2,5-Dimethoxybenzohydrazide
[CAS# 17894-25-6]

Identification

• Classification: Chemical reagent >> Organic reagent >> Hydrazine
• Name: 2,5-Dimethoxybenzohydrazide
• Molecular Formula: C₉H₁₂N₂O₃
• Molecular Weight: 196.20
• CAS Registry Number: 17894-25-6
• EC Number: 674-289-2
• SMILES: COC1=CC(=C(C=C1)OC)C(=O)NN

Properties

• Density: 1.2±0.1 g/cm³, Calc.^*, 1.189 g/mL
• Melting point: 89-91 ºC
• Index of Refraction: 1.545, Calc.^*

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

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

2,5-Dimethoxybenzohydrazide is an organic compound that has gained attention in recent years due to its diverse applications in the fields of pharmaceuticals and agrochemicals. This compound, characterized by the presence of two methoxy groups and a hydrazide functional group, was first synthesized in the early 2000s as part of research aimed at developing new hydrazone derivatives with potential biological activities. Its unique structure enables it to exhibit a range of chemical properties, making it a valuable building block in synthetic organic chemistry.

The synthesis of 2,5-dimethoxybenzohydrazide typically involves the reaction of 2,5-dimethoxybenzoic acid with hydrazine hydrate. This process not only yields the hydrazide derivative but also opens the door to further modifications, allowing chemists to explore the structure-activity relationships of various derivatives. The presence of the methoxy groups enhances the solubility of the compound in organic solvents, facilitating its use in various applications.

One of the primary applications of 2,5-dimethoxybenzohydrazide is in the pharmaceutical industry, where it has been investigated for its potential as an anti-cancer agent. Preliminary studies have demonstrated that this compound can inhibit the growth of specific cancer cell lines, making it a candidate for further research and development in oncology. The mechanism of action is thought to involve the modulation of various cellular pathways, although detailed studies are still underway to elucidate its specific effects.

In addition to its anti-cancer properties, 2,5-dimethoxybenzohydrazide has shown promise as a building block in the synthesis of various bioactive molecules. Researchers have explored its use in the preparation of hydrazones and azo compounds, which are known for their biological activities, including antimicrobial and antifungal properties. This versatility in synthetic applications makes 2,5-dimethoxybenzohydrazide an important compound for medicinal chemistry and drug discovery.

Moreover, the compound's ability to form stable complexes with transition metals has garnered interest in coordination chemistry. These metal complexes can exhibit unique catalytic properties, making them potential candidates for applications in organic synthesis and material science. By modifying the coordination environment through the use of 2,5-dimethoxybenzohydrazide, researchers can design catalysts with tailored properties for specific reactions.

Another significant application of 2,5-dimethoxybenzohydrazide is in the field of agrochemicals. Its derivatives have been studied for use as plant growth regulators and as agents for pest control. The ability to enhance plant growth or provide protection against pests contributes to sustainable agricultural practices and improves crop yields.

While the potential of 2,5-dimethoxybenzohydrazide is significant, it is essential to consider the safety and environmental aspects associated with its use. As with many chemical compounds, proper handling and adherence to regulatory guidelines are crucial to minimize health risks. Ongoing research aims to evaluate the environmental impact of its derivatives and to develop safer alternatives where necessary.

In summary, 2,5-dimethoxybenzohydrazide is a versatile compound that has found applications in pharmaceuticals, agrochemicals, and coordination chemistry. Its discovery marked a significant advancement in the search for new bioactive molecules and catalysts. As research continues to unveil its full potential, this compound remains a valuable asset in the fields of organic chemistry and material science.