3,5-Dimethoxytoluene
[CAS# 4179-19-5]

Identification

• Classification: Chemical reagent >> Organic reagent >> Aromatic hydrocarbon reagent
• Name: 3,5-Dimethoxytoluene
• Synonyms: 1,3-dimethoxy-5-methylbenzene
• Molecular Formula: C₉H₁₂O₂
• Molecular Weight: 152.19
• CAS Registry Number: 4179-19-5
• EC Number: 224-048-9
• SMILES: CC1=CC(=CC(=C1)OC)OC

Properties

• Density: 1.039
• Boiling point: 244 ºC
• Refractive index: 1.522
• Flash point: 215 ºF

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovory and Applicatios

3,5-Dimethoxytoluene, an aromatic compound with the molecular formula C10H14O2, is characterized by its methoxy groups attached to a toluene ring. This compound features two methoxy groups located at the 3 and 5 positions relative to the methyl group on the toluene ring. Its discovery and subsequent applications highlight its significance in both organic synthesis and industrial processes.

The synthesis of 3,5-dimethoxytoluene involves a straightforward method where methoxy groups are introduced to a toluene substrate. Typically, this is achieved through methylation reactions using methoxy sources such as methyl iodide in the presence of a base, or through direct alkylation techniques that modify the toluene ring structure. The compound was first synthesized and characterized in the early 20th century, and its unique structure quickly attracted attention due to its potential applications in various fields.

One of the primary applications of 3,5-dimethoxytoluene is in organic synthesis as an intermediate for producing more complex molecules. Its methoxy groups provide sites for further chemical modifications, making it a useful building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals. For example, the compound serves as a precursor in the synthesis of more complex aromatic compounds used in medicinal chemistry. The presence of methoxy groups can also influence the reactivity and stability of the molecule, allowing chemists to tailor reactions for specific outcomes.

In the field of pharmaceuticals, 3,5-dimethoxytoluene is utilized in the synthesis of various drug candidates. Its ability to modify the electronic and steric properties of the toluene ring is exploited to create derivatives with enhanced biological activity or improved pharmacokinetic properties. The compound has been incorporated into the synthesis of drugs targeting diverse therapeutic areas, including cancer and cardiovascular diseases, where the methoxy groups can modulate the interaction of the drug with biological targets.

Additionally, 3,5-dimethoxytoluene finds applications in the production of flavor and fragrance compounds. Its aromatic nature and methoxy substituents contribute to the formation of fragrances and flavorings used in the food and cosmetic industries. The compound is often used as a precursor to synthesize other aromatic compounds that impart specific sensory attributes to products. For instance, it can be converted into substances that enhance the aroma or taste profile of various consumer goods.

The compound's role in materials science is also notable. 3,5-Dimethoxytoluene is utilized in the development of new materials, such as polymers and resins. Its methoxy groups can participate in polymerization reactions, leading to the formation of materials with unique properties, such as increased stability or specific optical characteristics. These materials are employed in a variety of applications, including coatings, adhesives, and advanced composites.

Research into the environmental and safety aspects of 3,5-dimethoxytoluene has shown that it is generally considered to be of low toxicity. However, as with all chemicals, appropriate handling and safety measures are required during its use and synthesis. Studies on its environmental impact are ongoing to ensure that its applications do not pose risks to ecosystems or human health.

Overall, 3,5-dimethoxytoluene is a versatile compound with significant applications in organic synthesis, pharmaceuticals, flavor and fragrance production, and materials science. Its methoxy groups and aromatic structure provide valuable properties that facilitate the development of various chemical products and materials.

References

2002. Biosynthesis of the major scent components 3,5-dimethoxytoluene and 1,3,5-trimethoxybenzene. FEBS Letters. DOI: 10.1016/s0014-5793(02)02956-3

2019. Synthesis of (-)-Perezoperezone. Synfacts. DOI: 10.1055/s-0039-1691319

2020. De Novo Transcriptomics Analysis of the Floral Scent of Chinese Narcissus. Tropical Plant Biology. DOI: 10.1007/s12042-020-09253-4