1,2-Dimethoxybenzene
[CAS# 91-16-7]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Amine
• Name: 1,2-Dimethoxybenzene
• Synonyms: Veratrole; o-Dimethoxybenzene
• Molecular Formula: C₈H₁₀O₂
• Molecular Weight: 138.16
• CAS Registry Number: 91-16-7
• EC Number: 202-045-3
• FEMA: 3799
• SMILES: COC1=CC=CC=C1OC

Properties

• Density: 1.08
• Melting point: 15 °C
• Boiling point: 206-207 °C
• Refractive index: 1.533-1.535
• Flash point: 87 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302
• Safety Statements: P264-P270-P301+P317-P330-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	3	H311

Discovery and Applications

1,2-Dimethoxybenzene, also known as veratrole, is an organic compound with the molecular formula C8H10O2. This aromatic ether has two methoxy groups (-OCH3) attached to adjacent carbon atoms on the benzene ring. Veratrole is a colorless liquid with a pleasant sweet smell that occurs naturally in certain essential oils and plant extracts.

The discovery of 1,2-dimethoxybenzene dates back to the early days of organic chemistry, especially the study of natural products and essential oils. Veratrole was originally isolated from the seeds of the Ferula plant, a plant known for its distinctive aroma. The synthetic preparation of 1,2-dimethoxybenzene involves the methylation of catechol (1,2-dihydroxybenzene) using dimethyl sulfate or methyl iodide in the presence of a base such as potassium carbonate.

1,2-Dimethoxybenzene is an important intermediate in the synthesis of various pharmaceuticals. Its methoxy group provides a site for further chemical modification, making it a valuable building block for the development of drugs with a variety of therapeutic effects. Veratrol derivatives are intensively studied for their potential anti-inflammatory, antioxidant, and anticancer properties.

Veratrol is used in the flavor and fragrance industry for its sweet, floral aroma. It is an ingredient in perfumes, soaps, and cosmetics, providing a pleasant aroma that enhances the product's appeal. In addition, it is used as a flavoring agent in food and beverages, helping to improve the sensory qualities of various products.

In agrochemistry, 1,2-dimethoxybenzene is studied for its potential use in pest control and plant protection. Its derivatives have insecticidal and fungicidal properties and can be used to develop environmentally friendly crop protection agents.

Veratrol is a versatile organic synthetic reagent. It participates in various chemical reactions such as electrophilic aromatic substitution, oxidation, and reduction to produce a wide range of compounds. This reactivity makes it a valuable starting material for the synthesis of complex molecules in academic and industrial research.

1,2-Dimethoxybenzene is used in the synthesis of specialty polymers and resins. Its incorporation into the polymer backbone can enhance material properties such as thermal stability and mechanical strength. These polymers can be used in coatings, adhesives, and advanced materials used in the electronics and aerospace industries.

Veratrol is a reference compound in natural product research. Its structural similarity to various natural compounds allows researchers to study the biosynthetic pathways and ecological roles of these substances in plants.

1,2-Dimethoxybenzene is generally considered to have low toxicity, but it should be handled with care. It can cause skin and eye irritation, so appropriate protective equipment such as gloves and goggles should be worn when handling the substance. Proper ventilation is also recommended to avoid inhalation of vapors.

References

2002. Microbial Enantioselective Ester Hydrolysis for the Preparation of Optically Active 4,1-Benzoxazepine-3-acetic Acid Derivatives as Squalene Synthase Inhibitors. Chemical and Pharmaceutical Bulletin, 50(1).
DOI: 10.1248/cpb.50.59

2003. Mechanistic Features of Lignin Peroxidase-catalyzed Oxidation of Substituted Phenols and 1,2-Dimethoxyarenes. The Journal of biological chemistry, 278(41).
DOI: 10.1074/jbc.m303918200

2013. Biohydrogen production from CO-rich syngas via a locally isolated Rhodopseudomonas palustris PT. Bioprocess and Biosystems Engineering, 37(3).
DOI: 10.1007/s00449-013-1064-6