17194-82-0

Basic information

• Product Name: 4-Hydroxyphenylacetamide
• Synonyms: 4-HYDROXYPHENYLACETAMIDE;4-HYDROXYBENZENEACETAMIDE;2-(4-HYDROXYPHENYL)ACETAMIDE;2-(4-HYDROXYPHENYL)-ETHYLAMIDE;LABOTEST-BB LT00848172;ATENOLOL IMP A;ATENOLOL IMPURITY A;P-HYDROXYLPHENYLACETYLAMIDE
• CAS NO: 17194-82-0
• Molecular Formula: C₈H₉NO₂
• Molecular Weight: 151.16
• EINECS: 241-235-0
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Amides;Carbonyl Compounds;Organic Building Blocks;pharmaceutical
• Mol File: 17194-82-0.mol

Chemical Properties

• Melting Point: 176-178 °C(lit.)
• Boiling Point: 273.17°C (rough estimate)
• Flash Point: 198.1 °C
• Appearance: Beige/Fine Crystalline Powder
• Density: 1.2023 (rough estimate)
• Vapor Pressure: 4.22E-07mmHg at 25°C
• Refractive Index: 1.5810 (estimate)
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 9.99±0.26(Predicted)
• Water Solubility: soluble
• BRN: 2085984
• CAS DataBase Reference: 4-Hydroxyphenylacetamide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Hydroxyphenylacetamide(17194-82-0)
• EPA Substance Registry System: 4-Hydroxyphenylacetamide(17194-82-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25-37/39
• WGK Germany: 3
• RTECS: AC3851500
• TSCA: Yes
• Hazardous Substances Data: 17194-82-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
4-Hydroxyphenylacetamide is used as an intermediate for the synthesis of Atenolol (A790075), a widely prescribed medication for treating high blood pressure and angina. It plays a crucial role in the production of this drug, contributing to its effectiveness in managing cardiovascular conditions.
Additionally, 4-Hydroxyphenylacetamide is utilized in the synthesis of various other organic compounds and pharmaceuticals, highlighting its versatility and importance in the pharmaceutical industry.
Used as a Process Impurity:
4-Hydroxyphenylacetamide (Atenolol EP Impurity A) is also recognized as a process impurity for Atenolol (A790075). This means that it is a byproduct or an intermediate formed during the manufacturing process of Atenolol. Understanding and controlling the presence of this impurity is essential for ensuring the quality, safety, and efficacy of the final pharmaceutical product.

InChI:InChI=1/C8H9NO2/c9-8(11)5-6-1-3-7(10)4-2-6/h1-4,10H,5H2,(H2,9,11)

Upstream product

• 300-38-9 3,5-dibromo-L-tyrosine 
• 67-63-0 isopropyl alcohol 
• 99-93-4 4-Hydroxyacetophenone 
• 3233-34-9 methyl 4-hydroxyphenyl acetate 
• 107-31-3 Methyl formate 
• 14191-95-8 4-cyanomethylphenol 
• 623-05-2 (4-hydroxyphenyl)methanol 
• 7339-87-9 4-hydroxyphenylacetaldehyde 
• 156-38-7 4-hydroxyphenylacetate 
• 2491-38-5 2-bromo-1-(4'-hydroxyphenyl)-1-ethanone 
• 182296-61-3 2-bromomethyl-2-(4'-hydroxyphenyl)-1,3-dioxolane 
• 13031-43-1 4-acetyloxyacetophenone 
• 60-18-4 L-tyrosine 
• 300-39-0 3,5-diiodo-l-tyrosine 

Downstream Products

• 29121-31-1 2-(4-Allyloxy-phenyl)-acetamide 
• 29122-69-8 (S)-1-[p-(carbamoylmethyl)phenoxy]-2,3-epoxypropane 
• 115538-83-5 1--3-chloropropan-2-ol 
• 143925-21-7 1--2-acetoxy-3-chloropropane 
• 56715-12-9 (S)-2-(4-(3-chloro-2-hydroxypropoxy)phenyl)acetamide 
• 93379-54-5 (S)-Atenolol 
• 156-38-7 4-hydroxyphenylacetate 
• 84199-13-3 4-benzyloxybenzene-acetamide 
• 1082068-58-3 3-(4-hydroxyyphenyl)-4-(4-thiomethoxyphenyl)-1H-pyrrole-2,5.dione 
• 1446518-69-9 2-(4-(2-(1-acetyl-2-oxocyclohexyl)allyloxy)phenyl)acetamide 
• 868697-76-1 C₃₀H₂₁N₃O₄ 
• 868697-74-9 C₁₇H₁₃NO₄ 
• 868697-75-0 C₁₇H₁₂ClNO₃ 

Relevant articles and documents

A CO2-mediated base catalysis approach for the hydration of triple bonds in ionic liquids

Herein, we report a CO2-mediated base catalysis approach for the activation of triple bonds in ionic liquids (ILs) with anions that can chemically capture CO2 (e.g., azolate, phenolate, and acetate), which can achieve hydration of triple bonds to carbonyl chemicals. It is discovered that the anion-complexed CO2 could abstract one proton from proton resources (e.g., IL cation) and transfer it to the CN or CC bonds via a six-membered ring transition state, thus realizing their hydration. In particular, tetrabutylphosphonium 2-hydroxypyridine shows high efficiency for hydration of nitriles and CC bond-containing compounds under a CO2 atmosphere, affording a series of carbonyl compounds in excellent yields. This catalytic protocol is simple, green, and highly efficient and opens a new way to access carbonyl compounds via triple bond hydration under mild and metal-free conditions.

Ti-superoxide catalyzed oxidative amidation of aldehydes with saccharin as nitrogen source: Synthesis of primary amides

A new heterogeneous catalytic system (Ti-superoxide/saccharin/TBHP) has been developed that efficiently catalyzes oxidative amidation of aldehydes to produce various primary amides. The protocol employs saccharin as amine source and was found to tolerate a wide range of substrates with different functional groups. Moderate to excellent yields, catalyst reusability and operational simplicity are the main highlights. A possible mechanism and the role of the catalyst in oxidative amidation have also been discussed.

Production method of p-hydroxyphenylacetamide

The invention relates to a production method of p-hydroxyphenylacetamide and belongs to the medicine field. Phenol and glyoxylic acid are taken as raw materials to be prepared into a competitive product via processes of synthesis, reduction and ammonolysis. The production method has the advantages that the optimal synthesis process is determined, yield of the obtained p-hydroxyphenylacetamide can reach over 80%, purity can reach more than 99%, and the technical process is simpler, easy to implement and environment friendly.

Synthesis and PGE2 production inhibition of 1H-furan-2,5-dione and 1H-pyrrole-2,5-dione derivatives

3,4-Diphenyl-substituted 1H-furan-2,5-dione and 1H-pyrrole-2,5-dione derivatives were synthesized and evaluated for the inhibitory activities on LPS-induced PGE2 production in RAW 264.7 macrophage cells. Both 1H-furan-2,5-dione and 1H-pyrrole-2,5-dione rings as main scaffolds were easily obtained using one of three synthetic methods. Among the compounds investigated, 1H-3-(4-sulfamoylphenyl)-4-phenyl-pyrrole-2,5-dione (6l) showed a strong inhibitory activity (IC50 = 0.61 μM) of PGE2 production.

Isolation and production of catalytic antibodies using phage technology

Disclosed and claimed are methods for producing catalytic antibodies, including human catalytic antibodies, from bacteriophage. The methods require the cloning, selection, screening, and isolation of catalytic antibodies. Also disclosed and claimed are the products themselves, the catalytic antibodies, made from the phage technology. In addition, catalytic antibodies produced from the phage technology and useful in prodrug activation are disclosed and claimed. And finally, the invention also understands the production of catalytic antibodies to phosphonates.

A synthesis of atenolol using a nitrile hydration catalyst

The synthesis of atenolol is described using a platinum containing homogeneous catalyst for the conversion of a nitrile to an amide. The catalytic reaction may be employed as the final step in the synthesis or in the preparation of the intermediate 4-hydroxyphenylacetamide. The structure of the nitrile intermediate, 1-(4′-cyanomethylphenoxy)-2-hydroxy-3-isopropylaminopropane, has been determined by X-ray crystallography.

Facile 1,2-aryl migration of 2-halomethyl-2-(4'-hydroxyphenyl) ketals: A novel single step synthesis of 4-hydroxyphenylacetic acid and its derivatives

1,2-Aryl migration of 1-halomethyl-2-(4-hydroxyphenyl) ketals, obtained from 2-bromomethyl 4-hydroxyacetophenone, under mild basic conditions have been shown to give 4-hydroxyphenylacetic acid or its derivatives which are key intermediates in the preparation of Atenolol, a well known cardiac β-blocker.

Electronic Substituent Effects in the Nitrilase-Catalyzed Hydrolysis of Para-Substituted Benzyl Cyanides

The initial rates of the nitrilase (Novo)-catalyzed hydrolysis of a series of para-substituted benzyl cyanides (R = NO2, Cl, OCH3, OH, NH2) were found to be susceptible to the nature of the para-substituent of the substrate and a Hammett-type linear free energy correlation was observed with ρ = 0.96.In a separate study, effective solubilization of substituted benzyl cyanide substrates having electron-donating groups (OH, NH2, OCH3) was achieved upon mixing with β-cyclodextrin to form 1:1 mol ratio inclusion complexes, but para-substituted benzyl cyanides with electron-withdrawing groups (Cl, NO2) were not fully solubilized under the same conditions.In addition, it was shown that the presence of β-cyclodextrin not only had no inhibitory effect on the enzyme activity, but it actually increased the initial rate of hydrolysis of the unsubstituted benzyl cyanide:β-cyclodextrin inclusion complex.However, the initial rates of hydrolysis were observed to be smaller when β-cyclodextrin was added to the para-substituted benzyl cyanides.

Preparation of aromatic acetamides from aryl methyl ketones

A method is provided for preparing aromatic acetamides comprising reacting an aryl methyl ketone containing the same number of carbon atoms as the aromatic acetamide, with sulfur and ammonia under substantially anhydrous conditions. The method is particularly useful for the preparation of 4-hydroxyphenylacetamide from 4-hydroxyacetophenone.