Nitroaromatic guanidine salts, such as (2-Methyl-5-nitrophenyl)guanidine Nitrate (CAS: 152460-08-7), are a class of chemical compounds that blend the characteristics of nitroaromatics with the basicity and reactive potential of guanidine. These compounds find significant use as intermediates in the synthesis of pharmaceuticals, agrochemicals, and other specialized organic chemicals. A thorough understanding of their properties, reactivity, and safe handling procedures is crucial for industrial operations.

Chemical Structure and Key Properties

The structure of (2-Methyl-5-nitrophenyl)guanidine Nitrate features a phenyl ring substituted with a methyl group and a nitro group, attached to a guanidine moiety, balanced by a nitrate anion. This combination dictates its behavior:

  • Nitro Group (NO₂): This electron-withdrawing group influences the electron density of the aromatic ring, often making it susceptible to nucleophilic aromatic substitution under certain conditions and contributing to potential energetic properties in some derivatives.
  • Guanidine Group (C(NH₂)₂NH₂): As a strong organic base, the guanidine moiety readily forms resonance-stabilized cations. This basicity is key to its use as a synthetic intermediate, facilitating reactions such as deprotonation or salt formation.
  • Nitrate Anion (NO₃⁻): The nitrate counterion contributes to the salt's overall stability and solubility. In some highly nitrated compounds, nitrate groups can contribute to energetic characteristics.

Physically, (2-Methyl-5-nitrophenyl)guanidine Nitrate typically presents as an off-white to yellow crystalline solid with a notable melting point of around 218-219°C. Its solubility in water is generally moderate, and it is often stored under inert gas to maintain stability.

Synthesis Considerations

The synthesis of such compounds often involves careful control of reaction conditions. Common methods include the reaction of substituted anilines with cyanamide derivatives under acidic conditions, followed by salt formation with nitric acid. Alternatively, nitration of existing guanidine derivatives can be employed. Industrial production necessitates optimized processes for yield, purity, and safety, especially when dealing with nitro compounds.

Reactivity and Applications

The reactivity of (2-Methyl-5-nitrophenyl)guanidine Nitrate stems from its functional groups. The nitro group can be reduced to an amine, opening pathways for further functionalization. The guanidine group can undergo various condensation reactions. Its primary application as a pharmaceutical intermediate, particularly in the synthesis of imatinib and other kinase inhibitors, highlights its value in complex organic synthesis. For those looking to buy this intermediate, understanding its reaction profile is key to successful downstream synthesis.

Safety and Handling Precautions

Handling nitroaromatic guanidine salts requires adherence to strict safety protocols:

  • Personal Protective Equipment (PPE): Always wear appropriate PPE, including chemical-resistant gloves, safety goggles, and protective clothing, to prevent skin and eye contact.
  • Ventilation: Ensure adequate ventilation in work areas to prevent inhalation of dust or vapors.
  • Storage: Store in a cool, dry, well-ventilated area, away from incompatible materials such as strong oxidizing agents or reducing agents. Storage under an inert atmosphere is often recommended to preserve product integrity.
  • Fire Hazards: While not always highly flammable, nitro compounds can pose risks under certain conditions. Keep away from ignition sources.
  • Disposal: Dispose of waste materials in accordance with local, regional, and national regulations, typically through licensed chemical waste disposal services.

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