1450657-28-9

Basic information

• Product Name: 1-(3-Ethoxy-4-Methoxyphenyl)-2-(Methylsulfonyl) ethanone
• Synonyms: 1-(3-Ethoxy-4-Methoxyphenyl)-2-(Methylsulfonyl) ethanone;1-(3-Ethoxy-4-methoxy-phenyl)-2-methanesulfonyl-ethanone
• CAS NO: 1450657-28-9
• Molecular Formula: C₁₂H₁₆O₅S
• Molecular Weight: 272.31744
• EINECS: -0
• Product Categories: ApreMilast;apremilast intermediates
• Mol File: 1450657-28-9.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 1-(3-Ethoxy-4-Methoxyphenyl)-2-(Methylsulfonyl) ethanone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3-Ethoxy-4-Methoxyphenyl)-2-(Methylsulfonyl) ethanone(1450657-28-9)
• EPA Substance Registry System: 1-(3-Ethoxy-4-Methoxyphenyl)-2-(Methylsulfonyl) ethanone(1450657-28-9)

Safety Data

• Hazardous Substances Data: 1450657-28-9(Hazardous Substances Data)

Usage

General Description

1-(3-Ethoxy-4-Methoxyphenyl)-2-(Methylsulfonyl) ethanone, also known as EMSO, is a chemical compound with a molecular formula C12H16O5S. It is a yellow solid with a molecular weight of 272.31 g/mol. EMSO is commonly used as a building block in the synthesis of various pharmaceutical and agrochemical products. It is also utilized as an intermediate in the production of organic compounds and as a reagent in chemical reactions. EMSO has a variety of applications in the chemical and pharmaceutical industries due to its unique structure and properties.

Upstream product

• 253168-94-4 2-(3-ethoxy-4-methoxyphenyl)-1-(methylsulfonyl)eth-2-ylamine 
• 881919-82-0 3-ethoxy-4-methoxyphenylacetylene 
• 20277-69-4 sodium methansulfinate 
• 613-70-7 2-methoxyphenyl acetate 
• 74-96-4 ethyl bromide 
• 645-08-9 Isovanillic acid 
• 6702-50-7 3-hydroxy-4-methoxybenzoate 
• 1131-52-8 3-ethoxy-4-methoxybenzaldehyde 
• 31526-71-3 3-ethoxy-4-methoxy-acetophenone 
• 124-63-0 methanesulfonyl chloride 
• 67-71-0 dimethylsulfone 
• 97966-31-9 3-ethoxy-4-methoxybenzoic acid methyl ester 
• 6100-74-9 3-hydroxy-4-methoxyacetophenone 
• 2386-57-4 methanesulfonic acid sodium salt 

Downstream Products

• 608141-41-9 Apremilast 
• 253168-94-4 2-(3-ethoxy-4-methoxyphenyl)-1-(methylsulfonyl)eth-2-ylamine 
• 635705-72-5 4-amino-2-[(1S)-1-(3-ethoxy 4-methoxyphenyl)-2-methanesulfonylethyl]-2,3-dihydro-1H-isoindole-1,3-dione 
• 608141-44-2 R-Apremilast 
• 1450657-43-8 (S)-4-(1-azido-2-(methylsulfonyl)ethyl)-2-ethoxy-1-methoxybenzene 
• 1450657-24-5 (R)-3-ethoxy-4-methoxy-α-[(methylsulfonyl)methyl]benzyl alcohol 
• 608141-43-1 (S)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethanamine-(S)-2-acetamido-4-methylpentanoate 
• 608141-42-0 (S)-2-[1 (3-ethoxy-4-methoxyphenyl)]-1-methanesulfonyl-2-ethylamine 
• 1450759-47-3 (1S,1'S)-[1-(3-ethoxy-4-methoxyphenyl)-2-methanesulfonyl]ethyl-N-(1'-phenylethyl)amine hydrochloride 

Relevant articles and documents

Directed evolution of an amine transaminase for the synthesis of an Apremilast intermediate via kinetic resolution

Apremilast is an important active pharmaceutical ingredient that relies on a resolution to produce the key chiral amine intermediate. To provide a new catalytic and enzymatic process for Apremilast, we performed the directed evolution of the amine transaminase from Vibrio fluvialis. Six rounds of evolution resulted in the VF-8M-E variant with > 400-fold increase specific activity over the wildtype enzyme. A homology model of VF-8M-E was built and a molecular docking study was performed to explain the increase in activity. The purified VF-8M-E was successfully applied to produce the key chiral amine intermediate in enantiopure form and 49% conversion via a kinetic resolution, representing a new enzymatic access towards Apremilast.

Synthetic method of apremilast intermediate

The invention discloses a synthetic method of an apremilast intermediate. The method comprises the following steps of by taking 2-methoxyphenyl acetate and 2-(methylsulfonyl) acetyl chloride as starting materials, carrying out acylation reaction and hydrolysis under the catalysis of aluminum trichloride to obtain 1-(3-hydroxy-4-methoxyphenyl)-2-(methylsulfonyl) ethyl ketone, carrying out alkylation reaction with bromoethane, and then forming imine with ammonium acetate, and reducing to form the 1-(3-ethoxy-4-methoxy phenyl)-2-(methylsulfonyl) ethylamine. The method is simple to operate, avoids the use of n-butyllithium, palladium on carbon and mesylate, avoids the problems of high risk, high cost and the like, and is suitable for industrial production.

For treating psoriasis sexual arthritis disease apps is special synthetic method (by machine translation)

The invention discloses a method for treating psoriasis sexual arthritis disease apps is special synthetic method, the method to 3 - ethoxy - 4 - methoxybenzaldehyde as the starting material, by with the dimethyl sulfone, n-butyl reaction, to obtain 3 - ethoxy - 4 - methoxy - α - [(methylsulfonyl) methyl] - benzene methanol, through the oxidation reaction to obtain 1 - (3 - ethoxy - 4 - methoxyphenyl) - 2 - methyl-sulfonyl - ethanone, through the reduction reaction to obtain the R - 3 - ethoxy - 4 - methoxy - α - [(methylsulfonyl) methyl] - benzene methanol, finally with 3 - acetamide group ortho-phthalic acid imide by Mitsunobu reaction, to obtain the target product apps is special. The invention has mild reaction condition, the process is simple, the yield is good, easy industrialization and the like. (by machine translation)