N-Methyl-4-nitroaniline: properties, applications and safety

General Description

N-Methyl-4-nitroaniline (MNMA) is a valuable compound with distinct properties. It appears as a yellow crystalline solid and has a solid-state at room temperature. It exhibits limited solubility in water but dissolves in organic solvents. MNMA contains a nitro group, making it reactive and suitable for various chemical reactions. It serves as a building block for organic synthesis, producing derivatives used in pharmaceuticals and agrochemicals. MNMA is also used as an additive in polymer formulations to enhance thermal and UV stability. Additionally, it plays a role in explosives production, aiding in sensitivity control. However, MNMA is potentially hazardous and requires appropriate safety measures when handling.

Figure 1. N-Methyl-4-nitroaniline

Properties

N-Methyl-4-nitroaniline is a valuable compound known for its distinct properties. It appears as a solid crystalline substance with a yellow or brownish-yellow color. With a melting point of 180-182°C, it maintains a solid state at room temperature, showcasing its stability. It exhibits limited solubility in water but readily dissolves in organic solvents such as ethanol and ether. Chemically, N-Methyl-4-nitroaniline possesses a nitro group (–NO2) in its structure, rendering it reactive and prone to reduction reactions that yield amino derivatives. This reactivity makes it a valuable precursor for the synthesis of diverse compounds. Being classified as an aromatic amine, it belongs to a crucial class of compounds used as building blocks in the creation of dyes, pharmaceuticals, and agrochemicals. The electron-withdrawing nature of the nitro group in N-Methyl-4-nitroaniline imparts electrophilic aromatic substitution reactivity to the compound. This property enables its application in various organic transformations, expanding its utility in different chemical processes. In summary, N-Methyl-4-nitroaniline exhibits unique properties like its solid-state at room temperature, solubility in organic solvents, and reactivity towards reduction and electrophilic aromatic substitution reactions. These characteristics make it indispensable in the synthesis of dyes, drugs, and other fine chemicals, showcasing its versatility and importance in the field of organic chemistry. ¹

Applications

N-Methyl-4-nitroaniline is a yellow crystalline solid widely used in various industrial applications. Its versatility lies in its role as a building block for organic synthesis, where it can undergo several chemical reactions to yield different derivatives. These derivatives are utilized in pharmaceuticals, agrochemicals, and other organic synthesis processes. MNMA finds application in polymer stabilizers, particularly when incorporated as an additive in polymer formulations. Polymers like polyvinyl chloride (PVC) can experience degradation when exposed to heat or sunlight. By adding MNMA, the thermal and UV stability of these polymers can be enhanced, improving their overall lifespan. This makes them suitable for use in construction, electrical insulation, and other industries. Additionally, MNMA plays a role in the production of explosives as a component in certain formulations. With its ability to sensitize or stabilize high-energy materials such as propellants and pyrotechnics, MNMA aids in controlling the sensitivity, ignition, and combustion properties of these compounds. This ensures their safe handling and controlled release of energy. Overall, N-Methyl-4-nitroaniline is a valuable compound with applications ranging from organic synthesis to analytical chemistry, polymer stabilization, and explosives production. Its versatility and diverse uses make it an important ingredient in various industrial processes. ²

Safety

N-Methyl-4-nitroaniline is a potentially hazardous substance. Exposure to high concentrations of this substance may cause irritation of the respiratory tract, nose, and eyes. Prolonged contact with skin may cause dermatitis and other skin problems. In addition, N-methyl-4-nitroaniline has been shown to have genotoxic and carcinogenic effects in animal experiments. Therefore, it is necessary to take appropriate safety measures when handling this substance, such as using personal protective equipment and ensuring good ventilation to minimize exposure. Workers should also receive regular health checks and periodic evaluations of the hazards associated with this substance. Additionally, it is important to comply with relevant regulations and safety standards to ensure the safe use and handling of N-methyl-4-nitroaniline. ³

Reference

1. Boddu VM, Abburi K, Maloney SW, Damavarapu R. Physicochemical properties of an insensitive munitions compound, N-methyl-4-nitroaniline (MNA). J Hazard Mater, 2008, 155(1-2):288-294.

2. Olivares CI, Wang J, Luna CD, Field JA, Abrell L, Sierra-Alvarez R. Continuous treatment of the insensitive munitions compound N-methyl-p-nitro aniline (MNA) in an upflow anaerobic sludge blanket (UASB) bioreactor. Chemosphere, 2016, 144:1116-1122.

3. SAFETY DATA SHEET: N-Methyl-4-nitroaniline. Thermo Fisher SCIENTIFIC, 2020, Cat No:A15548.

You may like