Sulfisoxazole

Base Information

• Chemical Name: Sulfisoxazole
• CAS No.: 127-69-5
• Deprecated CAS: 207522-06-3
• Molecular Formula: C11H13N3O3S
• Molecular Weight: 267.309
• Hs Code.: 29350030
• European Community (EC) Number: 204-858-9
• NSC Number: 757343,683536,38588,33807,13120
• UNII: 740T4C525W
• DSSTox Substance ID: DTXSID6021292
• Nikkaji Number: J4.409A
• Wikipedia: Sulfafurazole
• Wikidata: Q372598
• NCI Thesaurus Code: C47740
• Pharos Ligand ID: AW9R5XGJLNBD
• Metabolomics Workbench ID: 42659
• ChEMBL ID: CHEMBL453
• Mol file: 127-69-5.mol

Synonyms:Ammonium Salt Sulfisoxazole;Diolamine, Sulfisoxazole;Gantrisin;Gantrisin Pediatric;Monolithium Salt Sulfisoxazole;Monosodium Salt Sulfisoxazole;Neoxazoi;Pediatric, Gantrisin;Sulfadimethyloxazole;Sulfafurazol FNA;Sulfafurazole;Sulfasoxizole;Sulfisoxazole;Sulfisoxazole Diolamine;Sulfisoxazole, Ammonium Salt;Sulfisoxazole, Monolithium Salt;Sulfisoxazole, Monosodium Salt;Sulfisoxazole, Monosodium, Monomesylate Salt;Sulfisoxazole, Triammonium Salt;TL azole;TL-azole;Triammonium Salt Sulfisoxazole;V Sul;V-Sul

Chemical Property of Sulfisoxazole

Chemical Property:

• Appearance/Colour: white to cream powder
• Vapor Pressure: 1.86E-09mmHg at 25°C
• Melting Point: 195 °C
• Refractive Index: 1.626
• Boiling Point: 482.207 °C at 760 mmHg
• PKA: 5.0(at 25℃)
• Flash Point: 245.43 °C
• PSA: 106.60000
• Density: 1.411 g/cm³
• LogP: 3.40940
• Storage Temp.: 2-8°C
• Solubility.: acetone: complete50 mg/ml
• Water Solubility.: <0.1 g/100 mL at 22.5℃
• XLogP3: 1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 267.06776246
• Heavy Atom Count: 18
• Complexity: 374

Purity/Quality:

99% ^*data from raw suppliers

Sulfisoxazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=C(ON=C1C)NS(=O)(=O)C2=CC=C(C=C2)N
• Uses: Sulfisoxazole is a sulfonamide based antibacterial that exhibits activity against wide spectrum of gram-negative and gram-positive bacterium.
• Therapeutic Function: Antibacterial

Technology Process of Sulfisoxazole

There total 16 articles about Sulfisoxazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 69.0%

N-(3,4-dimethylisoxazol-5-yl)-4-nitrobenzenesulfonamide (184644-22-2) → sulfisoxazole (127-69-5)

Guidance literature:

With acetic acid; zinc; In acetonitrile; at 0 - 20 ℃;

DOI:10.1016/j.bmc.2012.06.044

Reference yield:

N4-Acetyl-N1-<3.4-dimethyl-5-isoxazolyl>-sulfanilamid (4206-74-0) → sulfisoxazole (127-69-5)

Guidance literature:

With hydrogenchloride;

Reference yield:

5-amino-3,4-dimethylisoxazol (19947-75-2) → sulfisoxazole (127-69-5)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / 20 °C

2: aq. NaOH / methanol / Heating

With pyridine; sodium hydroxide; In methanol; 1: sulfonylation / 2: Deacetylation;

DOI:10.1016/S0960-894X(00)00366-8

upstream raw materials:

2-methyl-N-sulfanilyl-acetoacetamidine

N-(3,4-dimethylisoxazol-5-yl)-4-nitrobenzenesulfonamide

N⁴-Acetyl-N¹-<3.4-dimethyl-5-isoxazolyl>-sulfanilamid

5-amino-3,4-dimethylisoxazol

Downstream raw materials:

4-((4-(N-(3,4-dimethylisoxazol-5-yl)sulfamoyl)phenyl)amino)-4-oxobutanoic acid

4-(2,6-diamino-pyridin-3-ylazo)-N-(3,4-dimethyl-isoxazol-5-yl)-benzenesulfonamide

4-oxo-4H-chromene-2-carboxylic acid 4-(3,4-dimethyl-isoxazol-5-ylsulfamoyl)-anilide

N-(3,4-dimethyl-isoxazol-5-yl)-4-isothiocyanato-benzenesulfonamide

Refernces

• 1、 Perlovich, German L.,Ryzhakov, Alex M.,Tkachev, Valery V.,Hansen, Lars Kr.,Raevsky, Oleg A.. "Sulfonamide molecular crystals: Structure, sublimation thermodynamic characteristics, molecular packing, hydrogen bonds networks". . p. 4002 - 4016. Retrieved 2013/09/24.
• 2、 Kanda, Yasuhiko,Takahashi, Tadashi,Araki, Yoshitaka,Konoike, Toshiro,Mihara, Shin-ichi,Fujimoto, Masafumi. "Discovery and synthesis of a potent sulfonamide ET(B) selective antagonist". . p. 1875 - 1878. Retrieved 2007/10/03.