1201-38-3

Basic information

• Product Name: 2',5'-Dimethoxyacetophenone
• Synonyms: Methyl 2,5-dimethoxyphenyl ketone;2,5-Dimethoxy acetonphenone;2',5'-Dimethoxyacetophenone,99%;2',5'-Dimethoxyaceto;1-(2,5-dimethoxyphenyl)-ethanon;Acetophenone, 2',5'-dimethoxy-;AKOS BBS-00004326;1-(2,5-dimethoxyphenyl)-ethanone
• CAS NO: 1201-38-3
• Molecular Formula: C₁₀H₁₂O₃
• Molecular Weight: 180.2
• EINECS: 214-858-0
• Product Categories: C10;Carbonyl Compounds;Ketones;Acetophenone series;Aromatic Acetophenones & Derivatives (substituted)
• Mol File: 1201-38-3.mol
• Article Data: 44

Chemical Properties

• Melting Point: 18-20 °C(lit.)
• Boiling Point: 155-158 °C11 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear yellow to green-yellow/Liquid
• Density: 1.139 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.5441(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform, Methanol (Slightly)
• BRN: 2047423
• CAS DataBase Reference: 2',5'-Dimethoxyacetophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 2',5'-Dimethoxyacetophenone(1201-38-3)
• EPA Substance Registry System: 2',5'-Dimethoxyacetophenone(1201-38-3)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 24/25
• WGK Germany: 3
• TSCA: Yes
• HazardClass: IRRITANT
• Hazardous Substances Data: 1201-38-3(Hazardous Substances Data)

Usage

Description

2',5'-Dimethoxyacetophenone is a clear yellow to green-yellow liquid that serves as a valuable building block in the synthesis of various compounds with potential applications in the pharmaceutical industry.

Uses

Used in Pharmaceutical Industry:
2',5'-Dimethoxyacetophenone is used as a key intermediate for the preparation of pyridine and thieno[2,3-b]pyridine derivatives, which are known as anticancer PIM-1 kinase inhibitors. These inhibitors play a crucial role in the development of targeted cancer therapies, as they help in modulating the activity of specific enzymes involved in cancer cell growth and survival.
Additionally, 2',5'-Dimethoxyacetophenone is utilized in the synthesis of anti-cancer and apoptosis-inducing agents. These agents are designed to trigger programmed cell death (apoptosis) in cancer cells, thereby contributing to the development of novel cancer treatment strategies.

Preparation

Obtained by reaction of dimethyl sulfate with quinacetophenone in the presence of 10% aqueous sodium hydroxide.

Upstream product

• 75-05-8 acetonitrile 
• 150-78-7 1,4-dimethoxybezene 
• 7446-70-0 aluminium trichloride 
• 60-29-7 diethyl ether 
• 75-36-5 acetyl chloride 
• 41038-40-8 1-(2,5-bis(methoxy)phenyl)ethan-1-ol 
• 64-19-7 acetic acid 
• 14568-68-4 1,4-dimethoxy-2-vinylbenzene 
• 75-16-1 methylmagnesium bromide 
• 93-02-7 2,5-dimethoxybenzaldehyde 
• 2785-98-0 2,5-dimethoxybenzoic acid 
• 72229-44-8 2',5'-dimethoxyacetophenone dimethyl acetal 
• 150-76-5 4-methoxy-phenol 
• 127-17-3 2-oxo-propionic acid 

Downstream Products

• 109469-64-9 2-hydroxy-3,2',5'-trimethoxy-trans-chalcone 
• 65547-50-4 1-(2,5-dimethoxy-phenyl)-butane-1,3-dione 
• 110048-16-3 2,3,2',5'-tetramethoxy-trans-chalcone 
• 74605-12-2 2-Amino-4-(2',5'-dimethoxy)phenylthiazole 
• 127034-22-4 (E)-1-(2,5-dimethoxyphenyl)-3-(4-N,N-dimethylaminophenyl)prop-2-en-1-one 
• 81008-14-2 4-(2,5-dimethoxyphenyl)-4-oxo-2-hydroxy-butanoic acid 
• 208937-71-7 [1-(2,5-Dimethoxy-phenyl)-vinyloxy]-diphenyl-silane 
• 221194-99-6 1-(2,5-dimethoxyphenyl)-3-hydroxy-9-phenylnonan-1-one 
• 158531-82-9 4-chloro-2'-hydroxy-5'-methoxychalcone 

Relevant articles and documents

Solid supported Ru(0) nanoparticles: An efficient ligand-free heterogeneous catalyst for aerobic oxidation of benzylic and allylic alcohol to carbonyl

Polymer immobilized stable, spherical ruthenium nanoparticles were prepared, characterized, and acted as a heterogeneous catalyst for the selective benzylic and allylic alcohol oxidation into the corresponding carbonyls using molecular oxygen. The solid supported Ru(0) (SS-Ru) as a heterogeneous catalyst exhibits good reusability and easy separation from the reaction mixture by filtration.

Solid-supported Pd(0): An efficient heterogeneous catalyst for aerobic oxidation of benzyl alcohols into aldehydes and ketones

Solid-supported nano- and microparticles of Pd(0) (SS-Pd) were used as heterogeneous catalysts for aerobic oxidation of benzyl alcohols. Primary and secondary benzyl alcohols gave the corresponding products in good yields. In addition, the catalysts could be reused up to five runs without significant loss of activities.

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Preparation method of 2, 5-dimethoxyphenylacetic acid

The invention belongs to the technical field of drug synthesis, and particularly relates to a preparation method of 2, 5-dimethoxyphenylacetic acid, which comprises the following steps: A. Reacting 1,4-dimethoxybenzene with formaldehyde under the action of hydrogen halide, extracting by the reaction system, merging with organic phases, drying, concentrating under reduced pressure, and purifying the crude product to obtain 2-halon methyl-1, 4-dimethoxybenzene ; and B, under the protection of inert gas, putting the 2-halo methyl-1, 4-dimethoxybenzene obtained in the step A, magnesium or butyl lithium and carbon dioxide into a solvent, and then carrying out extraction and deactivation, reduced pressure distillation, extraction, organic phase combination and reduced pressure concentration toobtain the 2, 5-dimethoxyphenylacetic acid. The yield and the total yield of the 2, 5-dimethoxyphenylacetic acid obtained by the method disclosed by the invention are both higher than those of the 2,5-dimethoxyphenylacetic acid synthesized by a Willgerodt-Kindler method.

Preparation method of 2,5-dimethoxyphenylacetic acid

The invention belongs to the technical field of drug synthesis, and particularly relates to a preparation method of 2,5-dimethoxyphenylacetic acid, wherein the method comprises the following steps: A,reacting 1,4-dimethoxybenzene in a formylation system to obtain 2,5-dimethoxybenzaldehyde; B, reacting the 2,5-dimethoxybenzaldehyde obtained in the step A with a reducing agent, extracting a reaction system, then combining organic phases, drying, concentrating under reduced pressure and distilling a crude product to obtain 2,5-dimethoxybenzyl alcohol; C, reacting the 2,5-dimethoxybenzyl alcoholobtained in the step B with a bromination reagent to obtain 2-bromomethyl-1,4-dimethoxybenzene; and D, reacting the 2-bromomethyl-1,4-dimethoxybenzene obtained in the step C with magnesium or butyl lithium and carbon dioxide in a solvent to obtain the 2,5-dimethoxyphenylacetic acid. The yield and the total yield of the 2,5-dimethoxyphenylacetic acid obtained by the method disclosed by the invention are both higher than those of 2,5-dimethoxyphenylacetic acid synthesized by a Willegerdt-Kindler method.