3-(difluoromethyl)-4-nitro-1H-pyrazole
[CAS# 1789048-54-9]

Identification

• Classification: Organic raw materials >> Heterocyclic compound
• Name: 3-(difluoromethyl)-4-nitro-1H-pyrazole
• Synonyms: 5-(difluoromethyl)-4-nitro-1H-pyrazole
• Molecular Formula: C₄H₃F₂N₃O₂
• Molecular Weight: 163.08
• CAS Registry Number: 1789048-54-9
• EC Number: 884-504-3
• SMILES: C1=NNC(=C1[N+](=O)[O-])C(F)F

Properties

• Density: 1.6±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.519, Calc.^*
• Boiling Point: 380.3±37.0 °C (760 mmHg), Calc.^*
• Flash Point: 183.8±26.5 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H312-H315-H319-H332-H335
• Safety Statements: P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H302
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	4	H312
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

3-(Difluoromethyl)-4-nitro-1H-pyrazole is a heterocyclic compound containing both a difluoromethyl (-CF2H) and a nitro (-NO2) functional group. The presence of these groups imparts significant chemical and biological properties, making the compound relevant in various research and industrial applications. The pyrazole core is a well-known structural motif in pharmaceuticals, agrochemicals, and materials science due to its stability and reactivity.

The discovery of substituted pyrazoles, including those with fluorine-containing functional groups, has been an area of interest in organic and medicinal chemistry for several decades. Fluorinated pyrazoles have been studied for their ability to enhance the metabolic stability and bioactivity of compounds. The introduction of a difluoromethyl group to the pyrazole ring can modify its electronic properties, influencing interactions with biological targets and improving pharmacokinetic properties.

One of the primary applications of 3-(difluoromethyl)-4-nitro-1H-pyrazole is in the development of pharmaceutical and agrochemical agents. Fluorinated heterocycles are frequently found in bioactive molecules, and the difluoromethyl substituent is known to improve lipophilicity and membrane permeability. These properties make the compound a useful intermediate in the synthesis of active pharmaceutical ingredients (APIs) and pesticide candidates.

In agrochemistry, pyrazole derivatives, particularly those bearing electron-withdrawing groups like nitro and difluoromethyl, have been explored for their herbicidal, fungicidal, and insecticidal properties. Such compounds often act by inhibiting key enzymatic processes in target organisms, disrupting their metabolism or growth.

Beyond pharmaceuticals and agrochemicals, 3-(difluoromethyl)-4-nitro-1H-pyrazole has applications in material science. Fluorinated pyrazoles are used in the design of energetic materials due to their high nitrogen content and favorable detonation properties. The presence of the nitro group further enhances the compound’s potential as a precursor for high-energy materials.

Synthetic approaches for this compound generally involve selective fluorination and nitration reactions. Researchers have explored various methodologies to introduce the difluoromethyl and nitro groups onto the pyrazole ring in a controlled manner. Advances in fluorination chemistry have facilitated the efficient synthesis of difluoromethylated heterocycles, allowing for broader applications in drug discovery and material development.

Overall, 3-(difluoromethyl)-4-nitro-1H-pyrazole is a valuable compound with applications in pharmaceuticals, agrochemicals, and materials science. Its unique structural features contribute to its versatility in organic synthesis and bioactive molecule development.

References

Mainolfi, N., Ji, N., Weiss, M. M. et al. (2020). IRAK degraders and uses thereof. WO-2020264499-A1, 2020-12-30.
Priority Date: 2019-06-28.

Mainolfi, N., Ji, N., Kluge, A. F. et al. (2020). IRAK degraders and uses thereof. WO-2020113233-A1, 2020-06-04.
Priority Date: 2018-11-30.

Mainolfi, N., Ji, N., Weiss, M. M. et al. (2022). IRAK disintegrants and uses thereof. KR-20220032063-A, 2022-03-15.
Priority Date: 2019-06-28.