2,4,6-Trimethoxytoluene

Base Information

• Chemical Name: 2,4,6-Trimethoxytoluene
• CAS No.: 14107-97-2
• Molecular Formula: C10H14 O3
• Molecular Weight: 182.219
• Hs Code.: 2909309090
• European Community (EC) Number: 237-962-8
• DSSTox Substance ID: DTXSID7065706
• Nikkaji Number: J216.868E
• Wikidata: Q81992338
• Mol file: 14107-97-2.mol

Synonyms:2,4,6-Trimethoxytoluene;14107-97-2;1,3,5-Trimethoxy-2-methylbenzene;Benzene, 1,3,5-trimethoxy-2-methyl-;EINECS 237-962-8;SCHEMBL862161;Toluene, 2,4,6-trimethoxy-;DTXSID7065706;1,3,5-trimethoxy-2-methyl-benzene;MFCD00008375;1,3,5-Trimethoxy-2-methylbenzene #;AS-62446;CS-0358017;FT-0609889;1,3,5-Trimethoxy-2-methylbenzene AldrichCPR;1,3,5-Trimethoxy-2-methylbenzene, AldrichCPR;A807725

Chemical Property of 2,4,6-Trimethoxytoluene

Chemical Property:

• Vapor Pressure: 0.0032mmHg at 25°C
• Melting Point: 27-28°C
• Refractive Index: 1.5310
• Boiling Point: 100-105°C 1mm
• Flash Point: 87.8°C
• PSA: 27.69000
• Density: 1.025g/cm³
• LogP: 2.02080
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Sparingly), Methanol (Sparingly)
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 182.094294304
• Heavy Atom Count: 13
• Complexity: 135

Purity/Quality:

97% ^*data from raw suppliers

1,3,5-Trimethoxy-2-methylbenzene ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C=C(C=C1OC)OC)OC
• General Description: 2,4,6-Trimethoxytoluene is a key intermediate in the synthesis of natural products such as aurentiacin and dihydroaurentiacin. It reacts with acids like cinnamic acid and 2-phenylpropionic acid in the presence of boron trifluoride to form boron heterocycles, which are subsequently hydrolyzed to yield the target compounds. 2,4,6-TRIMETHOXYTOLUENE plays a crucial role in selective demethylation and acylation processes, enabling efficient and high-yield synthetic routes for these natural products.

Technology Process of 2,4,6-Trimethoxytoluene

There total 12 articles about 2,4,6-Trimethoxytoluene 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-trimethoxybenzaldehyde (830-79-5) → 2,4,6-trimethoxytoluene (14107-97-2)

Guidance literature:

With sodium cyanoborohydride; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1016/j.tetlet.2016.03.049

Reference yield: 98.0%

2,4,6-trimethoxybenzyl alcohol (61040-78-6) → 2,4,6-trimethoxytoluene (14107-97-2)

Guidance literature:

With triethylsilane; trifluoroacetic acid; In dichloromethane; at -78 - 20 ℃;

DOI:10.1021/jm060692n

Reference yield: 92.0%

1,2,3-trimethoxybenzene (621-23-8) + methyl iodide (74-88-4) → 2,4,6-trimethoxytoluene (14107-97-2)

Guidance literature:

1,2,3-trimethoxybenzene; With n-butyllithium; In tetrahydrofuran; pentane; at 40 ℃; for 24h;

methyl iodide; In tetrahydrofuran; pentane; at -78 - 20 ℃; for 1h;

DOI:10.1021/ol802183p

upstream raw materials:

2,4,6-trimethoxybenzaldehyde

methyl 2,4,6-trimethoxy-3-methylbenzoate

2-hydroxy-4,6-dimethoxytoluene

sodium methylate

Downstream raw materials:

2,2-Difluor-5,7-dimethoxy-8-methyl-4-(2-phenylethyl)-1-oxa-3-oxonia-2-boratanaphthalin

2,6-dimethoxy-3-methyl-1,4-benzoquinone

2,4,6-trimethoxy-3-methylphenol

2,2-Difluor-5,7-dimethoxy-8-methyl-4-(2-phenylvinyl)-1-oxa-3-oxonia-2-boratanaphthalin

Refernces

Trimethoxyphenyl compounds. IX. Boron heterocycles in preparative natural products chemistry: A simple synthesis of aurentiacin

10.1002/jlac.198219820810

The research focuses on the synthesis of aurentiacin and related compounds using boron heterocycles. Key chemicals involved include 2,4,6-trimethoxytoluene, which reacts with various acids such as cinnamic acid and 2-phenylpropionic acid in the presence of boron trifluoride to form boron heterocycles. These heterocycles are then hydrolyzed to yield aurentiacin (3b) and dihydroaurentiacin (3c). The study also explores the selective demethylation and acylation processes, highlighting the formation of intermediate compounds and their properties. The research provides a simple and efficient synthetic route for these natural products, with high yields and purity, contributing to the field of preparative natural products chemistry.