2,3-Dimethoxybenzaldehyde
[CAS# 86-51-1]

Identification

• Classification: Chemical reagent >> Organic reagent >> Aromatic aldehyde (containing acetal, hemiacetal)
• Name: 2,3-Dimethoxybenzaldehyde
• Molecular Formula: C₉H₁₀O₃
• Molecular Weight: 166.18
• CAS Registry Number: 86-51-1
• EC Number: 201-677-7
• SMILES: COC1=CC=CC(=C1OC)C=O

Properties

• Density: 1.1±0.1 g/cm³, Calc.^*
• Melting point: 48-52 °C (Expl.)
• Index of Refraction: 1.534, Calc.^*
• Boiling Point: 266.7±20.0 °C (760 mmHg), Calc.^*, 137 °C (12 mmHg) (Expl.)
• Flash Point: 105.8±8.2 °C, Calc.^*, 113 °C (Expl.)

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety 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
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

2,3-Dimethoxybenzaldehyde is an organic compound that belongs to the class of methoxy-substituted aldehydes. It is characterized by the presence of two methoxy groups (-OCH3) at the 2- and 3-positions on the benzene ring, and an aldehyde group (-CHO) at the 1-position. The compound has attracted attention due to its distinctive chemical structure, which makes it useful in a variety of synthetic applications. The discovery of 2,3-dimethoxybenzaldehyde dates back to early research on the modification of aromatic aldehydes with methoxy groups, which are known to alter the electronic properties of the parent molecule. This modification enhances the reactivity of the aldehyde group and provides the compound with unique characteristics.

The synthesis of 2,3-dimethoxybenzaldehyde typically involves the methoxylation of benzaldehyde using methanol or other methylating reagents in the presence of an acid catalyst. The methoxy groups are introduced at the ortho positions relative to the aldehyde group, leading to the formation of the desired 2,3-dimethoxy substitution pattern. This reaction is often carried out under mild conditions to preserve the integrity of the aldehyde functionality. The resulting product can be further modified to create a variety of derivatives that find use in different chemical reactions.

2,3-Dimethoxybenzaldehyde has a broad range of applications, particularly in organic synthesis. One of its most notable uses is as an intermediate in the production of various pharmaceuticals and agrochemicals. The methoxy groups on the aromatic ring significantly influence the reactivity and selectivity of the compound in reactions such as Friedel-Crafts acylation and nucleophilic substitution. This makes 2,3-dimethoxybenzaldehyde a valuable building block for the synthesis of more complex organic molecules.

Another significant application of 2,3-dimethoxybenzaldehyde is in the field of materials science, where it is used in the preparation of organic semiconductors and dyes. Its ability to form conjugated structures due to the electron-donating nature of the methoxy groups enhances its role in optoelectronic devices. Additionally, the compound is sometimes used in the synthesis of polymers and resins, which find applications in coatings and electronic materials.

Furthermore, 2,3-dimethoxybenzaldehyde has shown promise as a precursor in the development of natural product analogs. For instance, it has been investigated for its potential in the synthesis of certain flavonoids and other bioactive molecules. Its unique structural features, including the aldehyde and methoxy groups, provide an opportunity to modify these molecules to optimize their biological activity for use in medicinal chemistry.

In conclusion, 2,3-dimethoxybenzaldehyde is a versatile and important chemical compound in organic chemistry. Its applications span a wide range of industries, from pharmaceuticals to materials science, making it a valuable intermediate for the synthesis of a variety of functional compounds. The continuing development of synthetic methods for modifying and utilizing this compound will likely expand its utility in future research and industrial applications.

References

2019. Synthesis and Cardiotropic Activity of Linear Methoxyphenyltriazaalkanes. Pharmaceutical Chemistry Journal, 53(6).
DOI: 10.1007/s11094-019-02027-7

2018. One-Step Three-Component Synthesis of New 2,5,6,7-Functionalized 5,8-Dihydropyrido-[2,3-d]pyrimidin-4(3H)-ones. Russian Journal of Organic Chemistry, 54(1).
DOI: 10.1134/s1070428018010104

2016. Synthesis and Antiviral Activity of Hydroxy-Substituted Benzaldehydes and Related Compounds. Pharmaceutical Chemistry Journal, 50(3).
DOI: 10.1007/s11094-016-1414-1