39506-61-1

Basic information

• Product Name: 5-Methylsalicylamide
• Synonyms: 5-METHYL SALICYLAMIDE;5-METHYLSALICYAMIDE;Benzamide, 2-hydroxy-5-methyl- (9CI);8023 5-METHYL SALICYLAMIDE;5-Methyl salicylamide ,98%;2-HYDROXY-5-METHYLBENZAMIDE
• CAS NO: 39506-61-1
• Molecular Formula: C₈H₉NO₂
• Molecular Weight: 151.16
• Product Categories: AMIDE;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts
• Mol File: 39506-61-1.mol

Chemical Properties

• Melting Point: 182 °C
• Boiling Point: 278.886 °C at 760 mmHg
• Flash Point: 122.466 °C
• Appearance: /
• Density: 1.231 g/cm³
• Vapor Pressure: 0.002mmHg at 25°C
• Refractive Index: 1.598
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 5-Methylsalicylamide(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Methylsalicylamide(39506-61-1)
• EPA Substance Registry System: 5-Methylsalicylamide(39506-61-1)

Safety Data

• Hazardous Substances Data: 39506-61-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-Methylsalicylamide is used as an intermediate in the synthesis of other organic compounds and pharmaceutical drugs for its anti-inflammatory and analgesic properties. It serves as a potential candidate for the development of new pain-relief medications.
Used in Polymer and Plastics Industry:
5-Methylsalicylamide is used as a stabilizer in the production of certain polymers and plastics, enhancing their stability and performance.

InChI:InChI=1/C8H9NO2/c1-5-2-3-7(10)6(4-5)8(9)11/h2-4,10H,1H3,(H2,9,11)

Upstream product

• 58138-59-3 2-acetoxy-5-methylbenzoyl chloride 
• 1450-72-2 5-methyl-2-hydroxyacetophenone 
• 22717-57-3 methyl 6-hydroxy-m-toluate 
• 34265-58-2 ethyl 5-methylsalicylate 
• 24088-76-4 6-methyl-benzo[e][1,3]oxazine-2,4-dione 

Downstream Products

• 58952-00-4 4-hydroxytoluene-3-thiocarboxylic acid amide 
• 1056954-31-4 2-carbamoyl-4-methylphenyl acetate 
• 165679-42-5 2-(2-Fluoro-phenyl)-6-methyl-benzo[e][1,3]oxazin-4-one 

Relevant articles and documents

Asymmetric Hydrogenation of Cationic Intermediates for the Synthesis of Chiral N,O-Acetals

For over half a century, transition-metal-catalyzed homogeneous hydrogenation has been mainly focused on neutral and readily prepared unsaturated substrates. Although the addition of molecular hydrogen to C=C, C=N, and C=O bonds represents a well-studied paradigm, the asymmetric hydrogenation of cationic species remains an underdeveloped area. In this study, we were seeking a breakthrough in asymmetric hydrogenation, with cationic intermediates as targets, and thereby anticipating applying this powerful tool to the construction of challenging chiral molecules. Under acidic conditions, both N- or O-acetylsalicylamides underwent cyclization to generate cationic intermediates, which were subsequently reduced by an iridium or rhodium hydride complex. The resulting N,O-acetals were synthesized with remarkably high enantioselectivity. This catalytic strategy exhibited high efficiency (turnover number of up to 4400) and high chemoselectivity. Mechanistic studies supported the hypothesis that a cationic intermediate was formed in situ and hydrogenated afterwards. A catalytic cycle has been proposed with hydride transfer from the iridium complex to the cationic sp2 carbon atom being the rate-determining step. A steric map of the catalyst has been created to illustrate the chiral environment, and a quantitative structure–selectivity relationship analysis showed how enantiomeric induction was achieved in this chemical transformation.

Acid Catalyzed Direct-Amidation-Dehydrocyclization of 2-Hydroxy-acetophenones to Benzoxazoles by a One-Pot Sustainable Synthesis

A series of 2-methyl-benzoxazoles have been synthesized starting from 2-hydroxy-acetophenones via a one-pot three steps reaction. Hydroxylamonium salt has been used as amidation agent. The reaction occurs with different anions, but the best results is achieved with hydroxylamonium hydrchloride. Despite the number of consecutive stages, the reaction is highly selective. Mild reaction conditions and various solvents can be used, but trifluoroacetic acid is the preferred. Almost, complete recovery of the trifluoroacetic acid can be achieved by vacuum distillation. The role of trifluoroacetic acid, as well as, of the hydroxylamonium salt suggests a cooperative effect leading to high selective formation of 2-methyl-benzoxazoles. Graphical Abstract: One-pot TFA catalyzed synthesis of benzoxazoles starting from 2-hydroxyacetophenones. (Chemical Equation Presented).

Modulators of Acetyl-Coenzyme A Carboxylase and Methods of Use Thereof

The present invention provides compounds of formula I: along with methods of use of these compounds as pharmaceuticals, particularly in the treatment of obesity, metabolic syndrome, atherosclerosis, cardiovascular disease, insulin resistance, diseases ass

Synthesis and biological activity of novel 1,3-benzoxazine derivatives as K+ channel openers

A new series of 1,3-benzoxazine derivatives with a 2-pyridine 1-oxide group at C4 was designed to explore novel K+ channel openers. Synthesis was carried out by using a palladium(0)-catalyzed carbon-carbon bond formation reaction of imino-triflates with organozinc reagents and via a new one-pot 1,3-benzoxazine skeleton formation reaction of benzoylpyridines. The compounds were tested for vasorelaxant activity in tetraethylammonium chloride (TEA) and BaCl2-induced and high KCl-induced contraction of rat aorta to identify potential K+ channel openers, and also for oral hypotensive effects in spontaneously hypertensive rats. An electron- withdrawing group with the proper shape at C6 and a methyl or halogens group at C7 of the 1,3-benzoxazine nucleus were required for the development of optimal vasorelaxant and hypotensive activity. In particular, 2-(6-bromo-7- chloro-2,2-dimethyl-2H-1,3-benzoxazin-4-yl)pyridine 1-oxide (71) showed more potent vasorelaxant activity (EC50=0.14 μM) against TEA and BaCL2- induced contraction and longer-lasting hypotensive effects than cromakalim (1).