3,5-Dimethoxyphenol

Base Information

• Chemical Name: 3,5-Dimethoxyphenol
• CAS No.: 500-99-2
• Molecular Formula: C8H10O3
• Molecular Weight: 154.166
• Hs Code.: 29095090
• European Community (EC) Number: 207-917-7
• NSC Number: 70955
• UNII: 23UXW8136A
• DSSTox Substance ID: DTXSID7075426
• Nikkaji Number: J107.380J
• Wikidata: Q27160623
• ChEMBL ID: CHEMBL462989
• Mol file: 500-99-2.mol

Synonyms:1,3-dimethoxy-5-hydroxybenzene;3,5-dimethoxyphenol;phloroglucindimethylether;phloroglucinol dimethyl ether

Chemical Property of 3,5-Dimethoxyphenol

Chemical Property:

• Appearance/Colour: slightly pink to yellow crystalline powder
• Vapor Pressure: 0.000944mmHg at 25°C
• Melting Point: 40-43 °C(lit.)
• Refractive Index: 1.522
• Boiling Point: 294.1 °C at 760 mmHg
• PKA: pK1:9.345 (25°C)
• Flash Point: 78.3 °C
• PSA: 38.69000
• Density: 1.134 g/cm³
• LogP: 1.40940
• Storage Temp.: Store in dark!
• Sensitive.: Air & Light Sensitive
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• Water Solubility.: Soluble in methanol, ethanol, benzene, water (slightly), and chloroform.
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 154.062994177
• Heavy Atom Count: 11
• Complexity: 104

Purity/Quality:

98%min, ^*data from raw suppliers

3,5-Dimethoxyphenol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=CC(=C1)O)OC
• Uses: 3,5-Dimethoxyphenol is a phenol derivative as antinitrosating agent. 3,5-dimethoxyphenol is a marker for poisoning from Taxus baccata.

Technology Process of 3,5-Dimethoxyphenol

There total 70 articles about 3,5-Dimethoxyphenol 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: 100.0%

2-(3,5-dimethoxyphenoxy)-1-(3,4-dimethoxyphenyl)ethan-1-ol → 3,5-dimethoxyphenol (500-99-2) + 1-(3,4-dimethoxyphenyl)ethanone (1131-62-0)

Guidance literature:

With C₆₀H₃₆N₂; sodium salt of dibutyl phosphate; Methyl thioglycolate; In dimethyl sulfoxide; at 25 ℃; for 24h; Irradiation; Sealed tube;

DOI:10.1039/c9cc06904f

Reference yield: 99.0%

1,2,3-trimethoxybenzene (621-23-8) → 3,5-dimethoxyphenol (500-99-2)

Guidance literature:

With orcinol; Acetobacterium dehalogenans veratrol-O-demethylase; Desulfitobacterium hafniense methyltransferase dhaf4611; In aq. buffer; at 25 ℃; for 24h; pH=6.5; regioselective reaction; Inert atmosphere; Enzymatic reaction;

DOI:10.1021/acscatal.0c02790

Reference yield: 99.0%

1-iodo-3,5-dimethoxybenzene (25245-27-6) → 3,5-dimethoxyphenol (500-99-2)

Guidance literature:

With copper acetylacetonate; N¹-(4-hydroxy-2,6-dimethylphenyl)-N²-(4-hydroxy-3,5-dimethylphenyl)oxalamide; potassium hydroxide; In water; dimethyl sulfoxide; at 60 ℃; for 24h; Schlenk technique; Inert atmosphere;

DOI:10.1021/jacs.6b08114

upstream raw materials:

methanol

3,5-dihydroxyphenol

1,2,3-trimethoxybenzene

2,4,6,3',4',5'-hexamethoxydiphenyl ether

Downstream raw materials:

2-(3,5-dimethoxyphenoxy)-2-methylpropanoic acid

3,5-dimethoxy-2-prenylphenol

2-hydroxy-4,6-dimethoxybenzaldehyde

2-(3,5-dimethoxy-phenoxy)-propionic acid ethyl ester

Refernces

A Formal Synthesis of Aflatoxin B2

10.1039/c39880000721

This research aims to develop a synthetic route for Aflatoxin B2, a highly toxic and carcinogenic metabolite produced by various Aspergillus species. The study focuses on synthesizing a ring A differentiated tetrahydrofurobenzofuran intermediate, which can be converted into Aflatoxin B2. Key chemicals used in the research include 3,5-dimethoxy phenol, ortho-iodophenol, lead tetra-acetate (LTA), di-isobutylaluminum hydride (DIBAL-H), and t-butyl mercaptide. The researchers successfully synthesized the intermediate compound through a series of reactions, including iodination, reduction, and cyclization, achieving an overall yield of approximately 4%. The study concludes that the synthesized intermediate can be further converted into Aflatoxin B2, demonstrating a feasible synthetic pathway. The research also highlights the challenges in differentiating the oxygen substituents on ring A and presents a method to selectively demethylate the intermediate using t-butyl mercaptide, achieving improved selectivity and yield. This work represents a significant advancement in the synthesis of aflatoxins and lays the foundation for further studies on their structure and toxicity.