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Sulfamethanilide

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Identification
Molecular formula
C12H12N2O2S
CAS number
633-03-4
IUPAC name
4-amino-N-phenyl-benzenesulfonamide
State
State

At room temperature, Sulfamethanilide is typically in a solid state. It does not readily dissolve in water, making it suitable for applications where a solid form is necessary.

Melting point (Celsius)
150.00
Melting point (Kelvin)
423.15
Boiling point (Celsius)
734.50
Boiling point (Kelvin)
1 007.65
General information
Molecular weight
233.30g/mol
Molar mass
233.2870g/mol
Density
1.3950g/cm3
Appearence

Sulfamethanilide typically appears as an off-white to beige solid. It may be in the form of crystalline powder, which can vary slightly in color due to the presence of impurities or as a characteristic of the compound itself.

Comment on solubility

Solubility of 4-amino-N-phenyl-benzenesulfonamide

The solubility of 4-amino-N-phenyl-benzenesulfonamide, also known as sulfanilamide, can be characterized as follows:

  • Water Solubility: 4-amino-N-phenyl-benzenesulfonamide has moderate solubility in water, primarily due to the presence of the sulfonamide group which tends to increase polarity.
  • Solvent Variation: Its solubility can be influenced by pH levels; for instance, it is more soluble in alkaline conditions compared to neutral or acidic environments.
  • Temperature Effects: Increased temperature usually results in improved solubility, which is a common phenomenon observed in many solid compounds.
  • Solvent Specificity: In non-polar solvents, solubility is significantly lower due to the hydrocarbon nature of the phenyl groups.

It’s important to note that the solubility characteristics can vary between different formulations and environmental conditions. Understanding these aspects is crucial for applications in pharmaceuticals and chemical processes.

In summary, the solubility profile of 4-amino-N-phenyl-benzenesulfonamide can be encapsulated in the phrase: "A balance of polarity and environmental conditions dictates its dissolving prowess."

Interesting facts

Exploring 4-amino-N-phenyl-benzenesulfonamide

4-amino-N-phenyl-benzenesulfonamide, commonly known as a sulfanilamide derivative, is an intriguing compound in the field of medicinal chemistry. Its significance primarily lies in its historical application and its role in the development of antibiotic therapies. Here are some fascinating facts about this compound:

  • Antibiotic Properties: This compound played a crucial role as one of the first sulfonamide antibiotics, which revolutionized the treatment of bacterial infections in the early 20th century.
  • Structure-Activity Relationship: The sulfonamide group is key to its antibacterial activity, providing insights into how modifications to the structure can enhance its pharmacological properties.
  • Mechanism of Action: 4-amino-N-phenyl-benzenesulfonamide functions by inhibiting the bacterial enzyme dihydropteroate synthase, crucial in the synthesis of folate, effectively stifling bacterial growth.
  • Historical Significance: The introduction of sulfanilamide marked the beginning of the modern antibiotic era, paving the way for the use of antibiotics and transforming medical practices.
  • Continued Research: Nowadays, researchers are investigating its derivatives and analogs to improve efficacy and decrease resistance in bacteria, emphasizing the compound's ongoing relevance.

The legacy of 4-amino-N-phenyl-benzenesulfonamide in medicine cannot be overstated, as it embodies a significant milestone in the fight against infectious diseases. As noted by researchers, *"Sulfonamides inspired a new class of synthetic antibiotics that remains relevant in treating infections."* This compound serves as a classic example of how a single chemical entity can lead to widespread advancements in healthcare.

Ultimately, 4-amino-N-phenyl-benzenesulfonamide not only illustrates the importance of synthetic chemistry in drug development but also highlights the ongoing need for innovative approaches to tackle emerging bacterial resistance.

Synonyms
4-Amino-N-phenylbenzenesulfonamide
Sulfabenz
127-77-5
Benzenesulfonamide, 4-amino-N-phenyl-
SULFANILANILIDE
Sulfabenzo
Eastman-4770
Sulfa Vet
Sulfabenzum
Solfabenzo
p-Aminobenzenesulfonanilide
4-Aminobenzenesulfonanilide
Solfabenzo [DCIT]
N(sup1)-Phenylsulfanilamide
NSC-2619
Sulfabenz [USAN:INN]
p-Amino-N-phenylbenzenesulfonamide
Sulfabenzum [INN-Latin]
Sulfabenzo [INN-Spanish]
DTXSID9046287
2Y70F6K03F
SULFABENZ [INN]
NSC 2619
SULFABENZ [MI]
SULFABENZ [USAN]
EINECS 204-865-7
DTXCID7026287
Sulfabenzum (INN-Latin)
Sulfabenzo (INN-Spanish)
Sulfanilanilide (8CI)
RefChem:889489
204-865-7
4-Amino-N-phenyl-benzenesulfonamide
MFCD00233654
4-amino-N-phenylbenzene-1-sulfonamide
NSC2619
[(4-aminophenyl)sulfonyl]phenylamine
NCGC00160668-01
CAS-127-77-5
UNII-2Y70F6K03F
Sulfanilsaure-anilid
component of Sulfa Vet
Sulfabenz (USAN/INN)
MLS004754478
SCHEMBL193566
CHEMBL359839
SCHEMBL2152296
SCHEMBL10528966
SCHEMBL10528973
SCHEMBL10774342
SCHEMBL11712569
HMS1757M22
4-amino-N-phenylbenzenesulphonamide
ALBB-000048
Tox21_111972
BBL014308
SBB000878
STK122969
AKOS000117120
Tox21_111972_1
NCGC00160668-03
BP-21243
SMR000150219
ST039496
SY131879
VS-04262
CS-0186941
NS00024049
EN300-06306
4-Amino-N-phenylbenzenesulfonamide, AldrichCPR
D05945
D83866
127A775
F211956
Q27255797
Z56923284
VVM