1-Methyl-4-acetylpyrazole
[CAS# 37687-18-6]

Identification

• Classification: Organic raw materials >> Aryl compounds
• Name: 1-Methyl-4-acetylpyrazole
• Synonyms: 1-(1-Methyl-1H-pyrazol-4-yl)ethanone; 1-(1-Methyl-1H-pyrazol-4-yl)ethan-1-one
• Molecular Formula: C₆H₈N₂O
• Molecular Weight: 124.14
• CAS Registry Number: 37687-18-6
• EC Number: 675-437-9
• SMILES: CC(=O)C1=CN(N=C1)C

Properties

• Solubility: Sparingly soluble (19 g/L) (25 ºC), Calc.^*
• Density: 1.11±0.1 g/cm³ (20 ºC 760 Torr), Calc.^*
• Boiling point: 221.0±13.0 ºC 760 mmHg (Calc.)^*
• Flash point: 87.4±19.8 ºC (Calc.)^*
• Index of refraction: 1.543 (Calc.)^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233,

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2A	H319
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2	H319

Discovory and Applicatios

1-Methyl-4-acetylpyrazole is an organic compound that belongs to the class of pyrazole derivatives. It features a pyrazole ring with a methyl group at the 1-position and an acetyl group at the 4-position. This simple yet functionalized structure plays a crucial role in a variety of chemical and pharmaceutical applications.

The compound is synthesized through straightforward organic reactions, typically involving the methylation of 4-acetylpyrazole or a related precursor. The methyl group is introduced at the 1-position of the pyrazole ring, which stabilizes the molecule and can affect its reactivity and solubility. The acetyl group at the 4-position provides a functional site for further chemical modifications, making 1-methyl-4-acetylpyrazole a versatile intermediate in synthetic chemistry.

1-Methyl-4-acetylpyrazole is widely utilized in pharmaceutical research due to the bioactivity associated with pyrazole derivatives. The pyrazole ring is a well-known scaffold in medicinal chemistry, and the introduction of various substituents, such as the methyl and acetyl groups, can significantly alter the pharmacological properties of the compound. Pyrazoles are often studied for their potential as anti-inflammatory, antimicrobial, and anticancer agents, and derivatives like 1-methyl-4-acetylpyrazole may exhibit similar or enhanced activities compared to the parent compounds.

In addition to its pharmaceutical potential, 1-methyl-4-acetylpyrazole serves as a valuable intermediate in the synthesis of more complex pyrazole-based compounds. The acetyl group at the 4-position can undergo nucleophilic substitution or condensation reactions, allowing the creation of a variety of derivatives with tailored functional properties. For instance, the compound can be used to synthesize pyrazole derivatives with additional functional groups, which may have improved biological activity or different chemical properties suitable for specific applications.

Another application of 1-methyl-4-acetylpyrazole is in the development of agrochemicals. As with many pyrazole derivatives, it has the potential to be used as a building block for herbicides, fungicides, or insecticides. The pyrazole ring structure is often found in agrochemicals due to its ability to interact with biological systems in a selective and targeted manner. The methyl and acetyl substitutions can fine-tune the compound’s interactions with pests or pathogens, enhancing its effectiveness as a crop protection agent.

Furthermore, 1-methyl-4-acetylpyrazole can be used in the synthesis of specialty chemicals and materials. The pyrazole structure is stable and can undergo a variety of chemical reactions, allowing it to be incorporated into larger molecules or polymeric materials. The compound’s functional groups make it a useful precursor for the synthesis of dyes, pigments, and other organic materials, as well as a ligand in coordination chemistry, where its donor sites may bind to metal ions.

In summary, 1-methyl-4-acetylpyrazole is a versatile and functionalized pyrazole derivative with applications in pharmaceuticals, agrochemicals, and material science. Its simple structure, which consists of a methyl group at the 1-position and an acetyl group at the 4-position, makes it a valuable intermediate in the synthesis of bioactive compounds, agrochemical agents, and specialty materials. The ability to further modify its functional groups allows researchers to explore new chemical properties and expand its range of potential applications in various fields of chemistry and industry.

References

2013. Direct Electrophilic Acylation of N-Substituted Pyrazoles by Anhydrides of Carboxylic Acids. Synthesis, 45(16).
DOI: 10.1055/s-0033-1338923

2021. Synthesis of Quinoxaline Derivatives as Intermediates to Obtain Erdafitinib. Pharmaceutical Chemistry Journal, 55(9).
DOI: 10.1007/s11094-021-02521-x