupe rearrangement-donnelly-farrell ring closure of 2-(3′-hydroxypropynyl) anilines

A range of 2-substituted 2,3-dihydro-1H-quinolin-4-ones have been synthesized from anilines by a two-step process involving Sonogashira coupling with a propargyl alcohol then acid-catalyzed cyclization of the resulting 2-(3′-hydroxypropynyl)anilines. The cyclization reaction appears to proceed via regioselective rearrangement of the propargyl alcohol to an α,β-unsaturated ketone (Rupe rearrangement) and then 6-endo-trig ring closure (Donnelly-Farrell cyclization). The isolation of the α,β-unsaturated ketone intermediate in one example supports this pathway. Georg Thieme Verlag Stuttgart.

Molecular dynamics of cis-1-(2-hydroxy-5-methylphenyl)ethanone oxime and N-(2-hydroxy-4-methylphenyl)acetamide in solution studied by NMR spectroscopy

The formation of hydrogen bonds and molecular dynamics for themolecules cis-1-(2-hydroxy-5-methylphenyl)ethanone oxime (I) and N-(2-hydroxy-4- methylphenyl)acetamide (II) have been investigated in solution using NMR. The results confirm the formation of O-H...O, O-H...N and O...H-N type inter- and intramolecular hydrogen bonds. Spin-lattice relaxation times (T1), activation energy of molecular dynamics and energy of intramolecular hydrogen bonds have been determined. Copyright

Regioselective syntheses of 2- and 4-formylpyrido[2,1-b]benzoxazoles

o-Acetaminophenols (2) reacted with Vilsmeier reagent under Meth-Cohn conditions to yield 2-formylpy-rido[2,l-6]benzoxazoles (5) unexpectedly besides the known compounds 2-(benzoxazol-2′-yl)-3-dimethylaminoacroleins (4). Refluxing 4 in acetic anhydride gave 4-formylpyrido[2,l-6]benzoxazoles (6), an isomer of 5. Both 5a and 6a were structurally characterized by X-ray crystallography. A mechanism for the formation of 5 involving sequential chlorination, dimerization, intramolecular elimination of HC1 to form the oxazole ring, formylation twice, and regioselective intramolecular nucleophilic cyclization to construct the pyridone ring is proposed.

Bisacetamide hydrochloride: A chemoselective and inexpensive N-acetylating reagent for aminophenols

A facile and chemoselective acetylation of aminophenols using bisacetamide hydrochloride under conventional heating and microwave irradiation has been developed. Also, a rapid method for the microwave-assisted preparation of aminophenols is described herein.