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Nitrofurantoin

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Identification
Molecular formula
C8H6N4O5
CAS number
67-20-9
IUPAC name
2-(diethylamino)ethyl 3-methyl-5-(5-nitro-2-furyl)isoxazole-4-carboxylate
State
State

Nitrofurantoin is a solid at room temperature.

Melting point (Celsius)
272.00
Melting point (Kelvin)
545.15
Boiling point (Celsius)
0.00
Boiling point (Kelvin)
0.00
General information
Molecular weight
238.21g/mol
Molar mass
238.2080g/mol
Density
1.6352g/cm3
Appearence

Nitrofurantoin appears as a yellow, crystalline, and slightly bitter compound.

Comment on solubility

Solubility of 2-(diethylamino)ethyl 3-methyl-5-(5-nitro-2-furyl)isoxazole-4-carboxylate

The solubility of 2-(diethylamino)ethyl 3-methyl-5-(5-nitro-2-furyl)isoxazole-4-carboxylate can be influenced by several factors due to its complex structure. Here are some essential points to consider:

  • Polarity: The presence of a diethylamino group increases the overall polarity of the compound, potentially enhancing its solubility in polar solvents such as water and alcohols.
  • Functional groups: The carboxylate group is known for its ability to form hydrogen bonds, which may contribute to its solubility in aqueous solutions.
  • Hydrophobic interactions: The isoxazole ring and the nitro-furyl moiety serve as hydrophobic regions, which might limit solubility in polar solvents while increasing it in organic solvents.
  • pH dependence: The solubility of the compound may vary significantly with changes in pH, as the ionization of the carboxyl group can affect solubility characteristics.

In conclusion, the solubility of 2-(diethylamino)ethyl 3-methyl-5-(5-nitro-2-furyl)isoxazole-4-carboxylate is primarily dictated by a balance between its polar and non-polar attributes. Understanding these aspects can provide valuable insights into the compound's behavior in various environments.

Interesting facts

Interesting Facts about 2-(Diethylamino)ethyl 3-methyl-5-(5-nitro-2-furyl)isoxazole-4-carboxylate

The compound 2-(diethylamino)ethyl 3-methyl-5-(5-nitro-2-furyl)isoxazole-4-carboxylate belongs to a class of organic compounds that exhibit intriguing biological properties.

Biological Significance

This compound has been studied extensively for its potential as a pharmaceutical agent. Some of its noteworthy characteristics include:

  • Antimicrobial Activity: Research suggests that the compound may possess significant antimicrobial properties, making it a candidate for developing new medications.
  • Antitumor Effects: Preliminary studies indicate that it may show efficacy against certain types of tumors, contributing to ongoing cancer research.
  • Neuropharmacological Potential: Due to the presence of a diethylamino group, it might influence the central nervous system, presenting possibilities for treating neurological disorders.

Synthesis and Applications

The synthetic pathways for this compound are often complex, involving multiple steps to achieve its unique structure. Some key points include:

  • Multistep Synthesis: The synthesis typically requires various reagents and conditions, reflecting the sophistication of modern organic synthesis.
  • Industrial Relevance: Beyond its potential therapeutic applications, the compound may also play a role in agricultural chemistry, particularly as a pesticide or herbicide due to its structural features.

Future Research Directions

Ongoing research is likely to focus on:

  • Mechanistic Studies: Understanding how this compound interacts with biological systems at the molecular level.
  • Structure-Activity Relationship (SAR) Investigations: Exploring the relationships between its chemical structure and biological activity, which could inform the design of more effective derivatives.
  • Potential Toxicity Assessments: Determining safe usage levels and understanding any side effects that may accompany its use.

In summary, 2-(diethylamino)ethyl 3-methyl-5-(5-nitro-2-furyl)isoxazole-4-carboxylate represents a fascinating intersection of organic chemistry and pharmacology, with prospects that could significantly impact both medicine and agriculture.

Synonyms
4-Isoxazolecarboxylic acid, 3-methyl-5-(5-nitro-2-furyl)-, 2-(diethylamino)ethyl ester
22997-00-8
3-Methyl-5-(5-nitro-2-furyl)-4-isoxazolecarboxylic acid 2-(diethylamino)ethyl ester
DTXSID00177549