Basic information
- CAS
103-12-8- Standard SMILES
Nc1ccc(N=Nc2ccc(S(N)(=O)=O)cc2)c(N)c1- InChIKey
ABBQGOCHXSPKHJ-UHFFFAOYSA-N- Molecular formula
- C12H13N5O2S
- Average molar mass
- 291.33 g/mol
- Monoisotopic mass
- 291.07899585
Overview
Prontosil is a diphenyldiazene compound having two amino substituents at the 2- and 4-positions and an aminosulphonyl substituent at the 4'-position. It was the first antibacterial drug, (introduced 1935) and the first of the sulfonamide antibiotics. It has a role as an antimicrobial agent and an antibacterial drug. It is a member of azobenzenes and a sulfonamide. It is functionally related to a sulfanilamide.
Names & identifiers
- Preferred name
- 4-((2,4-Diaminophenyl)diazenyl)benzene-1-sulfonamide
- IUPAC
- 4-[(2,4-diaminophenyl)diazenyl]benzenesulfonamide
- English name
- p-[(2,4-diaminophenyl)azo]benzenesulphonamide
- Molecular formula
- C12H13N5O2S
- Molecular weight
- 291.33
Names & synonyms
DTXSID708715874-((2,4-Diaminophenyl)diazenyl)benzene-1-sulfonamide4-[(2,4-Diaminophenyl)diazenyl]benzene-1-sulfonamideRefChem:1069632DTXCID30819243prontosilSulfamidochrysoidine103-12-8Prontosil rubrumRubiazol4-[(2,4-diaminophenyl)diazenyl]benzenesulfonamideQ64Q9N6Q6O
Show more names
ParazolRelbazonRubiazol IPronzin rubrumProntosil flavum4-(2,4-diaminophenyl)azobenzenesulfonamidep-[(2,4-Diaminophenyl)azo]benzenesulfonamide
p-((2,4-Diaminophenyl)azo)benzenesulphonamideP-[(2,4-diaminophenyl)azo]benzenesulphonamideRelbazon; Streptocide; Sulfamidochrysoidinprontosil redUNII-Q64Q9N6Q6OEINECS 203-081-2Aseptil rojo (TN)AI3-09088
Database identifiers
- CAS
103-12-8- PubChem CID
- 66895
- DTXSID
Properties
Computed structural properties
- XLogP
- 0.9
- Topological polar surface area
- 145 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 3
- Heavy atoms
- 20
- Formal charge
- 0
- Complexity
- 439
Experimental & physicochemical properties
DrugsPharmaceuticals -> Antibiotics
Physicochemical properties
- Melting point
- 249.5 °C · 249.5°C
- Density
- 1.4999 · 1.4999 (rough estimate)
- refractive index
- 1.563 · 1.5630 (estimate)
- Boiling point
- 601.2 · 601.2±65.0 °C(Predicted)
- pka
- 9.73 · 9.73±0.10(Predicted)
- FDA UNII
- 64 Q9N6Q6O · Q64Q9N6Q6O
Chemistry & industry
Suppliers2 total
BOC Sciences16314854226; +8616314854226 · [email protected]
Dideu Industries Group Limited+86-29-81148696 +86-15129568250 · [email protected]
Additional notes
DefinitionChEBI: A diphenyldiazene compound having two amino substituents at the 2- and 4-positions and an aminosulphonyl substituent at the 4'-position. It was the first antibacterial drug, (introduced 1935) and the first of the sulfonamide antibiotics.
Related reactions
0 records
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Compound notes
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