1,3,5-Trimethoxybenzene

Base Information

• Chemical Name: 1,3,5-Trimethoxybenzene
• CAS No.: 621-23-8
• Molecular Formula: C9H12O3
• Molecular Weight: 168.192
• Hs Code.: 29093090
• European Community (EC) Number: 210-673-4
• NSC Number: 90060
• UNII: 00VJI3VG3D
• DSSTox Substance ID: DTXSID0045963
• Nikkaji Number: J6.831D
• Wikidata: Q27114090
• Metabolomics Workbench ID: 54325
• ChEMBL ID: CHEMBL1605492
• Mol file: 621-23-8.mol

Synonyms:1,3,5-trimethoxybenzene;trimethylphloroglucinol

Chemical Property of 1,3,5-Trimethoxybenzene

Chemical Property:

• Appearance/Colour: white to cream crystalline powder
• Vapor Pressure: 0.0239mmHg at 25°C
• Melting Point: 50-53 °C(lit.)
• Refractive Index: 1,533
• Boiling Point: 257 °C at 760 mmHg
• Flash Point: 85.6 °C
• PSA: 27.69000
• Density: 1.041 g/cm³
• LogP: 1.71240
• Storage Temp.: Store below +30°C.
• Solubility.: methanol: 0.1 g/mL, clear, colorless
• Water Solubility.: insoluble
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 168.078644241
• Heavy Atom Count: 12
• Complexity: 91.2

Purity/Quality:

99% ^*data from raw suppliers

1,3,5-Trimethoxybenzene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn; F
• Hazard Codes: Xn,F
• Statements: 22-20/21/22
• Safety Statements: 24/25-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Ethers, Other
• Canonical SMILES: COC1=CC(=CC(=C1)OC)OC
• General Description: 1,3,5-Trimethoxybenzene is a key starting material in the synthesis of 1,3,7-trihydroxyxanthone, as demonstrated in a study where it undergoes a five-step transformation involving bromination, lithiation, benzoylation, selective deprotection, cyclization, and demethylation. 1,3,5-Trimethoxybenzene serves as a versatile precursor for regioselective coupling reactions, enabling efficient access to natural xanthones such as osajaxanthone and nigrolineaxanthone F with high yields and selectivity. Its utility in multistep synthetic routes highlights its importance in organic and medicinal chemistry.

Technology Process of 1,3,5-Trimethoxybenzene

There total 140 articles about 1,3,5-Trimethoxybenzene 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%

2,4,6-trimethoxybenzoic acid (570-02-5) → 1,2,3-trimethoxybenzene (621-23-8)

Guidance literature:

With palladium(II) trifluoroacetate; trifluoroacetic acid; In dimethyl sulfoxide; N,N-dimethyl-formamide; at 70 ℃; for 24h;

DOI:10.1021/jo400222c

Reference yield: 99.0%

3,5-dihydroxyphenol (108-73-6) + methyl iodide (74-88-4) → 1,2,3-trimethoxybenzene (621-23-8)

Guidance literature:

With potassium carbonate; In acetone; for 3h; Reflux;

DOI:10.1080/00397911.2020.1771597

Reference yield: 98.0%

1,3,5-trisbromobenzene (626-39-1) + sodium methylate (124-41-4) → 1,2,3-trimethoxybenzene (621-23-8)

Guidance literature:

With methanol; Methyl formate; copper(l) chloride; at 115 ℃; for 2h; Autoclave; Green chemistry;

DOI:10.1007/s11164-014-1917-x

upstream raw materials:

diazomethane

3,5-dihydroxyphenol

diethyl ether

methanol

Downstream raw materials:

9-(2',4',6'-trimethoxyphenyl)-9H-xanthene

2,6-dimethoxy-p-quinone

1-(2,4,6-trimethoxyphenyl)dodecan-1-one

2,4,6-trimethoxybenzaldehyde

Refernces

Stereoelectronic effects determine oxacarbenium vs β-sulfonium ion mediated glycosylations

10.1021/ol1027267

The study focuses on the stereoelectronic effects that determine whether glycosylations proceed through oxacarbenium or α-sulfonium ion intermediates. The researchers investigated the influence of protecting groups and the constitution of the C-2 chiral auxiliary on the glycosylation pathway and the resulting anomeric outcome. They found that electron-withdrawing protecting groups, such as acetyl esters, favor the formation of α-sulfonium ions, leading to R-glycosides through an SN2-like displacement. In contrast, electron-donating protecting groups, like benzyl ethers, result in a mixture of anomers due to an equilibrium between sulfonium and oxacarbenium ions. The study also highlighted the importance of the chiral auxiliary's constitution, showing that certain substituents can enhance the stability of the sulfonium ion and promote selective glycosylation. These findings provide guidance for selecting glycosyl donors that can achieve exclusive 1,2-cis stereoselectivity in the synthesis of complex oligosaccharides.

Facile synthesis of 1,3,7-trihydroxyxanthone and its regioselective coupling reactions with prenal: Simple and efficient access to osajaxanthone and nigrolineaxanthone F

10.1021/jo0606655

The research aims to develop a simple and efficient method for synthesizing 1,3,7-trihydroxyxanthone and its subsequent regioselective coupling reactions with prenal to exclusively produce the natural products osajaxanthone and nigrolineaxanthone F. The study describes a five-step synthesis of 1,3,7-trihydroxyxanthone starting from 1,3,5-trimethoxybenzene, involving NBS-induced bromination, lithiation, benzoylation, selective deprotection, intramolecular cyclization, and demethylation, achieving an overall yield of 62%. The regioselective coupling reactions with prenal were conducted under different conditions: at room temperature with calcium hydroxide yielding osajaxanthone (75% yield) and under thermal conditions at 140-150 °C yielding nigrolineaxanthone F (98% yield). The study concludes that this approach offers a straightforward and efficient route to these xanthones, with high yields and selectivity, providing a significant improvement over previous methods. The structures of the compounds were confirmed using analytical and spectral data, including X-ray crystallography.