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Amiodarone

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Identification
Molecular formula
C19H15I3NO4
CAS number
1951-25-3
IUPAC name
4-(4-acetoxy-3-iodo-phenoxy)-3,5-diiodo-benzoic acid
State
State
Amiodarone in its pure form is a solid at room temperature, often formulated into tablets for pharmaceutical use.
Melting point (Celsius)
172.00
Melting point (Kelvin)
445.15
Boiling point (Celsius)
0.00
Boiling point (Kelvin)
0.00
General information
Molecular weight
645.16g/mol
Molar mass
645.1550g/mol
Density
2.5900g/cm3
Appearence

Amiodarone hydrochloride typically appears as a white crystalline powder. It is slightly soluble in water and freely soluble in alcohol and chloroform, which aligns with its manufacturing requirements and pharmaceutical applications. The compound itself without the hydrochloride salt also has a similar appearance but is less commonly handled outside of its salt form due to solubility and pharmaceutical formulation reasons.

Comment on solubility

Solubility of 4-(4-acetoxy-3-iodo-phenoxy)-3,5-diiodo-benzoic acid

The solubility of 4-(4-acetoxy-3-iodo-phenoxy)-3,5-diiodo-benzoic acid is a complex topic influenced by several structural characteristics and environmental conditions. Acids, particularly those with multiple halogen substituents like this compound, usually exhibit unique solubility behaviors due to their capacity to engage in hydrogen bonding and ionization.

Factors Influencing Solubility:

  • Polarity: The presence of multiple iodine atoms can increase the compound's polarity, potentially enhancing its solubility in polar solvents.
  • Hydrogen Bonding: The carboxylic acid group (-COOH) can participate in hydrogen bonding, which can facilitate solubility in alcohols and other hydrophilic solvents.
  • Temperature: As with many organic compounds, solubility can be temperature-dependent; higher temperatures might lead to increased solubility.
  • pH Levels: The acidic nature of the carboxylic group allows for improved solubility in basic conditions (higher pH) due to deprotonation.

While 4-(4-acetoxy-3-iodo-phenoxy)-3,5-diiodo-benzoic acid may exhibit limited solubility in nonpolar solvents, it is likely to dissolve better in polar organic solvents and slightly alkaline conditions. Furthermore, potential interactions with solvation shells in aqueous environments could also modify its solubility profile.

As a result, it is crucial to conduct solubility tests under various conditions to fully understand the solubility characteristics of this compound.

Interesting facts

Interesting Facts about 4-(4-acetoxy-3-iodo-phenoxy)-3,5-diiodo-benzoic acid

4-(4-acetoxy-3-iodo-phenoxy)-3,5-diiodo-benzoic acid, often abbreviated in scientific discussions, is a fascinating compound that plays a crucial role in various fields of research and application. Here are some notable highlights:

  • Structure and Functionality: This compound is characterized by its intricate aromatic structure which includes multiple iodine atoms. The presence of iodine not only enhances its organic, as well as medicinal properties, but also serves to make it an effective agent in nuclear medicinal imaging.
  • Pharmaceutical Relevance: Research has indicated that compounds containing iodine, such as this one, exhibit potential therapeutic properties. They are often investigated for applications in the treatment of diseases, especially related to thyroid function.
  • Acetoxy Group Impact: The acetoxy functional group contributes to the compound's solubility in various organic solvents and allows for modifications that can enhance its reactivity, making it a significant target for a variety of chemical reactions.
  • Environmental Considerations: Like many halogenated compounds, the environmental impact of using iodine in chemical synthesis is a topic of concern. Thus, the synthesis processes strive for sustainable methods to mitigate any adverse effects.
  • Research Applications: This compound has been explored in the fields of drug development and materials science, making it a subject of interest for chemists aiming to innovate in areas like targeting delivery systems and diagnostic agents.

As a compound rich in iodine and functional groups, **4-(4-acetoxy-3-iodo-phenoxy)-3,5-diiodo-benzoic acid** presents ample opportunities for study and application. Its multifaceted nature underscores the importance of iodine in enhancing both the utility and performance of chemical compounds in various scientific endeavors.

In summary, this compound embodies the exciting intersection of chemistry and application, inspiring future explorations that could lead to impactful findings in medicinal and environmental chemistry.

Synonyms
Acetiromate
2260-08-4
Acetiromate [INN]
Acetiromato
4-(4-acetyloxy-3-iodophenoxy)-3,5-diiodobenzoic acid
8Q5153W1NW
4-(4-Hydroxy-3-iodophenoxy)-3,5-diiodobenzoic acid acetate
Adecol
4-(4-acetoxy-3-iodophenoxy)-3,5-diiodobenzoic acid
Acetiromatum [INN-Latin]
Acetiromato [INN-Spanish]
Acetiromatum
TBF 43
Acetyltriiodothyronine formic acid
3,5-Diiodo-4-(4'-acetoxy-3'-iodophenoxy)benzoic acid
ACETIROMATE [MART.]
4-(4-Acetoxy-3-iodphenoxy)-3,5-diodbenzoesaeure
UNII-8Q5153W1NW
3,5-Diiodo-4-(3-iodo-4-acetoxyphenoxy)benzoic acid
3,5-Diiodo-4-(4-acetoxy-3-iodophenoxy)benzoic acid
SCHEMBL2110761
CHEMBL2105921
DTXSID60177121
AXVCIZJRCOHMQX-UHFFFAOYSA-N
Benzoic acid, 4-(4-(acetyloxy)-3-iodophenoxy)-3,5-diiodo-
Benzoic acid, 4-(4-hydroxy-3-iodophenoxy)-3,5-diiodo-, acetate
AKOS040745464
BENZOIC ACID, 3,5-DIIODO-4-(4-HYDROXY-3-IODOPHENOXY)-, ACETATE
DA-70494
HY-119858
CS-0078168
NS00120281
Q15408429