2040-04-2

Basic information

• Product Name: 2',6'-Dimethoxyacetophenone
• Synonyms: 2',6'-DIMETHOXYACETOPHENONE;2,6-DIMETHOXYACETOPHENONE;1-(2,6-DIMETHOXYPHENYL)ETHANONE;1-(2,6-dimethoxyphenyl)-ethanon;2’,6’-dimethoxy-acetophenon;Acetophenone, 2',6'-dimethoxy-;Ethanone, 1-(2,6-dimethoxyphenyl)-;USAF K-2801
• CAS NO: 2040-04-2
• Molecular Formula: C₁₀H₁₂O₃
• Molecular Weight: 180.2
• EINECS: 218-034-1
• Product Categories: Aromatic Acetophenones & Derivatives (substituted);C10;Carbonyl Compounds;Ketones;Building Blocks;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 2040-04-2.mol
• Article Data: 21

Chemical Properties

• Melting Point: 68-70 °C(lit.)
• Boiling Point: 135-136 °C2 mm Hg(lit.)
• Flash Point: 135-136°C/2mm
• Appearance: White to beige/Crystalline Powder
• Density: 1.1272 (rough estimate)
• Vapor Pressure: 0.000488mmHg at 25°C
• Refractive Index: 1.5430 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• BRN: 2048976
• CAS DataBase Reference: 2',6'-Dimethoxyacetophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 2',6'-Dimethoxyacetophenone(2040-04-2)
• EPA Substance Registry System: 2',6'-Dimethoxyacetophenone(2040-04-2)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• RTECS: AM8400000
• HazardClass: IRRITANT
• Hazardous Substances Data: 2040-04-2(Hazardous Substances Data)

Usage

Uses

2′,6′-Dimethoxyacetophenone was used in preparation of 4-fluororesorcinol.

Synthesis Reference(s)

Tetrahedron, 49, p. 10843, 1993 DOI: 10.1016/S0040-4020(01)80238-6

General Description

2,6-Dihydroxyacetophenone, its mono- and di-methyl ethers are inhibitors of hepatic mixed function oxidases. Metabolism of 2′,6′-dimethoxyacetophenone was studied.

InChI:InChI=1/C10H12O3/c1-7(11)10-8(12-2)5-4-6-9(10)13-3/h4-6H,1-3H3

Upstream product

• 699-83-2 2,6-dihydroxylacetophenone 
• 77-78-1 dimethyl sulfate 
• 141-78-6 ethyl acetate 
• 151-10-0 1,3-Dimethoxybenzene 
• 75-36-5 acetyl chloride 
• 108-24-7 acetic anhydride 
• 99501-03-8 (±)-1-(2,6-dimethoxyphenyl)ethanol 
• 148230-18-6 methyl α-(2,6-dimethoxyphenyl)vinyl ether 
• 1466-76-8 2-6-dimethoxybenzoic acid 
• 1242030-69-8 (2-(2,6-dimethoxyphenyl)ethynyl)trimethylsilane 
• 16932-44-8 2-iodo-1,3-dimethoxybenzene 
• 126829-31-0 1-ethynyl-2,6-dimethoxybenzene 
• 703-23-1 2'-hydroxy-6'-methoxyacetophenone 
• 616-38-6 carbonic acid dimethyl ester 

Downstream Products

• 99501-03-8 (±)-1-(2,6-dimethoxyphenyl)ethanol 
• 121883-87-2 2-(1,2-Dimethyl-propenyl)-1,3-dimethoxy-benzene 
• 16929-70-7 1,3-dimethoxy-2-(1-hydroxy-1-methylethyl)benzene 
• 82210-48-8 3-hydroxy-3-(2,6-dimethoxyphenyl)-but-1-ene 
• 18610-90-7 1,3-dimethoxy-2-ethylbenzene 
• 132338-43-3 α-(2,6-dimethoxyphenyl)vinyl chloride 
• 117902-11-1 2,6-dimethoxy-3-fluoroacetophenone 
• 153142-69-9 2,6-dimethoxyacetophenone enol 
• 117379-77-8 (E)-4-(2,6-dimethoxyphenyl)-4-oxo-2-butenoic acid 
• 699-83-2 2,6-dihydroxylacetophenone 
• 31709-82-7 (2,6-dimethoxy-phenyl)-glyoxylic acid 
• 101689-20-7 2,6-Dimethoxyphenylglyoxal 
• 151-10-0 1,3-Dimethoxybenzene 
• 103204-08-6 1-(3-iodo-2,6-dimethoxy-phenyl)-ethanone 

Relevant articles and documents

Theoretical and experimental investigation of palladium(II)-catalyzed decarboxylative addition of arenecarboxylic acid to nitrile

The reaction mechanism of palladium(II)-catalyzed decarboxylative addition of 2,6-dimethoxybenzoic acid to acetonitrile was investigated by means of density functional theory (DFT) calculations. Calculations of the free energy profile for decarboxylation and carbopalladation indicated carbopalladation as the rate-determining step of the reaction. Investigation of the free energy profile for a series of experimentally evaluated nitrogen-based bidentate palladium ligands revealed that higher energy is required for decarboxylation and carbopalladation employing the experimentally least efficient ligand. The DFT investigation also showed that the relative free energies of the transition states were lowered in polar solvent, and preparative experiments confirmed that a nonoptimal ligand could be greatly improved by addition of water to the reaction system.

Ni-Catalyzed β-Alkylation of Cyclopropanol-Derived Homoenolates

Metal homoenolates are valuable synthetic intermediates which provide access to β-functionalized ketones. In this report, we disclose a Ni-catalyzed β-alkylation reaction of cyclopropanol-derived homoenolates using redox-active N-hydroxyphthalimide (NHPI) esters as the alkylating reagents. The reaction is compatible with 1°, 2°, and 3° NHPI esters. Mechanistic studies imply radical activation of the NHPI ester and 2e β-carbon elimination occurring on the cyclopropanol.

Hexafluoro-2-propanol-Promoted Intermolecular Friedel-Crafts Acylation Reaction

The intermolecular Friedel-Crafts acylation was carried out in hexafluoro-2-propanol to yield aryl and heteroaryl ketones at room temperature without any additional reagents.