2150-41-6

Usage

Uses

Used in Chemical Synthesis:
METHYL 2,4-DIMETHOXYBENZOATE is used as a key intermediate in the synthesis of 1,5-diaryl-1,3,5-pentanetriones, which are important compounds in the field of organic chemistry.
Used in Agriculture:
METHYL 2,4-DIMETHOXYBENZOATE is used as an antifeedant in agriculture for protecting planted seedlings in the field. Its high antifeedant index makes it an effective candidate for deterring pests and ensuring the healthy growth of crops.

InChI:InChI=1/C10H12O4/c1-12-7-4-5-8(10(11)14-3)9(6-7)13-2/h4-6H,1-3H3

Upstream product

• 89-86-1 4-hydroxysalicylic acid 
• 77-78-1 dimethyl sulfate 
• 5446-02-6 4-methoxymethylsalicylate 
• 74-88-4 methyl iodide 
• 186581-53-3 diazomethane 
• 91-52-1 2,4 dimethoxybenzoic acid 
• 865-33-8 potassium methanolate 
• 106614-28-2 methyl 2,4-difluorobenzoate 
• 124-41-4 sodium methylate 
• 75-91-2 tert.-butylhydroperoxide 
• 613-45-6 2,4-Dimethoxybenzaldehyde 
• 7314-44-5 2,4-dimethoxylbenzyl alcohol 
• 3186-53-6 O-methyl S-p-methylphenyl thiocarbonate 
• 133730-34-4 2,4-dimethoxyphenylboronic acid 

Downstream Products

• 132593-11-4 3-(2,4-dimethoxy-phenyl)-2-(2-methoxy-phenyl)-3-oxo-propionitrile 
• 94312-76-2 2,3-bis-(2,4-dimethoxy-phenyl)-3-oxo-propionitrile 
• 76832-37-6 2,4,2’,4’,2”,4”-hexamethoxytriphenylcarbinol 
• 91-52-1 2,4 dimethoxybenzoic acid 
• 132593-12-5 3-(2,4-dimethoxyphenyl)-2-(4-methoxyphenyl)-3-oxopropanenitrile 
• 76569-43-2 2,4-dimethoxybenzoylacetonitrile 
• 198351-03-0 8-Allyl-2-(2,4-dimethoxy-phenyl)-chromen-4-one 
• 66284-46-6 Hydroxy-diphenyl-(2,4-dimethoxy-phenyl)-methan 
• 134937-23-8 2-(2',4'-Dimethoxyphenyl)-6-hydroxybenzofuran 
• 39604-64-3 1-(2-hydroxy-4-methoxyphenyl)-2-(4-methoxyphenyl)ethanone 
• 18440-00-1 2-Hydroxy-4-methoxyphenyl 2-methoxybenzyl ketone 
• 18439-96-8 1-(2-hydroxy-4-methoxyphenyl)-2-phenylethanone 
• 111798-01-7 3-(2,4-dimethoxy-phenyl)-2-(2-methoxy-phenyl)-3-oxo-propionic acid ethyl ester 
• 102172-23-6 3-(2,4-dimethoxy-phenyl)-3-oxo-2-phenyl-propionic acid ethyl ester 

Relevant academic research and scientific papers

Radical-capturing reaction of 5,7,3′,4′-tetramethylquercetin with the AIBN radical initiator

In order to clarify the mechanism for the radical-capturing reaction which is initiated at the C3-hydroxyl group of flavonols, 5,7,3′,4′-tetramethylquercetin (TMQ) was reacted with the 2,2′-azobis-isobutyronitrile (AIBN) radical initiator in benzene. Six products, one depside and its two hydrolytic products, one nitrite adduct, and two others, were isolated from the reaction mixture, and their structures were determined by instrumental analyses. The quantitative change to the four main products against the reaction time was measured by an HPLC method. The radical-capturing reaction pathway for TMQ with AIBN is proposed from these products and their quantitative changes. The pathway dividing into two clearly reveals that one subpath formed the depside and its hydrolytic products, while the other formed the nitrite adduct. The reactivity of each two sub-path was nearly the same, different from the case of TMQ and the 2,2′-azobis-2,4-dimethylvaleronitrile (AMVN) radical initiator.

Synthesis, Antiproliferative and Antioxidant Activity of 3-Mercapto-1,2,4-Triazole Derivatives as Combretastatin A-4 Analogues

Two series of 3-mercapto-1,2,4-triazole derivatives containing alkoxy substituents different in size and position were synthesized and their structures were characterized by FT-IR, 1H NMR, 13C NMR spectroscopy and elemental analysis. The synthesized compounds were assessed for their antiproliferative activity against colon cancer cell line (SW480). The results indicated that the size and position of the alkoxy group significantly influenced the antiproliferative activity. The highest cancer cell growth inhibition values were observed for the compounds containing 3,4,5-trimethoxyphenyl groups in their structures (57.74, 54.14 and 60.70% at 50 μM for compounds 5a, 12b and 14, respectively). The synthesized compounds were also subjected to DPPH protocol for evaluating the antioxidant activity. The results showed that all compounds had moderate to high levels of antioxidant capacity as compared to ascorbic acid as standard, the highest free radical scavenging capacity of 75% was observed for compound 4a at 50 μM.

Synthesis of acyclic and cyclic phosphonates based on substituted 2-hydroxybenzylic alcohols

A convenient synthesis of benzylic phosphonates and 2,3-dihydrobenzo[d][1,2]oxaphosphole 2-oxides substituted at the aromatic ring, as well as their precursors, 2-hydroxybenzylic alcohols, from the derivatives of salicylic aldehyde, salicylic acid, and 2-hydroxyacetophenone bearing an additional hydroxy or methoxy group at the para position of the aromatic ring was developed. For the first time, the possibility of selective demethylation of the methoxy group positioned ortho to the methylene phosphonate fragment with retention of the methoxy group at the para position was shown.

Palladium-Catalyzed, Copper(I)-Promoted Methoxycarbonylation of Arylboronic Acids with O-Methyl S-Aryl Thiocarbonates

Here, we report O-methyl S-aryl thiocarbonates as a versatile esterification reagent for palladium-catalyzed methoxycarbonylation of arylboronic acid in the presence of copper(I) thiophene-2-carboxylate (CuTC). The reaction condition is mild, and a variety of substituents including sensitive-Cl,-Br, and free-NH2 could be tolerated. Further applications in the late-stage esterification of some pharmaceutical drugs demonstrate the broad utility of this method.

Electrochemical C-H cyanation of electron-rich (Hetero)arenes

A straightforward method for the electrochemical C-H cyanation of arenes and heteroarenes that proceeds at room temperature in MeOH, with NaCN as the reagent in a simple, open, undivided electrochemical cell is reported. The platinum electrodes are passivated by ad-sorbed cyanide, which allows conversion of an exceptionally broad range of electron-rich substrates all the way down to dialkyl arenes. The cyanide electrolyte can be replenished with HCN, opening opportunities for salt-free industrial C-H cyanation.

Phosphite-catalyzed alkoxycarbonylation of aryl diazonium salts

In this communication, an interesting phosphite-catalyzed alkoxycarbonylation of aryl diazonium salts has been reported. At room temperature and under CO pressure, moderate to good yields of the desired esters can be produced in the absence of bases or an

Methylation of Aliphatic and Aromatic Carboxylic Acids with Dimethyl Carbonate under the Influence of Manganese and Iron Carbonyls

The synthesis of methyl esters has been carried out via the reaction of aliphatic and aromatic carboxylic acids with dimethyl carbonate in the presence of manganese and iron carbonyls. The optimal ratio of catalyst and reagents and other conditions for the synthesis of methyl esters of carboxylic acids with high yield have been found.

Rational Design of Rod-Like Liquid Crystals Exhibiting Two Nematic Phases

Recently, a polar, rod-like liquid-crystalline material was reported to exhibit two distinct nematic mesophases (termed N and NX) separated by a weakly first-order transition. Herein, we present our initial studies into the structure–property relationships that underpin the occurrence of the lower-temperature nematic phase, and report several new materials that exhibit this same transformation. We have prepared material with significantly enhanced temperature ranges, allowing us to perform a detailed study of both the upper- and lower-temperature nematic phases by using small-angle X-ray scattering. We observed a continuous change in d spacing rather than a sharp change at the phase transition, a result consistent with a transition between two nematic phases, structures of which are presumably degenerate.

Microwave-assisted methylation of dihydroxybenzene derivatives with dimethyl carbonate

Using a focused microwave reactor, methylation with dimethyl carbonate (DMC) of 1,2- and 1,4-dihydroxybenzene derivatives, found in the product spectrum of lignin depolymerisation, leads to the respective aromatic bis-methyl ethers with excellent isolated yields. Stoichiometric as well as catalytic amounts of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) are effective for the bis-methylation of these dihydroxybenzenes at relatively mild temperatures (160-190 °C). Conversion of resorcinol (1,3-dihydroxybenzene) under similar conditions leads to a mixture of 1,3-dimethoxybenzene and methyl 2,4-dimethoxybenzoate. The unusual reactivity of resorcinol's phenyl ring towards DMC can be explained by the synergic effect of its two strongly activating ortho/para directing groups.

Nitrogen enriched mesoporous organic polymer anchored copper(ii) material: An efficient and reusable catalyst for the synthesis of esters and amides from aromatic systems

A new copper-grafted mesoporous poly-melamine-formaldehyde (Cu-mPMF) has been synthesized from melamine and paraformaldehyde in DMSO medium, followed by grafting of Cu(ii) at its surface. Cu-mPMF has been characterized by elemental analysis, powder XRD, HR TEM, FE-SEM, N2 adsorption study, FT-IR, UV-vis DRS, TGA-DTA, EPR spectroscopy, Raman spectroscopy and X-ray photoelectron spectroscopy (XPS). The Cu-grafted mesoporous material showed very good catalytic activity in methyl esterification of benzylic alcohols and amidation of nitriles. Moreover, the catalyst is easily recoverable and can be reused seven times without appreciable loss of catalytic activity in the above reactions. The highly dispersed and strongly bound Cu(ii) sites in the Cu-grafted mesoporous polymer could be responsible for the observed high activities of the Cu-mPMF catalyst. Due to strong binding with the functional groups of the polymer, no evidence of leached copper from the catalyst during the course of reaction emerged, suggesting true heterogeneity in the catalytic process. This journal is