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Dapsone

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Identification
Molecular formula
C12H12N2O2S2
CAS number
80-08-0
IUPAC name
3-amino-4-[(2-amino-4-sulfamoyl-phenyl)disulfanyl]benzenesulfonamide
State
State

Dapsone is at room temperature present as a solid substance. It is stable under normal temperatures and pressures.

Melting point (Celsius)
175.00
Melting point (Kelvin)
448.00
Boiling point (Celsius)
385.00
Boiling point (Kelvin)
658.00
General information
Molecular weight
248.31g/mol
Molar mass
248.3090g/mol
Density
1.4797g/cm3
Appearence

Dapsone typically appears as a white crystalline powder. It is practically insoluble in water and freely soluble in chloroform and soluble in dilute mineral acids.

Comment on solubility

Solubility of 3-amino-4-[(2-amino-4-sulfamoyl-phenyl)disulfanyl]benzenesulfonamide

The solubility of 3-amino-4-[(2-amino-4-sulfamoyl-phenyl)disulfanyl]benzenesulfonamide in various solvents is influenced by several chemical properties and structural features. Its complex structure poses interesting challenges and considerations:

  • Polarity: Due to the presence of multiple amino (-NH2) and sulfonamide (-SO2NH2) groups, the compound is anticipated to exhibit significant polarity, enhancing its solubility in polar solvents like water.
  • Hydrophilicity: The sulfonamide and amino groups contribute to its hydrophilic nature, which could promote solubility in aqueous environments, particularly under acidic or neutral pH conditions.
  • Effect of pH: Variations in pH may impact the ionization of the amino and sulfonamide functional groups, thereby affecting overall solubility. It is often observed that increased ionization leads to greater solubility in water.
  • Organic Solvents: While the compound shows promise in water, its solubility in organic solvents (like ethanol or methanol) may be limited due to competitive interactions and molecular size.

In summary, the solubility of 3-amino-4-[(2-amino-4-sulfamoyl-phenyl)disulfanyl]benzenesulfonamide is a complex interplay of its functional groups and their respective interactions with solvents. Understanding these interactions can provide insights into its behavior and utility in various applications.

Interesting facts

Interesting Facts About 3-amino-4-[(2-amino-4-sulfamoyl-phenyl)disulfanyl]benzenesulfonamide

This compound, known for its complex chemical structure, exhibits fascinating characteristics that make it significant in various scientific fields. Here are some engaging facts about 3-amino-4-[(2-amino-4-sulfamoyl-phenyl)disulfanyl]benzenesulfonamide:

  • Pharmaceutical Potential: The presence of sulfonamide groups within its structure indicates potential applications in medicine, particularly in antimicrobial agents. Sulfonamides were among the first antibiotics used in clinical practice.
  • Disulfide Bonds: This compound features a disulfanyl group, which is crucial in biochemistry. Disulfide bonds play critical roles in the stabilization of protein structures, influencing their functionality in biological systems.
  • Amino Groups: The presence of amino groups (–NH2) enhances the compound's nucleophilicity. This can be advantageous in various chemical reactions, including those involving amino acid synthesis and peptide formation.
  • Structure-Activity Relationship: Understanding this compound allows researchers to explore how modifications to its structure can affect biological activity, paving the way for the development of novel therapeutic agents.
  • Research Relevance: Compounds like this one are often subjects of study in fields such as medicinal chemistry and pharmacology, contributing to our understanding of drug mechanisms and interactions.

In summary, 3-amino-4-[(2-amino-4-sulfamoyl-phenyl)disulfanyl]benzenesulfonamide offers a rich field of study for chemists and biochemists alike. As research continues to advance, the insights gained from such compounds could lead to the next generation of effective drugs and treatments in the biomedical arena.

Synonyms
3905-92-8
Metanilamide, 4,4'-dithiodi-
DISULFIDE, BIS(2-AMINO-4-SULFAMOYLPHENYL)
Metanilamide, 4,4'-dithobis-
Metanilamide, 4,4'-dithiobis-
Bis(2-amino-4-sulfonamidophenyl) disulfide
NSC 83217
BRN 2711131
Benzenesulfonamide, 4,4'-dithiobis(3-amino-
DTXSID70192300
4-14-00-02821 (Beilstein Handbook Reference)
DTXCID40114791
Metanilamide, 4,4'-dithiobis-(8CI)
Benzenesulfonamide, 4,4'-dithiobis(3-amino-(9CI)
NSC83217
NSC-83217
4,4'-Dithiobis(3-aminobenzenesulfonamide)
E477AF37KF
4,4'-Dithiobis[3-aminobenzenesulfonamide]
3-amino-4-[(2-amino-4-sulfamoylphenyl)disulfanyl]benzenesulfonamide
Metanilamide,4'-dithiodi-
Metanilamide,4'-dithobis-
Metanilamide,4'-dithiobis-
NCIStruc1_001456
NCIStruc2_001601
UNII-E477AF37KF
4,4'-Disulfanediylbis(3-aminobenzenesulfonamide)
CHEMBL120806
NCI83217
WLN: ZSWOR CZ DSSR BZ DOSZW
CCG-37196
NCGC00013869
NCGC00013869-02
NCGC00096979-01
Benzenesulfonamide,4'-dithiobis[3-amino-
NCI60_041826
3-amino-4-[(2-amino-4-sulfamoyl-phenyl)disulfanyl]benzenesulfonamide