613-84-3

Usage

Uses

Used in Pharmaceutical Industry:
5-Methylsalicylaldehyde is used as a key intermediate in the synthesis of novel 2-Phenylcyclopropanamine derivatives. These derivatives serve as Lysine-specific Demethylase 1 inhibitors (LSD1-inhibitors), which are of significant interest in the prevention or treatment of primary brain tumors. By targeting LSD1, these inhibitors can potentially regulate gene expression and cellular processes, offering a promising therapeutic approach for brain cancer treatment.

InChI:InChI=1/C8H8O2/c1-6-2-3-8(10)7(4-6)5-9/h2-5,10H,1H3

Upstream product

• 50-00-0 formaldehyd 
• 106-44-5 p-cresol 
• 302-17-0 chloral hydrate 
• 74-90-8 hydrogen cyanide 
• 67-66-3 chloroform 
• 4383-07-7 2-hydroxymethyl-4-methylphenol 
• 89-56-5 5-Methylsalicylic acid 
• 100-97-0 hexamethylenetetramine 
• 298-12-4 Glyoxilic acid 
• 76-03-9 trichloroacetic acid 
• 98017-53-9 4-<2-Hydroxy-5-methyl-phenyl>-3-methyl-but-3-en-saeure-(1)-methylester 
• 22068-59-3 2-(1,3-dithiolan-2-yl)-p-cresol 
• 130332-98-8 5-Methyl-2-(2-trimethylsilanyl-ethoxymethoxy)-benzaldehyde 
• 55359-68-7 2-(methoxymethoxy)-5-methylbenzaldehyde 

Downstream Products

• 106052-71-5 2-hydroxy-5-methyl-benzaldehyde-[2]pyridylimine 
• 452-86-8 4-methyl-1,2-dihydroxybenzene 
• 23000-31-9 6-methyl-3-phenylcoumarin 
• 192819-68-4 3-chloromethyl-5-methylsalicylaldehyde 
• 61313-36-8 5'-chloro-2,2'-dihydroxy-5-methyl-trans-chalcone 
• 10242-13-4 6-methyl-2-oxo-2H-chromene-3-carboxylic acid 
• 25871-52-7 5-methyl-2-phenylbenzofuran 
• 66620-31-3 2-hydroxy-5-methyl-3-nitro-benzaldehyde 
• 4383-07-7 2-hydroxymethyl-4-methylphenol 
• 89-56-5 5-Methylsalicylic acid 
• 2432-18-0 2,6-diiodo-4-methylphenol 
• 33172-54-2 3-bromo-2-hydroxy-5-methylbenzaldehyde 

Relevant academic research and scientific papers

Enantioselective Hydroboration of Ketones Catalyzed by Rare-Earth-Metal Complexes Supported with Phenoxy-Functionalized TsDPEN Ligands

Six novel chiral rare-earth-metal complexes bearing the phenoxy-functionalized TsDPEN ligand H3L1 (H3L1 = N-((1R,2R)-2-((3,5-di-Tert-butyl-2-hydroxybenzyl)amino)-1,2-diphenylethyl)-4-methylbenzenesulfonamide) were synthesized successfully and well characterized. The solid-state structures of four tetranuclear rare-earth-metal complexes [RE2L13]2 (RE = Nd (1), Sm (2), Eu (3), Gd (4)) and the dual-core yttrium complex Y2L13 (5) were determined by X-ray diffraction, respectively. The structure of lanthanum complex 6 was speculated by the 1H DOSY spectroscopy in THF-d8 together with DFT calculations. Complexes 1-5 were employed to catalyze the enantioselective hydroboration of ketones and α,β-unsaturated ketones using pinacolborane (HBpin) as a reductant, and complex 1 gave better outcomes in comparison to the others. The corresponding secondary alcohols were obtained in excellent yields and moderate ee values. The same results were also achieved using the combined catalyst system of the neodymium amide Nd[N(SiMe3)2]3 with the phenoxy-functionalized TsDPEN ligand H3L1 in a 1:1.5 molar ratio.

Phosphine-catalyzed sequential (2+3)/(2+4) annulation of γ-vinyl allenoates: Access to the synthesis of chromeno[4,3-: B] pyrroles

A phosphine-catalyzed cascade (2+3)/(2+4) cyclization reaction of γ-vinyl allenoates with aldimine esters has been developed to provide a series of chromeno[4,3-b]pyrrole derivatives that contain three contiguous stereogenic centers. The method gives a good yield, excellent chemoselectivity and diastereoselectivity under mild conditions.

Highly efficient and practical aerobic oxidation of alcohols by inorganic-ligand supported copper catalysis

The oxidation of alcohols to aldehydes or ketones is a highly relevant conversion for the pharmaceutical and fine-chemical industries, and for biomass conversion, and is commonly performed using stoichiometric amounts of highly hazardous oxidants. The aerobic oxidation of alcohols with transition metal complex catalysts previously required complicated organic ligands and/or nitroxyl radicals as co-catalysts. Herein, we report an efficient and eco-friendly method to promote the aerobic oxidation of alcohols using an inorganic-ligand supported copper catalyst 1, (NH4)4[CuMo6O18(OH)6], with O2 (1 atm) as the sole oxidant. Catalyst 1 is synthesized directly from cheap and commonly available (NH4)6Mo7O24·4H2O and CuSO4, which consists of a pure inorganic framework built from a central CuII core supported by six MoVIO6 inorganic scaffolds. The copper catalyst 1 exhibits excellent selectivity and activity towards a wide range of substrates in the catalytic oxidation of alcohols, and can avoid the use of toxic oxidants, nitroxyl radicals, and potentially air/moisture sensitive and complicated organic ligands that are not commercially available. Owing to its robust inorganic framework, catalyst 1 shows good stability and reusability, and the catalytic oxidation of alcohols with catalyst 1 could be readily scaled up to gram scale with little loss of catalytic activity, demonstrating great potential of the inorganic-ligand supported Cu catalysts in catalytic chemical transformations.

MgBr2 supported on Fe3O4@SiO2?~?urea nanoparticle: An efficient catalyst for ortho-formylation of phenols and oxidation of benzylic alcohols

Urea was successfully immobilized on the surface of chloropropyl-modified Fe3O4@SiO2 core–shell magnetic nanoparticles, then supported by MgBr2 and acts as a unique catalyst for oxidation of benzylic alcohols to aldehydes and ketones, and ortho-formylation of phenols to salicylaldehydes. The prepared catalyst was characterized by FT-IR, transmission electron microscopy, scanning electron microscopy, X-ray powder diffraction, dispersive X-ray spectroscopy, CHN and TGA. It was found that Fe3O4@SiO2?~?urea/MgBr2 showed higher catalytic activity than homogenous MgBr2, and could be reused several times without significant loss of activity.

Efficient microwave-assisted regioselective one pot direct: Ortho -formylation of phenol derivatives in the presence of nanocrystalline MgO as a solid base catalyst under solvent-free conditions

In this research, at first nanocrystalline MgO was prepared and then the solvent-free reactions of phenol derivatives with paraformaldehyde in the presence of the obtained nanocrystalline MgO as a new catalyst under microwave irradiation were investigated. In this reaction, ortho-hydroxyaromatic aldehydes were yielded as products. This method seems to be comparable with other reported methods due to its high yield and regioselectivity. The significant features of this method are short reaction times, high yields, and easy and quick isolation of the products.

Synthesis of Monofunctionalized Calix[5]arenes

Seven OH-free and O -permethylated monofunctionalized calix[5]arenes carrying either additional methyl or tert -butyl groups are prepared following fragment condensation protocols. This strategy proves to be superior to previous approaches. Calix[5]arenes with free OH groups all adopt a cone conformation stabilized by a seam of hydrogen bonds at the lower rim. Post-condensation modifications, i.e., methylation of phenolic OH groups or functional group interconversions can also be achieved. Bulky tert -butyl groups are also found to stabilize the cone conformations of O -methylated compounds. These compounds offer versatile functional groups that make these concave molecules interesting building blocks for the synthesis of more sophisticated molecular architectures.

One-Pot Synthesis of Functionalized Fused Furans via a BODIPY-Catalyzed Domino Photooxygenation

Six-membered ring fused furans containing a tetrasubstituted tertiary carbon were prepared in an unprecedented one-pot BODIPY-catalyzed domino photooxygenation/reduction process. A series of functionalized furans was synthesized from readily available 2-alkenylphenols and mechanistic studies were performed to account for the domino photosensitized oxygenation.

Enantioselective Construction of Tetrahydroquinazoline Motifs via Palladium-Catalyzed [4 + 2] Cycloaddition of Vinyl Benzoxazinones with Sulfamate-Derived Cyclic Imines

A palladium-catalyzed enantioselective [4 + 2] cycloaddition reaction of vinyl benzoxazinones with sulfamate-derived cyclic imines is described, affording the tetrahydroquinazolines bearing several functional rings in high yields (up to 99% yield) with good to excellent diastereoselectivities and excellent enantioselectivities (up to 96% ee). This reaction represents the first Pd-catalyzed asymmetric decarboxylative cycloaddition of vinyl benzoxazinones with imines.

Highly practical and efficient preparation of aldehydes and ketones from aerobic oxidation of alcohols with an inorganic-ligand supported iodine catalyst

Herein, we divulge an efficient protocol for aerobic oxidation of alcohols with an inorganic-ligand supported iodine catalyst, (NH4)5[IMo6O24]. The catalyst system is compatible with a wide range of groups and exhibits high selectivity, and shows excellent stability and reusability, thus serving as a potentially greener alternative to the classical transformations.

In Vitro Antitumor Activity of Newly Synthesized Pyridazin-3(2H)-One Derivatives via Apoptosis Induction

Systemic toxicity associated with drug resistance continues to be the major obstacle to curative therapy of cancer. Tumor cell resistance to chemotherapeutic drugs often results in coordinate resistance to other structurally and functionally unrelated drugs and the subsequent development of cross resistance phenotype. Therefore, it seems necessary to identify new molecules as anticancer agents. In this process, we synthesized a series of new pyridazin-3(2H)-one derivatives and evaluated their antitumor potential. These cyclic molecules were synthesized and designed as a combination of benzofuran with pyridazinones. All final compounds have been characterized by spectral and elemental analyses to confirm successful synthesis reactions. To evaluate their anticancer activity, all derivatives were assessed against the human breast adenocarcinoma cell line (MCF-7) and the murine mastocytoma cell line (P815) using the methyl tetrazolium Test (MTT assay). The cytotoxic activity was found to be dose-dependent and the IC50 values of the synthesized compounds ranged from 14.5 to 40 μM against MCF-7 and from 35 to 82.5 μM against P815. At the same time, no cytotoxic activity was observed against normal cells. In order to investigate the molecular mechanism of the most cytotoxic product (6f), apoptosis induction was measured against MCF-7 cells. Using the annexin-V FITC staining technique, we showed that the cytotoxic effect of this product is associated with apoptosis induction.