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N-Hydroxysuccinimide ester of salicylic acid

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Identification
Molecular formula
C11H7NO5
CAS number
98444-31-4
IUPAC name
4-(2,5-dioxopyrrol-1-yl)-2-hydroxy-benzoic acid
State
State

The compound is a solid at room temperature.

Melting point (Celsius)
146.00
Melting point (Kelvin)
419.20
Boiling point (Celsius)
365.40
Boiling point (Kelvin)
638.50
General information
Molecular weight
235.18g/mol
Molar mass
235.1970g/mol
Density
1.4620g/cm3
Appearence

The compound is typically found as a white to off-white crystalline powder. It is slightly soluble in water but dissolves more readily in organic solvents.

Comment on solubility

Solubility of 4-(2,5-dioxopyrrol-1-yl)-2-hydroxy-benzoic acid

The solubility of 4-(2,5-dioxopyrrol-1-yl)-2-hydroxy-benzoic acid (C11H7NO5) is influenced by its molecular structure, which contains both hydrophobic and hydrophilic regions. This compound exhibits interesting solubility behavior, which can be summarized as follows:

  • Polar Functional Groups: The presence of hydroxyl (-OH) and carboxylic acid (-COOH) functional groups enhances solubility in polar solvents such as water due to hydrogen bonding.
  • Hydrophobic Character: The aromatic ring adds a degree of hydrophobicity, which may limit solubility in highly polar solvents, but can dissolve better in organic solvents.
  • pH Dependency: The solubility can vary with pH levels. At low pH, the carboxylic acid can remain protonated, whereas at higher pH, deprotonation occurs, potentially increasing solubility.
  • Temperature Effects: Increasing temperature can enhance solubility, as higher temperatures generally promote solute-solvent interactions.

In summary, this compound shows a unique interplay of solubility characteristics. It is quoted that "the intricate balance of hydrophilic and hydrophobic elements defines the solubility landscape of complex organic compounds." Understanding these factors is crucial for applications such as drug formulation and material science, where solubility impacts efficacy and performance.

Interesting facts

Interesting Facts about 4-(2,5-dioxopyrrol-1-yl)-2-hydroxy-benzoic acid

4-(2,5-dioxopyrrol-1-yl)-2-hydroxy-benzoic acid, commonly known by its chemical structure, presents a fascinating area of study in organic and medicinal chemistry. Here are some intriguing aspects of this compound:

  • Pharmacological Potential: This compound belongs to a class of derivatives that show promise in pharmaceutical applications due to potential anti-inflammatory and analgesic properties.
  • Functional Groups: It contains multiple functional groups including a carboxylic acid and a hydroxyl group, which can play a crucial role in hydrogen bonding, enhancing its solubility and reactivity in various chemical environments.
  • Biological Relevance: The presence of a pyrrolidine ring combined with a benzoic acid moiety could suggest its utility as a ligand in biological systems, possibly interacting with proteins or enzymes.
  • Synthetic Versatility: This compound can be synthesized through various organic reactions, making it a versatile building block for creating more complex molecules within medicinal chemistry.
  • Research Interest: Given its unique structure, it has caught the attention of researchers exploring new drug candidates, particularly in the fields of oncology and neurology, where complex organic molecules are often required.

As a chemistry student, it is crucial to appreciate how such compounds are not merely a combination of atoms but rather structures with potential. Studying compounds like 4-(2,5-dioxopyrrol-1-yl)-2-hydroxy-benzoic acid encourages critical thinking in synthesis and application aspects of organic chemistry.

In the words of renowned chemists, understanding these compounds leads us “one step closer to unlocking the mysteries of molecular interactions and the potential they hold for therapeutic advancements.” The study of this compound encapsulates the beauty and complexity of chemical research!

Synonyms
19232-43-0
N-(4-Carboxy-3-hydroxyphenyl)maleimide
4-Maleimidylsalicylic acid
4-MALEIMIDOSALICYLIC ACID
4-(2,5-dioxopyrrol-1-yl)-2-hydroxybenzoic acid
4-(2,5-dioxo-2,5-dihydro-1h-pyrrol-1-yl)-2-hydroxybenzoic acid
NSC 59375
H822IOP4G8
Benzoic acid, 4-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)-2-hydroxy-
NSC-59375
UNII-H822IOP4G8
DTXSID30172820
SALICYLIC ACID, 4-MALEIMIDO-
4-(2,5-DIHYDRO-2,5-DIOXO-1H-PYRROL-1-YL)-2-HYDROXYBENZOIC ACID
NSC59375
M 84
CHEMBL509675
SCHEMBL3050771
DTXCID7095311
AKOS000139989
N-(4-Carboxy-3-hydroxy)phenylmaleimide
AS-71998
DB-015394
HY-115756
CS-0255408
D95892
4-(2,5-dioxopyrrol-1-yl)-2-hydroxy-benzoic acid