1,3-Dimethylpyrazole
[CAS# 694-48-4]

Identification

• Classification: Chemical pesticide >> Herbicide >> Herbicide intermediate
• Name: 1,3-Dimethylpyrazole
• Molecular Formula: C₅H₈N₂
• Molecular Weight: 96.13
• CAS Registry Number: 694-48-4
• EC Number: 689-662-5
• SMILES: CC1=NN(C=C1)C

Properties

• Density: 1.0±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.519, Calc.^*
• Boiling Point: 140.2±9.0 °C (760 mmHg), Calc.^*, 136-138 °C (Expl.)
• Flash Point: 38.6±18.7 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS02;GHS07 Warning
• Risk Statements: H226-H315-H319-H335
• Safety Statements: P210-P233-P240-P241-P242-P243-P261-P264-P264+P265-P271-P280-P302+P352-P303+P361+P353-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P370+P378-P403+P233-P403+P235-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Flammable liquids	Flam. Liq.	3	H226
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

1,3-Dimethylpyrazole is an organic compound that belongs to the pyrazole class of heterocyclic compounds. It is characterized by a pyrazole ring structure with two methyl groups attached to the nitrogen atoms in positions 1 and 3. This structure is similar to other pyrazoles but differs due to the presence of the methyl groups, which influence its chemical properties and reactivity.

The discovery of 1,3-dimethylpyrazole is part of the broader exploration of pyrazole derivatives, which have attracted significant attention due to their diverse chemical reactivity and potential biological activities. Pyrazoles, including 1,3-dimethylpyrazole, are synthesized via methods that typically involve the reaction of hydrazine derivatives with α,β-unsaturated carbonyl compounds, followed by methylation.

1,3-Dimethylpyrazole finds utility in various industrial and scientific applications. One of the primary applications is in the field of agriculture, particularly as a precursor or intermediate in the synthesis of herbicides. The compound has been studied as a potential building block for the preparation of agricultural chemicals due to its ability to participate in reactions that lead to the formation of more complex molecules with biological activity.

In addition to its agricultural applications, 1,3-dimethylpyrazole is used in organic synthesis, particularly as a reagent in the preparation of other pyrazole derivatives. Pyrazoles, including 1,3-dimethylpyrazole, are valuable intermediates in the synthesis of pharmaceuticals and agrochemicals. This compound is involved in reactions that lead to the creation of bioactive molecules, some of which may possess antimicrobial, anticancer, or anti-inflammatory properties.

Moreover, 1,3-dimethylpyrazole is employed in laboratory settings for the preparation of other chemicals. The compound has been studied for its role in the synthesis of metal complexes, where it can act as a ligand due to its nitrogen atoms. This characteristic makes it useful in the design of coordination compounds, which have potential applications in materials science and catalysis.

1,3-Dimethylpyrazole also plays a role in the synthesis of certain pharmaceuticals, particularly those that require pyrazole or pyrazole-based structures. While the direct medicinal use of 1,3-dimethylpyrazole itself may not be widespread, its role as an intermediate in the synthesis of more complex pharmaceutical compounds highlights its importance in medicinal chemistry.

In summary, 1,3-dimethylpyrazole is a pyrazole derivative with significant applications in organic synthesis and agriculture. It is used primarily as an intermediate in the production of herbicides and other chemicals. Its role in the preparation of metal complexes and pharmaceuticals further underscores its utility in various fields of chemical research and industrial applications.

References

1970. Synthesis of pyrazoles by condensation of unsymmetrical dialkylhydrazines withβ-chlorovinyl ketones. Chemistry of Heterocyclic Compounds, 6(10).
DOI: 10.1007/bf00755088

2011. Novel method for the synthesis of 4-formyl-1,3-dimethylpyrazole. Chemistry of Heterocyclic Compounds, 47(8).
DOI: 10.1007/s10593-011-0873-2

2014. The Reactivity Trends in Electrochemical Chlorination and Bromination of N-Substituted and N-Unsubstituted Pyrazoles. Chemistry of Heterocyclic Compounds, 49(10).
DOI: 10.1007/s10593-014-1411-9