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Abstract
This article presents a comprehensive overview of MDP2NP, a key precursor for MDA and MDMA production, including its general information, physico-chemical properties, chemical reactions, synthesis of MDP2NP, conclusion and bibliography.
General Information About MDP2NP [1-4]
Other synonyms names of MDP2NP are: 5-(2-Nitroprop-1-en-1-yl)benzo[d][1,3]dioxole; 5-(2-Nitro-1-propenyl)-1,3-benzodioxole; 3,4-methylenedioxyphenyl-2-nitropropene; MDP2NP; 1-MPNP
IUPAC Names of MDP2NP: 5-(2-nitroprop-1-enyl)-1,3-benzodioxole
CAS number is 5438-41-5
Physico-Chemical Properties of MDP2NP [1-4]
- Molecular Formula C10H9NO4
- Molar Weight 207.18 g/mol
- Melting Point 93-98 ℃ and 91 ℃
- Solubility: soluble in EtOH, MeOH, IPA, DCM, acetic acid; non soluble in water
- Color/Form: bright yellow crystals
Structural formula present on Figure 1.
Figure 1. Structure of MDP2NP
Crystalline solid of the MDP2NP can be seen in the picture provided in Figure 2.
Applications of MDP2NP
MDP2NP serves as a key precursor for the synthesis of MDP2P, MDA and MDMA. This nitropropene should be utilized within one week or kept in a cold environment, as it gradually turns to a pale orange color at room temperature over the course of a few weeks, indicating it is beginning to break down.
Chemical Reactions
Reduction of MDP2NP to MDP2P in reaction with electrolytic iron and glacial acetic acid. Figure 3
Figure 3. MDP2P formation from MDP2NP
Reduction to MDA with LAH in anhydrous THF under an inert atmosphere. Figure 4
Figure 4. Reduction to MDA
Full reduction of MDP2NP. Figure 5
Figure 5. Full reduction
Synthesis of MDP2NP [1, 5]
A solution of piperonal in glacial acetic acid was combined with nitroethane, followed by the addition of cyclohexylamine. The mixture was heated on a steam bath for 6 hours, then diluted with water, seeded with a crystal of the product, and left to cool overnight at 10 °C. Bright yellow crystals formed, which were filtered and air-dried to yield 1-(3,4-methylenedioxyphenyl)-2-nitropropene, with a melting point of 93–94 °C. Recrystallization from acetic acid improved the melting point to 97–98 °C. Attempts to synthesize the nitrostyrene using nitroethane in excess as a solvent and anhydrous ammonium acetate as the base resulted in low yields and impure product. Alternatively, successful preparation of the nitrostyrene was achieved by combining the components in cold methanol, using aqueous sodium hydroxide as the base.
MDP2NP synthesis starting from piperonal is shown on Figure 6.
Figure 6. General scheme of MDP2NP synthesis
Conclusion
MDP2NP serves as an important precursor in the synthesis of both MDA (3,4-methylenedioxyamphetamine) and MDMA (3,4-methylenedioxymethamphetamine), which are compounds of significant interest in both pharmacological research and illicit drug production. Due to its molecular structure, MDP2NP is highly reactive and unstable, which poses challenges in its handling and storage. This instability is often attributed to the nitro group present in its structure, making it prone to decomposition under certain conditions. Additionally, the instability of MDP2NP may affect the efficiency of subsequent synthetic steps, necessitating careful optimization of reaction conditions in its preparation.