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Send EmailDimethyl Pyrazole, 3,4-Dimethylpyrazole, DMP, Pyrazole, 3,4-DMP, Dimethylpyrazole, 2820-37-3
🧪 3,4-Dimethylpyrazole (DMP) – Chemical Profile
| Property | Value |
|---|---|
| IUPAC Name | 3,4-Dimethyl-1H-pyrazole |
| CAS Number | 2820-37-3 |
| Molecular Formula | C₅H₈N₂ |
| Molecular Weight | 96.13 g/mol |
| Appearance | Light yellow solid |
| Structure | Pyrazole ring with methyl groups at positions 3 and 4 |
| EC Number | 429-130-1 |
| ChemSpider ID | 121391 |
⚗️ Applications
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DMPP Synthesis: Reacts with phosphoric acid to form 3,4-Dimethylpyrazole phosphate (DMPP), a nitrification inhibitor in fertilizers.
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Agrochemical Intermediate: Used in the synthesis of plant protection agents and nitrogen stabilizers.
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Pharmaceutical R&D: Pyrazole derivatives are explored for anti-inflammatory and antimicrobial properties.
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Polymer Additives: Occasionally used in specialty formulations requiring nitrogen-containing heterocycles.
🏭 Production Notes
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Synthesis Route: Typically involves condensation of acetylacetone with hydrazine derivatives.
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Storage: Stable under dry, cool conditions; sensitive to moisture and oxidation.
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Packaging: Often supplied in 25 kg fiber drums or PE-lined bags.
🏭 Production of 3,4-Dimethylpyrazole (DMP)
🧪 Chemical Identity
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IUPAC Name: 3,4-Dimethyl-1H-pyrazole
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CAS Number: 2820-37-3
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Molecular Formula: C₅H₈N₂
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Molecular Weight: 96.13 g/mol
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Appearance: Pale yellow crystalline solid
⚗️ Synthesis Process Overview
1️⃣ Starting Materials
| Compound | Function |
|---|---|
| Acetylacetone (2,4-Pentanedione) | Provides the carbon backbone |
| Hydrazine Hydrate (N₂H₄·H₂O) | Supplies nitrogen atoms for the pyrazole ring |
| Solvent | Water, ethanol, or DMF depending on process |
| Catalyst (optional) | Acid catalyst may be used to accelerate reaction |
2️⃣ Reaction Steps
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Condensation: Acetylacetone reacts with hydrazine in a 1:1 molar ratio.
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Cyclization: The pyrazole ring forms with methyl groups at positions 3 and 4.
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Purification: Crystallization, filtration, or solvent extraction removes impurities.
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Drying: Final product is dried under vacuum or ambient conditions.
3️⃣ Typical Conditions
| Parameter | Value |
|---|---|
| Temperature | 60–80 °C |
| Reaction Time | 4–6 hours |
| pH | Neutral to slightly acidic |
| Reactor Type | Glass-lined or stainless steel reactor |
🧾 3,4-Dimethylpyrazole – Synonyms and Identifiers
| Type | Name / Code |
|---|---|
| IUPAC Name | 3,4-Dimethyl-1H-pyrazole |
| Common Name | 3,4-Dimethylpyrazole (DMP) |
| Abbreviations | DMP, 3,4-DMP, Dimethylpyrazole |
| CAS Number | 2820-37-3 |
| EC Number | 429-130-1 |
| EINECS Number | 220-532-7 |
| Molecular Formula | C₅H₈N₂ |
| Molecular Weight | 96.13 g/mol |
| ChemSpider ID | 121391 |
| PubChem CID | 13843 |
| SMILES Notation | CC1=C(NN=C1C) |
| InChIKey | QKXKXJIEISDUBI-UHFFFAOYSA-N |
| Trade Names (varies by supplier) | DMP, Pyrazole, 3,4-DMP, Dimethylpyrazole |
🔄 Alternatives to DMPP (3,4-Dimethylpyrazole phosphate)
| Compound | CAS Number | Duration | Application | Notes |
|---|---|---|---|---|
| DCD (Dicyandiamide) | 461-58-5 | 4–6 weeks | Granular fertilizers | Cost-effective, widely used |
| NPPT (Nitrapyrin) | 1929-82-4 | 6–8 weeks | Liquid fertilizers, corn, wheat | Volatile, temperature-sensitive |
| DMPSA (3,4-Dimethylpyrazole succinic acid) | 202842-98-6 | 8–12 weeks | Similar to DMPP | Environmentally friendly, low leaching risk |
| NBPT (N-(n-butyl) thiophosphoric triamide) | 94317-64-3 | 1–2 weeks | Urea-based fertilizers | Urease inhibitor; reduces volatilization |
| DMPB (3,5-Dimethylpyrazole glyceroborate) | — | 6–10 weeks | Ammonium sulfate blends | New-generation inhibitor; tested in Türkiye |
📌 Application Notes
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DCD: Most economical option; suppresses microbial nitrification.
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NPPT: Targets Nitrosomonas bacteria; requires careful handling in warm climates.
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DMPSA: Structurally similar to DMPP; longer-lasting and eco-friendly.
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NBPT: Not a nitrification inhibitor — works by stabilizing urea nitrogen.
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DMPB: Evaluated in Turkish academic trials (e.g., Erciyes University); shown to improve phosphorus uptake and nitrogen retention.
