5438-54-0

Basic information

• Product Name: 2,6-Dimethoxy-1-(allyloxy)benzene
• Synonyms: (2,6-Dimethoxyphenyl)allyl ether;1,3-Dimethoxy-2-(2-propenyloxy)benzene;1,3-Dimethoxy-2-allyloxybenzene;2,6-Dimethoxy-1-(allyloxy)benzene;Allyl(2,6-dimethoxyphenyl) ether;1,3-dimethoxy-2-prop-2-enoxybenzene;1,3-dimethoxy-2-prop-2-enoxy-benzene;2-allyloxy-1,3-dimethoxy-benzene
• CAS NO: 5438-54-0
• Molecular Formula: C₁₁H₁₄O₃
• Molecular Weight: 194.23
• Mol File: 5438-54-0.mol
• Article Data: 21

Chemical Properties

• Boiling Point: 262°C at 760 mmHg
• Flash Point: 86.2°C
• Appearance: /
• Density: 1.024g/cm³
• Vapor Pressure: 0.0182mmHg at 25°C
• Refractive Index: 1.495
• CAS DataBase Reference: 2,6-Dimethoxy-1-(allyloxy)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-Dimethoxy-1-(allyloxy)benzene(5438-54-0)
• EPA Substance Registry System: 2,6-Dimethoxy-1-(allyloxy)benzene(5438-54-0)

Safety Data

• Hazardous Substances Data: 5438-54-0(Hazardous Substances Data)

Usage

General Description

2,6-Dimethoxy-1-(allyloxy)benzene, also known as eugenol, is a naturally occurring chemical compound found in various plants such as cloves, nutmeg, and cinnamon. It is a pale yellow, oily liquid with a spicy and clove-like odor. Eugenol is commonly used as a flavoring agent in food and beverages due to its pleasant aroma and taste. Additionally, it is used in the production of perfumes, essential oils, and cosmetic products. It also has antimicrobial properties and is used in dental products such as mouthwashes and toothpastes. Furthermore, eugenol has been studied for its potential medicinal properties and has shown promise as an anti-inflammatory and analgesic agent.

InChI:InChI=1/C11H14O3/c1-4-8-14-11-9(12-2)6-5-7-10(11)13-3/h4-7H,1,8H2,2-3H3

Upstream product

• 91-10-1 1,3-dimethoxy-2-hydroxy-benzene 
• 107-05-1 3-chloroprop-1-ene 
• 35466-83-2 allyl methyl carbonate 
• 634-36-6 1,2,3-trimethoxybenzene 
• 959255-78-8 1,3-Dimethoxy-2-[((Z)-propenyl)oxy]-benzene 
• 71186-63-5 2-allyloxy-3-methoxy-phenol 
• 77-78-1 dimethyl sulfate 
• 106-95-6 allyl bromide 

Downstream Products

• 6627-88-9 4-allyl-2,6-dimethoxyphenol 
• 500889-82-7 2-(4-allyl-2,6-dimethoxyphenoxy)acetic acid 
• 1395081-59-0 (S)-3-(2-(4-allyl-2,6-dimethoxyphenoxy)acetyl)-4-isopropyl-5,5-diphenyloxazolidin-2-one 
• 1395081-62-5 (S)-3-((2S,3R)-2-(4-allyl-2,6-dimethoxyphenoxy)-3-hydroxy-3-(3,4,5-trimethoxyphenyl)propanoyl)-4-isopropyl-5,5-diphenyloxazolidin-2-one 
• 1395081-65-8 (1R,2R)-2-(4-allyl-2,6-dimethoxyphenoxy)-1-(3,4,5-trimethoxyphenyl)propane-1,3-diol 
• 1395081-68-1 (2R,3R)-2-(4-allyl-2,6-dimethoxyphenoxy)-3-hydroxy-3-(3,4,5-trimethoxyphenyl)propyl-4-methylbenzenesulfonate 
• 658706-47-9 (1R,2R)-2-[2,6-dimethoxy-4-((E)-prop-1-enyl)phenoxy]-1-(3,4,5-trimethoxyphenyl)propan-1-ol 
• 155696-13-2 Nelumal A 
• 22805-15-8 3-(4-hydroxy-3,5-dimethoxyphenyl) propane-1,2-diol 
• 20736-24-7 1-Syringylpropanol-⁽²⁾ 
• 32883-50-4 1-(3,4,5-trimethoxyphenyl)propan-2-ol 

Relevant articles and documents

Efficient demethylation of aromatic methyl ethers with HCl in water

A green, efficient and cheap demethylation reaction of aromatic methyl ethers with mineral acid (HCl or H2SO4) as a catalyst in high temperature pressurized water provided the corresponding aromatic alcohols (phenols, catechols, pyrogallols) in high yield. 4-Propylguaiacol was chosen as a model, given the various applications of the 4-propylcatechol reaction product. This demethylation reaction could be easily scaled and biorenewable 4-propylguaiacol from wood and clove oil could also be applied as a feedstock. Greenness of the developed methodversusstate-of-the-art demethylation reactions was assessed by performing a quantitative and qualitative Green Metrics analysis. Versatility of the method was shown on a variety of aromatic methyl ethers containing (biorenewable) substrates, yielding up to 99% of the corresponding aromatic alcohols, in most cases just requiring simple extraction as work-up.

Investigating the microwave-accelerated Claisen rearrangement of allyl aryl ethers: Scope of the catalysts, solvents, temperatures, and substrates

The microwave-accelerated Claisen rearrangement of allyl aryl ethers was investigated, in order to gain insight into the scope of the catalysts, solvents, temperatures, and substrates. Among the catalysts examined, phosphomolybdic acid (PMA) was found to greatly accelerate the reaction in NMP, at temperatures ranging from 220 to 300 °C. This method was found to be useful for preparing several intermediates previously reported in the literature using precious metal catalysts such as Au(I), Ag(I), and Pt(II). Additionally, substrates bearing bromo and nitro groups on the aryl portion required careful tailoring of the reaction conditions to avoid complex product profiles.

Lignin depolymerization to monophenolic compounds in a flow-through system

A reductive lignocellulose fractionation in a flow-through system in which pulping and transfer hydrogenolysis steps were separated in time and space has been developed. Without the hydrogenolysis step or addition of trapping agents to the pulping, it is possible to obtain partially depolymerized lignin (21 wt% monophenolic compounds) that is prone to further processing. By applying a transfer hydrogenolysis step 37 wt% yield of lignin derived monophenolic compounds was obtained. Pulp generated in the process was enzymatically hydrolyzed to glucose in 87 wt% yield without prior purification.