3556-86-3

Basic information

• Product Name: METHYL 3-HYDROXY-4-METHYLBENZOATE
• Synonyms: METHYL 3-HYDROXY-4-METHYLBENZOATE;3-HYDROXY-4-METHYLBENZOIC ACID METHYL ESTER;3-HYDROXY-P-TOLUIC ACID METHYL ESTER;3,4-Cresotic acid methyl ester;benzoic acid, 3-hydroxy-4-methyl-, methyl ester;Methyl 4-Methyl-3-hydroxybenzoate
• CAS NO: 3556-86-3
• Molecular Formula: C₉H₁₀O₃
• Molecular Weight: 166.17
• Product Categories: Esters;Phenyls & Phenyl-Het
• Mol File: 3556-86-3.mol
• Article Data: 25

Chemical Properties

• Melting Point: 119.0-120.5 °C
• Boiling Point: 294.6 °C at 760 mmHg
• Flash Point: 128.9 °C
• Appearance: /
• Density: 1.169 g/cm³
• Vapor Pressure: 1.41E-05mmHg at 25°C
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility: Acetone (Slightly), Chloroform (Slightly)
• PKA: 9.50±0.10(Predicted)
• CAS DataBase Reference: METHYL 3-HYDROXY-4-METHYLBENZOATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 3-HYDROXY-4-METHYLBENZOATE(3556-86-3)
• EPA Substance Registry System: METHYL 3-HYDROXY-4-METHYLBENZOATE(3556-86-3)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 3556-86-3(Hazardous Substances Data)

Usage

Synthesis

Methyl 3-hydroxy-4-methylbenzoate is synthesized by the following steps:The amino ester 35 (60 g, 0.364 mol) was added to dil. H2SO4 (125 ml ?conc. H2SO4 diluted with 1 L water) and warmed on a water bath until all ?the compound was dissolved. Cold water (800 ml) was added and the ?mixture was cooled to 0 °C. NaNO2 (62.6 g, 0.907 mol) was added to this ?mixture with constant stirring. It was then stirred at room temperature for 15 minutes. ?Then, urea (65.4 g, 1.09 mol) was added in portions. The mixture was warmed at 50 oC for ?15 minutes (temperature was not allowed to rise above 55 oC). EtOAc was added to the?reaction mixture and washed with brine, dried (anhydrous Na2SO4), filtered and ?concentrated under reduced pressure to afford a colourless solid (26.56 g).

Uses

Methyl 4-Methyl-3-hydroxybenzoate is used in the preparation of potent antimalarial agents. Also used in the preparation of aromatic inhibtors of anthranilate synthase.

InChI:InChI=1/C8H8O3/c1-5-2-3-6(8(10)11)4-7(5)9/h2-4,9H,1H3,(H,10,11)/p-1

Upstream product

• 99-75-2 4-methyl-benzoic acid methyl ester 
• 18595-18-1 3-amino-4-methyl benzoic acid methyl ester 
• 3556-83-0 methyl 4-methyl-3-methoxybenzoate 
• 67-56-1 methanol 
• 19438-10-9 methyl 3-hydroxybenzoate 
• 186581-53-3 diazomethane 
• 586-30-1 3-hydroxy-4-methylbenzoic acid 
• 118446-42-7 3-methoxycarbonylhepta-3,5-dienoic acid 

Downstream Products

• 869892-67-1 3-(1-methoxycarbonyl-ethoxy)-4-methylbenzoic acid methyl ester 
• 159640-54-7 methyl 4-methyl-3-trifluoromethanesulfonyloxybenzoate 
• 895240-72-9 3-(3-methoxy-propoxy)-4-methyl-benzoic acid methyl ester 
• 865138-66-5 methyl 3-isopropoxy-4-methylbenzoate 
• 87808-14-8 4-methyl-3-hydroxyethylbenzoate 
• 87808-27-3 Methyl 2-bromo-5-hydroxy-4-methylbenzoate 
• 886858-77-1 methyl 3-(difluoromethoxy)-4-methylbenzoate 
• 220504-68-7 methyl 3-acetyloxy-4-(bromomethyl)benzoate 

Relevant articles and documents

Iron-catalyzed arene C-H hydroxylation

The sustainable, undirected, and selective catalytic hydroxylation of arenes remains an ongoing research challenge because of the relative inertness of aryl carbon-hydrogen bonds, the higher reactivity of the phenolic products leading to over-oxidized by-products, and the frequently insufficient regioselectivity. We report that iron coordinated by a bioinspired L-cystine-derived ligand can catalyze undirected arene carbon-hydrogen hydroxylation with hydrogen peroxide as the terminal oxidant. The reaction is distinguished by its broad substrate scope, excellent selectivity, and good yields, and it showcases compatibility with oxidation-sensitive functional groups, such as alcohols, polyphenols, aldehydes, and even a boronic acid. This method is well suited for the synthesis of polyphenols through multiple carbon-hydrogen hydroxylations, as well as the late-stage functionalization of natural products and drug molecules.

A convenient synthesis of phenols

Anilines are rapidly, often within 60 minutes, converted into the corresponding phenols in up to 87% isolated yield. The presented experimentally simple protocol display broad compatibility with a variety of functional groups, and in particular, well suited for the preparation of methyl-substituted phenols. Such phenols are not easily available by other synthetic approaches. The formation of phenolic radical coupling products was not observed even for activated anilines using this open flask method.

NOVEL INHIBITORS OF MAP4K1

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