3,4-Dimethoxyphenylacetone

Base Information

• Chemical Name: 3,4-Dimethoxyphenylacetone
• CAS No.: 776-99-8
• Molecular Formula: C11H14O3
• Molecular Weight: 194.23
• Hs Code.: 2914509090
• European Community (EC) Number: 212-285-0
• NSC Number: 16700
• UNII: DM28QN9QDY
• DSSTox Substance ID: DTXSID00228267
• Nikkaji Number: J41.172H
• Wikidata: Q72468229
• ChEMBL ID: CHEMBL1163509
• Mol file: 776-99-8.mol

Synonyms:3,4-dimethoxyphenylacetone

Chemical Property of 3,4-Dimethoxyphenylacetone

Chemical Property:

• Appearance/Colour: colorless transparent liquid
• Vapor Pressure: 0.00349mmHg at 25°C
• Refractive Index: n20/D 1.5358(lit.)
• Boiling Point: 295.2 °C at 760 mmHg
• Flash Point: 123.2 °C
• PSA: 35.53000
• Density: 1.047 g/cm³
• LogP: 1.83530
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility.: Insoluble in water.
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 194.094294304
• Heavy Atom Count: 14
• Complexity: 191

Purity/Quality:

99.0% min ^*data from raw suppliers

3,4-Dimethoxyphenylacetone >97.0%(GC) ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)CC1=CC(=C(C=C1)OC)OC
• Uses: 3,4-Dimethoxyphenylacetone was used as starting material in the synthesis of α-methyl-dopa, an important nonproteogenic α-amino acid for pharmaceutical applications. 3,4-Dimethoxyphenylacetone undergoes asymmetric amination catalyzed by Brevibacterium linens IFO 12141 strain to yield corresponding optically active amine

Technology Process of 3,4-Dimethoxyphenylacetone

There total 62 articles about 3,4-Dimethoxyphenylacetone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

methylmagnesium bromide (75-16-1) + 3,4-dimethoxyphenylacetic acid N,O-dimethylhydroxyamide (155955-78-5) → 3,4-dimethoxyphenylacetone (776-99-8)

Guidance literature:

In tetrahydrofuran; at 0 ℃;

DOI:10.1021/ol0067641

Reference yield: 91.0%

bis(acetonitrile)palladium(II) dichloride + 1,2-dimethoxy-4-(2-propenyl)benzene (93-15-2) → 3,4-dimethoxyphenylacetone (776-99-8) + 1-(3,4-dimethoxyphenyl)-2,2-dimethoxypropane

Guidance literature:

Reference yield: 88.0%

4-Bromoveratrole (2859-78-1) + acetone (67-64-1) → 3,4-dimethoxyphenylacetone (776-99-8)

Guidance literature:

With bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; N-[2-(di(1-adamantyl)phosphino)phenyl]morpholine; caesium carbonate; at 90 ℃; for 16h; Inert atmosphere; sealed vial;

DOI:10.1021/ja200009c

upstream raw materials:

diazomethane

1-(3,4-dihydroxyphenyl)-2-propanone

(3,4-Dimethoxyphenyl)acetic acid

1-(3,4-dimethoxyphenyl)-2-nitropropene

Downstream raw materials:

1-(3,4-dimethoxyphenyl)-N-methylpropan-2-amine

α,β-dimethyl-γ-(3,4-dimethoxyphenyl) butyrolactone

5-(3,4-dimethoxy-benzyl)-5-methyl-imidazolidine-2,4-dione

(±)-3-(3,4-dimethoxyphenyl)-2-amino-2-methylpropanenitrile

Refernces

New, lithiation-based synthesis of tofisopam, A 2,3-benzodiazepine type anxiolytic drug

10.3987/COM-13-S(S)15

The study presents a new, environmentally friendly synthesis method for tofisopam, a 2,3-benzodiazepine type anxiolytic drug, which avoids the use of toxic chromium(VI) oxide reagents traditionally used in its production. The research focuses on replacing the hazardous chromium-based oxidation step with a lithiation-based approach to produce the key intermediate, a keto-ketal compound. The chemicals used in the study include (3,4-dimethoxyphenyl)acetone, bromine, lithium compounds (hexyllithium), 3,4-dimethoxybenzoyl chloride, and hydrazine, among others. These chemicals serve various purposes in the synthesis process, such as starting materials, reagents for protection and deprotection of functional groups, and agents for the lithiation and cyclization steps, ultimately leading to the formation of tofisopam without the environmental and health risks associated with chromium salts.