4783-90-8

Usage

Uses

Used in Pharmaceutical Industry:
2-chloro-2-4-dimethoxyacetophenone is utilized as an intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the development of anti-inflammatory, antibacterial, and antifungal medicines. Its chemical structure allows for the creation of compounds that can effectively target and treat a range of conditions.
Used in Agrochemical Industry:
In the agrochemical sector, 2-chloro-2-4-dimethoxyacetophenone is employed as a crucial component in the production of agrochemicals, highlighting its versatility and importance in different chemical domains.
Used in Dye Industry:
2-chloro-2-4-dimethoxyacetophenone is used as an intermediate for the synthesis of dyes, capitalizing on its chemical properties to produce a spectrum of colorants for various applications.
Used in Perfumery:
2-chloro-2-4-dimethoxyacetophenone is also used as an ingredient in the preparation of perfumes, where its aromatic characteristics contribute to the creation of diverse fragrances.
Used in Flavoring Industry:
2-chloro-2-4-dimethoxyacetophenone is utilized in the development of flavoring agents, enhancing the taste profiles of food products and beverages.
Used in Enzyme Inhibition Research:
As a potent enzyme inhibitor, 2-chloro-2-4-dimethoxyacetophenone is applied in research and development for new therapeutics, potentially leading to breakthroughs in the treatment of various diseases and conditions.

InChI:InChI=1/C10H11ClO3/c1-13-7-3-4-8(9(12)6-11)10(5-7)14-2/h3-5H,6H2,1-2H3

Upstream product

• 60965-26-6 2-Bromo-2',4'-dimethoxyacetophenone 
• 829-20-9 2',4'-dimethoxyacetophenone 
• 192071-32-2 2-diazo-1-(3,4-dimethoxyphenyl)ethanone 
• 68-12-2 N,N-dimethyl-formamide 
• 107-14-2 chloroacetonitrile 
• 151-10-0 1,3-Dimethoxybenzene 

Downstream Products

• 93258-91-4 4-(2,4-dimethoxy-phenyl)-3H-thiazol-2-one 
• 65782-69-6 2-(benzo[d]thiazol-2-ylthio)-1-(2,4-dimethoxyphenyl)ethan-1-one 
• 448908-41-6 4-(2,4-dimethoxy-phenyl)-2-methyl-thiazole 
• 23111-45-7 4-(2,4-dimethoxyphenyl)thiazol-2-amine 
• 24361-17-9 (Z)-4-Chloro-2-cyano-3-(2,4-dimethoxy-phenyl)-but-2-enoic acid ethyl ester 
• 119730-15-3 2-(2,4-dimethoxybenzoylmethylthio)-6-methylpyrimidin-4(1H)-one 
• 7051-13-0 1-chloro-2,4-dimethoxybenzene 
• 6496-89-5 2,4-dimethoxyphenylacetic acid 
• 829-20-9 2',4'-dimethoxyacetophenone 
• 119730-56-2 2-(2,4-dimethoxybenzoylmethylene)-6-methyl-2,3-dihydropyrimidin-4(1H)-one 
• 882528-44-1 1-(2,4-dimethoxy-phenyl)-2-(4-fluoro-phenoxy)-ethanone 
• 23111-50-4 N-[4-(2,4-dimethoxy-phenyl)-thiazol-2-yl]-propionamide 
• 23111-16-2 N-[4-(2,4-dimethoxy-phenyl)-thiazol-2-yl]-3,4,5-trimethoxy-benzamide 
• 23111-21-9 2-(4-chloro-phenoxy)-N-[4-(2,4-dimethoxy-phenyl)-thiazol-2-yl]-acetamide 

Relevant academic research and scientific papers

Opening or closing the lock? when reactivity is the key to biological activity

Thiol-mediated processes play a key role to induce or inhibit inflammation proteins. Tailoring the reactivity of electrophiles can enhance the selectivity to address only certain surface cysteines. Fourteen 2',3,4,4'- tetramethoxychalcones with different α-X substituents (X=H, F, Cl, Br, I, CN, Me, p-NO2-C6H4, Ph, p-OMe-C 6H4, NO2, CF3, COOEt, COOH) were synthesized, containing the potentially electrophilic α,β-unsaturated carbonyl unit. The assessment of their reactivity as electrophiles in thia-Michael additions with cysteamine shows a change in the reactivity of more than six orders of magnitude. Moreover, a clear correlation between their reactivity and an influence on the inflammation proteins heme oxygenase-1 (HO-1) and the inducible NO synthase (iNOS) is demonstrated. As the biologically most active compound, the α-CF3-chalcone is shown to inhibit the NO production in RAW264.7 mouse macrophages in the nanomolar range. More than a million by only one substituent: The direct manipulation of the chemical reactivity of electrophilic agents could be proven for chalcones by simply exchanging the α-hydrogen atom of the α,β-unsaturated carbonyl unit with different substituents (X), leading to a change in reactivity of more than six orders of magnitude for thia-Michael additions with cysteamine, which correlates very well with two electrophile-sensitive biological readouts (see scheme).

Diazoaldehyde Chemistry: Part 4 - Vilsmeier-Haack Formylation of Diazo Compounds: A Re-investigation

Diazomethyl ketones (2-diazoethanones) were reacted with the Vilsmeier reagent ((chloromethylidene)dimethylammonium chloride) to yield α-diazo-β-oxoaldehydes and chloromethyl ketones. 2′,4′-Dimethoxy-α-diazoacetophenone gave 2-chloro-1-(2,4-dimethoxyphenyl)-3-(dimethylamino)prop-2-en-1-one (5) in addition to the expected products. Phenyldiazomethanes gave the corresponding benzyl chlorides but not the (phenyl)diazoacetaldehydes even at temperatures as low as -60°. The diazo-transfer reactions of phenylacetaldehydes and 2-azido-1-ethylpyridin-1-ium tetrafluoroborate also did not yield the expected(phenyl)diazoacetaldehydes.

The Chemistry of Nitrilium Salts. Part 1. Acylation of Phenols and Phenol Ethers with Nitriles and Trifluoromethanesulphonic Acid

Aliphatic nitriles, RCN (R = Me, n-Pr, CH2Cl, and CCl3), in the presence of trifluoromethanesulphonic acid have been found to react with a number of mono-, di-, and tri-substituted phenols and phenol ethers at room temperature to give ketones after hydrolysis of the reaction mixture.Moderate to good yields of acylation products are obtained in the majority of these reactions.The yield with malononitrile and succinonitrile, which are only slightly soluble in the reaction medium, are generally poor, and reaction involves only one of the available nitrile groups.Attempts to use diethyl ether and dichloromethane as solvents for some of these reactions were unsuccessful, but limited success was achieved with nitromethane.