4-Methyl-3-nitroaniline

• CAS: 119-32​-4
• Catalog Number: ACM119324
• Category: Main Products
• Molecular Weight: 152.15
• Molecular Formula: C₇H₈N₂O₂
• Appearance: powder

Case Study

4-Methyl-3-Nitroaniline Used in the Synthesis of Propellant Stabilizers

Lundell, Carl E., et al. Chemistryselect, 2017, 2(35), 11673-11676.

Complexes of lead(II) ions with nitroaromatic amines, including 4-methyl-3-nitroaniline and 2-nitrodiphenylamine (NDPA), were prepared to develop alternative ballistic modifiers. The results show that the energy densities of tetrakis(μ3-(4-methyl-3-nitrophenyl imido lead (II))) 1 and bis(2-nitrodiphenyl amido lead(II)) 2 are 30 MJ/L and 38.2 MJ/L, respectively.
Synthesis & structure of tetrakis(μ3-(4-methyl-3-nitrophenyl imido lead (II)))
· The reaction between lead bis(trimethylsilyl)amide and 4-methyl-3-nitroaniline in a 1:1 stoichiometric ratio resulted in the formation of tetrakis(m-(4-methyl-3-nitrophenylimidolead(II))) (1) through the protolysis of hexamethyldisilazane by the acidic amine protons. The initial 1:1 complex further tetramerized into a cubane cluster 1.
· Analysis using X-ray crystallography of the dark red/rust colored crystals showed a distorted cubane structure where Pb and N atoms occupied the corner positions of the cube. The acute interior N-Pb-N angles were around 78° and the interior Pb-N-Pb angles were approximately 101°. The lead corners were protruding and acute, without any observed interaction with a capping ligand. The lead atoms exhibited weak interactions with the tetrahydrofuran (THF) solvent and neighboring nitro groups.

4-Methyl-3-Nitroaniline for the Synthesis of New Amides of N-Methylpiperazine Series

Koroleva, E. V., et al. Russian Journal of Organic Chemistry, 2011, 47, 1556-1563.

The diversity of pharmacological properties and selectivity of biological actions indicate the strong potential of compounds containing benzylpiperazine or piperazine carboxamide fragments. This work synthesizes new functionalized amides based on benzylpiperazine derivatives and substituted benzoic acids, which involves the conversion of 4-methyl-3-nitroaniline (IX) into N-(4-methyl-3-nitrophenyl)-4-(4-methylpiperazin-1-ylmethyl)benzamide (X).
Synthesis procedures compound X from 4-methyl-3-nitroaniline
· Triethylamine (0.6 g, 6 mmol) was introduced with stirring at room temperature to a solution of 4-methyl-3-nitroaniline (IX) (0.5 g, 3 mmol) in 10 ml of THF.
· The temperature of the solution was lowered to 0°C before adding 1.15 g (3.5 mmol) of dihydrochloride VII [4-(4-Methylpiperazin-1-ylmethyl)benzoyl chloride dihydrochloride]. The resulting mixture was stirred at 0°C for 1 hour and then at 50°C for 16 hours.
· After evaporating the mixture, the residue was treated with 10 ml of 10% aqueous sodium hydroxide and extracted with ethyl acetate (3x20 ml). The ethyl acetate extract was dried with Na2SO4, then evaporated under reduced pressure. The remaining substance was purified through recrystallization from chloroform-diethyl ether, yielding 48%.