27642-27-9

Basic information

• Product Name: Benzamide, 4-hydroxy-N-methyl- (9CI)
• Synonyms: Benzamide, 4-hydroxy-N-methyl- (9CI);N-Methyl 4-hydroxy benzamide
• CAS NO: 27642-27-9
• Molecular Formula: C₈H₉NO₂
• Molecular Weight: 151.16256
• Product Categories: AMIDE
• Mol File: 27642-27-9.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 359.9°Cat760mmHg
• Flash Point: 171.4°C
• Appearance: /
• Density: 1.179g/cm³
• Vapor Pressure: 1.11E-05mmHg at 25°C
• Refractive Index: 1.564
• Storage Temp.: 2-8°C
• CAS DataBase Reference: Benzamide, 4-hydroxy-N-methyl- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Benzamide, 4-hydroxy-N-methyl- (9CI)(27642-27-9)
• EPA Substance Registry System: Benzamide, 4-hydroxy-N-methyl- (9CI)(27642-27-9)

Safety Data

• Hazardous Substances Data: 27642-27-9(Hazardous Substances Data)

Usage

Uses

4-Hydroxy-N-methylbenzamide is a useful building block.

InChI:InChI=1/C8H9NO2/c1-9-8(11)6-2-4-7(10)5-3-6/h2-5,10H,1H3,(H,9,11)

Upstream product

• 120-47-8 Ethyl 4-hydroxybenzoate 
• 74-89-5 methylamine 
• 99-93-4 4-Hydroxyacetophenone 
• 34523-34-7 4-hydroxyacetophenone oxime 
• 96-31-1 N,N'-Dimethylurea 
• 99-96-7 4-hydroxy-benzoic acid 
• 27914-73-4 4-acetoxybenzoyl chloride 
• 28141-24-4 4-hydroxybenzoyl chloride 
• 99-76-3 methyl 4-hydroxylbenzoate 

Downstream Products

• 34523-34-7 4-hydroxyacetophenone oxime 
• 99-96-7 4-hydroxy-benzoic acid 
• 1421923-05-8 4-{[2-(2,5-dimethyl-4-nitrobenzyl)-1,3-thiazol-4-yl]methoxy}-N-methylbenzamide 
• 1332720-02-1 C₂₀H₁₈F₃N₅O₃ 
• 1190089-98-5 C₂₃H₂₇N₃O₄ 
• 41123-33-5 Thiophosphoric acid O-ethyl ester O'-(4-methylcarbamoyl-phenyl) ester S-propyl ester 

Relevant articles and documents

Acid hydrolysis of amides obtained by Beckmann rearrangement of methyl ketones oximes of unsaturated γ-lactone, aromatic, and alicyclic series

Beckmann rearrangement was performed of oximes of substituted 3-acetyl-4-methyl-5,5-dimethyl(pentamethylene)-2-oxo-2,5-dihydrofuranes in the presence of boron trifluoride etherate. Aiming at establishing the spatial arrangement of the oximes the hydrolysis was carried out of acid amides obtained by Beckmann rearrangement of oximes of methyl ketones belonging to unsaturated γ-lactone series and also to aromatic and alicyclic series. The hydrolysis with 20% sulfuric acid led to the formation of the corresponding acid and amine, and the hydrolysis with acetic and hydrochloric acids resulted in retrobeckmann rearrangement giving the initial oximes.

Preparation method of N-methyl-4-hydroxybenzamide

The invention relates to a preparation method of N-methyl-4-hydroxybenzamide, wherein the preparation method comprises the following steps: 1) adding 4-hydroxybenzoyl chloride and triethylamine into a container, heating under stirring to make the system temperature be 20-50 DEG C, then dropping absolute ethyl alcohol with the dropping time of 0.5-1 h, after the dropping is finished, carrying out a heat preservation reaction for 2-5 h at the temperature of 20-50 DEG C, then carrying out suction filtration of the reaction liquid to remove triethylamine hydrochloride, and thus obtaining a filtrate, namely ethyl 4-hydroxybenzoate; and 2) adding ethyl 4-hydroxybenzoate into the container, stirring and heating to 30-60 DEG C, dropping methylamine with the dropping time of 0.5-1 h, after the dropping is finished, carrying out a heat preservation reaction for 3-5 h at the temperature of 30-60 DEG C, cooling to room temperature, precipitating out a large number of solids, and carrying out suction filtration, to obtain a filter cake, namely N-methyl-4-hydroxybenzamide. Compared with the prior art, with adopting of the stepwise reaction, the yield of N-methyl-4-hydroxybenzamide is greatly improved.

On the intractability of estrogen-related receptor α as a target for activation by small molecules

The estrogen-related receptor α (ERRα) is a potential target for activation in the treatment of metabolic disease. To date, no small-molecule agonists of ERRα have been identified despite several high-throughput screening campaigns. We describe the synthesis and profiling of a small array of compounds designed on the basis of a previously reported agonist-bound crystal structure of the closely related receptor ERRγ. The results suggest that ERRα may be intractable as a direct target for pharmacologic activation.