2623-33-8

Basic information

• Product Name: N,O-DIACETYL-4-AMINOPHENOL
• Synonyms: (4-acetamidophenyl) ethanoate;acetic acid (4-acetamidophenyl) ester;AcetaMinophen iMpurity (ParacetaMol IMpurity H);N,O-Diacetyl-4-aMinopheno;AcetaMinophen Related CoMpound A;4′-Acetoxyacetanilide (Acetaminophen RCA);4-(Acetylamino)phenyl acetate;4-Acetamidophenyl acetate
• CAS NO: 2623-33-8
• Molecular Formula: C₁₀H₁₁NO₃
• Molecular Weight: 193.2
• EINECS: 220-077-6
• Product Categories: Impurities;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 2623-33-8.mol
• Article Data: 49

Chemical Properties

• Melting Point: 155°C
• Boiling Point: 329.41°C (rough estimate)
• Flash Point: 181.4±23.2 °C
• Appearance: White solid
• Density: 1.2307 (rough estimate)
• Vapor Pressure: 7.27E-06mmHg at 25°C
• Refractive Index: 1.5300 (estimate)
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 14.41±0.70(Predicted)
• Water Solubility: 0.32g/L(25 oC)
• CAS DataBase Reference: N,O-DIACETYL-4-AMINOPHENOL(CAS DataBase Reference)
• NIST Chemistry Reference: N,O-DIACETYL-4-AMINOPHENOL(2623-33-8)
• EPA Substance Registry System: N,O-DIACETYL-4-AMINOPHENOL(2623-33-8)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• Hazardous Substances Data: 2623-33-8(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Different sources of media describe the Uses of 2623-33-8 differently. You can refer to the following data:
1. analgesic, antiinflammatory
2. A synthetic impurity of Acetaminophen

Application

4′-Acetoxyacetanilide may be used as a reference standard for the determination of 4′-acetoxyacetanilide in pharmaceutical formulations by high performance liquid chromatography (HPLC) technique.

General Description

4′-Acetoxyacetanilide is an impurity of Acetaminophen, or Paracetamol as known internationally. This certified solution standard can be used for multiple HPLC applications including pharmaceutical testing, research, and Monograph testing methods. Acetaminophen belongs to a class of drugs called analgesics (pain relievers) and antipyretics (fever reducers).

InChI:InChI=1/C10H11NO3/c1-7(12)11-9-3-5-10(6-4-9)14-8(2)13/h3-6H,1-2H3,(H,11,12)

Upstream product

• 108-24-7 acetic anhydride 
• 123-30-8 4-amino-phenol 
• 51-78-5 p-aminophenol hydrochloride 
• 37441-95-5 1-(2-thioxobenzo[d]oxazol-3(2H)-yl)ethanone 
• 64-17-5 ethanol 
• 64-19-7 acetic acid 
• 622-37-7 Phenyl azide 
• 108-95-2 phenol 
• 41772-21-8 N-phenylthio-1,4-benzoquinone imine 
• 103-90-2 4-acetaminophenol 
• 75-36-5 acetyl chloride 
• 625-56-9 Chloromethyl acetate 
• 13398-12-4 1-(acetoxy)ethyl iodide 
• 103-84-4 Acetanilid 

Downstream Products

• 141-78-6 ethyl acetate 
• 32362-92-8 1-acetoxy-4-(acetyl-nitroso-amino)-benzene 
• 7298-67-1 5-acetamido-2-hydroxyacetophenone 
• 731772-53-5 5-acetoxy-2-acetylamino-1,3-dinitrobenzene 
• 2243-69-8 4-acetamido-3-nitrophenyl acetate 
• 60144-85-6 4'-acetoxy-2'-chloroacetanilide 
• 871894-87-0 N-(4-hydroxy-3,5,6-trinitrophenyl)acetamide 
• 307553-56-6 acetic acid-(2,3,5-trichloro-4-hydroxy-anilide) 
• 857623-82-6 5-acetoxy-2-acetylamino-1,3-dichloro-benzene 
• 408329-12-4 acetic acid-(4-hydroxy-2,3,6-trinitro-anilide) 
• 62-44-2 4-ethoxyacetanilide 
• 103-90-2 4-acetaminophenol 
• 118828-85-6 2,6-dinitro-4-acetylaminophenol 
• 1374606-70-8 4-acetamido-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl acetate 

Relevant articles and documents

Structure of a monoclinic polymorph of N-[4-(acetyloxy)-phenyl]acetamide, a prodrug of acetaminophen

The preparation, single crystal x-ray structure and the computed powder XRD pattern of a monoclinic polymorph of N-[4-(acetyloxy)phenyl]acetamide, a prodrug of acetaminophen, are reported. The polymorph crystallizes in the space group P21/n with Z = 4 and unit cell dimensions a = 7.219(2), b = 8.015(2), c = 16.575(2) A, β = 92.07(1)°, and V = 958.4(4) A3. Infinite spiral molecular arrays result from intermolecular head-to-tail hydrogen bonding between the amidic H atom of one molecule and the acetoxy carbonyl oxygen atom of a 21-related molecule.

Molecules with: O -acetyl group protect protein glycation by acetylating lysine residues

Pharmaceutical intervention for reduction of advanced glycation end products (AGEs) is considered as a therapeutic strategy to attenuate the pathogenesis of diabetes. Many molecules have been reported to possess antiglycation activity, one such example is acetylsalicylic acid (aspirin). It protects proteins from glycation by acetylating the lysine residues. Therefore, in this study we have synthesized and screened molecules containing free N-acetyl, O-acetyl and acetophenone groups. All the selected molecules in this study showed glycation inhibition but interestingly, only molecules with O-acetyl but not N-acetyl and acetophenone groups were capable of acetylating lysine residue. Furthermore, we have demonstrated that pre-acetylation or aspirin treatment prior to the induction of diabetes helps in reducing HbA1c and AGE formation in the streptozotocin induced diabetic mice. Hence pre-acetylation may have an additional therapeutic efficacy of reducing AGE levels in vivo. Incorporation of O-acetyl group into anti-diabetic molecules could be a useful strategy, as it may have an additive effect in reducing AGEs. Identification of such novel acetylating agents represents a new area in the drug discovery process.

Method for diacetate intermediate 5 - acetamide group -2 - (2, 3 - epoxypropoxy) acetophenone

The invention belongs to the field of organic photochemical and drug intermediate chemistry. The invention particularly relates to a method for synthesizing diacetate intermediate - acetamide group 5 - (-2 - 2 epoxypropoxy) acetophenone containing acetylated 3 - photochemical rearrangement reaction in series. The reactant is cooled to the polar organic solvent, Fries rearrangement is carried out directly by ultraviolet - visible light irradiation with specific wavelength, and the intermediate Fries acetyl 2 -4 - acetyl aminophenol is obtained by heating and evaporating the solvent after the reaction is finished. Sodium hydroxide was added to prepare the phenol salt. Then, an intermediate 5 - acetamide group -2 - (2, 3 - epoxypropoxy) acetophenone was obtained by reaction with epichlorohydrin. The tandem type synthesis method disclosed by the invention is simple and feasible, and low-toxicity, high-efficiency and cheap green chemical reagents are used in the synthesis process.

Tin(ii) chloride dihydrate/choline chloride deep eutectic solvent: Redox properties in the fast synthesis of: N -arylacetamides and indolo(pyrrolo)[1,2- a] quinoxalines

In this contribution a physicochemical, IR and Raman characterization for the tin(ii) chloride dihydrate/choline chloride eutectic mixture is reported. The redox properties of this solvent were also studied by cyclic voltammetry finding that it can be successfully used as an electrochemical solvent for electrosynthesis and electroanalytical processes and does not require negative potentials as verified by the reduction of nitrobenzene. The potential use of this eutectic mixture as a redox solvent was further explored in obtaining aromatic amines and N-arylacetamides starting from a wide variety of nitroaromatic compounds. In addition, a fast synthetic strategy for the construction of a series of indolo(pyrrolo)[1,2-a]quinoxalines was developed by reacting 1-(2-nitrophenyl)-1H-indole(pyrrole) with aldehydes. This simple protocol offers a straightforward method for the construction of the target quinoxalines in short reaction times and high yields where the key step involves a tandem one-pot reductive cyclization-oxidation.