4'-Methoxyacetophenone

Base Information

• Chemical Name: 4'-Methoxyacetophenone
• CAS No.: 100-06-1
• Molecular Formula: C9H10O2
• Molecular Weight: 150.177
• Hs Code.: 29145000
• European Community (EC) Number: 202-815-9
• NSC Number: 209523,5601
• UNII: 0IRH2BR587
• DSSTox Substance ID: DTXSID2044347
• Nikkaji Number: J5.163B
• Wikipedia: Acetanisole
• Wikidata: Q229995
• RXCUI: 2612428
• Metabolomics Workbench ID: 45615
• ChEMBL ID: CHEMBL401912
• Mol file: 100-06-1.mol

Synonyms:4-acetylanisole;4-methoxyacetophenone

Chemical Property of 4'-Methoxyacetophenone

Chemical Property:

• Appearance/Colour: White crystals or crystalline powder
• Vapor Pressure: 0.42Pa at 20℃
• Melting Point: 36-38 °C(lit.)
• Refractive Index: 1.5470 (estimate)
• Boiling Point: 256.4 °C at 760 mmHg
• Flash Point: 113.2 °C
• PSA: 26.30000
• Density: 1.035 g/cm³
• LogP: 1.89780
• Storage Temp.: Store below +30°C.
• Sensitive.: Light Sensitive
• Solubility.: H2O: soluble2.474g/L at 20°C
• Water Solubility.: insoluble
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 150.068079557
• Heavy Atom Count: 11
• Complexity: 135

Purity/Quality:

99% ^*data from raw suppliers

4'-Methoxyacetophenone 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-38-36/38-20/21/22
• Safety Statements: 37-37/39-26-36

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Other Aromatic Compounds
• Canonical SMILES: CC(=O)C1=CC=C(C=C1)OC
• Description: Yellowish-white crystals with an odor similar to that of p-methylacetopheneone, suggestive of hawthorn and floral note of heliotrope, possessing a bitter and unpleasant taste. Useful in vanilla, nut, tobacco and butter flavors.
• Uses: 4'-Methoxyacetophenone is used as a component of perfumes and as chemical intermediate in the manufacture of pharmaceuticals, resins, flavouring agents. And also used to study ruthenium catalyzed step growth copolymerization of 4?-methoxyacetophenone with α,ω-dienes to yield copolymers. 4'-Methoxyacetophenone is a solid, pale yellow flavoring agent with a hawthornlike odor. It is soluble in most fixed oils and propylene glycol, and it is insoluble in glycerin and mineral oil. It is obtained by chemical synthesis. This flavoring substance or its adjuvant may be safely used in food in the minimum quantity required to produce its intended flavor. It can be used alone or in combination with other flavoring substances or adjuvants. It is also termed p-methoxyacetophenone. Perfumery (for floral odors), flavoring.

Technology Process of 4'-Methoxyacetophenone

There total 670 articles about 4'-Methoxyacetophenone 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: 99.0%

methoxybenzene (100-66-3) + acetyl chloride (75-36-5) → 1-(4-methoxyphenyl)ethanone (100-06-1)

Guidance literature:

With aluminium trichloride; 1-ethyl-3-methyl-1H-imidazol-3-ium chloride; at -10 ℃; for 0.25h;

Reference yield: 97.0%

4-Methoxystyrene (637-69-4,24936-44-5) → rac-1-(4-methoxyphenyl)-ethanol (3319-15-1) + 1-(4-methoxyphenyl)ethanone (100-06-1)

Guidance literature:

With 2.9-dimethyl-1,10-phenanthroline; phenylsilane; iron(II) chloride; In ethanol; at 20 ℃; for 4.5h; Reagent/catalyst;

DOI:10.1002/anie.202103222

Reference yield: 96.0%

dimethyl sulfate (77-78-1) + 4-Hydroxyacetophenone (99-93-4) → 1-(4-methoxyphenyl)ethanone (100-06-1)

Guidance literature:

With poly(ethylene glycol) 400; sodium carbonate; at 110 ℃; for 10h;

DOI:10.1080/00397910008087221

upstream raw materials:

4-Methoxystyrene

1-methyl-4-nitrosobenzene

4-(4-methoxy-phenyl)-pent-3-en-2-one

3-(4-methoxy-phenyl)-5-oxo-hex-2-enoic acid

Downstream raw materials:

N-<2-(4-Methoxyphenyl)-1-thioxoethyl>piperidine

1-(4-methoxy-phenyl)-3-(4-propyl-piperidino)-propan-1-one

1-(4-methoxyphenyl)-1-(pyridin-2-yl)ethanol

1-(2-(4-methoxyphenyl)-2-oxoethyl)pyridin-1-ium iodide

Refernces

Lewis Acid-Catalyzed Synthesis of Benzofurans and 4,5,6,7-Tetrahydrobenzofurans from Acrolein Dimer and 1,3-Dicarbonyl Compounds

10.1021/acs.joc.9b00270

The study presents a novel Lewis acid-catalyzed approach for the synthesis of benzofurans and 4,5,6,7-tetrahydrobenzofurans from acrolein dimer and 1,3-dicarbonyl compounds. The method employs N-bromosuccinimide (NBS) as an oxidizing agent and utilizes a combination of Lewis acid catalysts to achieve high yields of 2,3-disubstituted benzofurans. The researchers successfully synthesized two commercial drug molecules, benzbromarone and amiodarone, using this method. The study also explores the substrate scope and optimizes the reaction conditions. Additionally, the authors propose a mechanism involving NBS-assisted auto-tandem catalysis and provide evidence by isolating an intermediate that can be further converted to tetrahydrobenzofurans. This work offers an efficient and practical route to synthesize benzofuran derivatives with potential applications in pharmaceutical chemistry.