Sulfanilamide

Base Information

• Chemical Name: Sulfanilamide
• CAS No.: 63-74-1
• Deprecated CAS: 102489-34-9,12765-80-9,1337-36-6,1337-39-9,24706-25-0,12765-80-9,1337-36-6,1337-39-9,24706-25-0
• Molecular Formula: C6H8N2O2S
• Molecular Weight: 172.208
• Hs Code.: 2935.00
• European Community (EC) Number: 200-563-4
• NSC Number: 757404,7618
• UN Number: 1759
• UNII: 21240MF57M
• DSSTox Substance ID: DTXSID4023622
• Nikkaji Number: J4.829A
• Wikipedia: Sulfanilamide
• Wikidata: Q423423
• NCI Thesaurus Code: C47738
• Pharos Ligand ID: YJUV95M8L1KL
• Metabolomics Workbench ID: 42656
• ChEMBL ID: CHEMBL21
• Mol file: 63-74-1.mol

Synonyms:4 aminobenzenesulfonamide;4-aminobenzenesulfonamide;Azol Polvo;sulfanilamide;sulfanilamide barium salt;sulfanilamide cadmium salt;sulfanilamide hydrochloride;sulfanilamide lithium salt;sulfanilamide magnesium salt;sulfanilamide monohydrate;sulfanilamide silver salt;Sulfanilamide Sodium;sulfanilamide sodium salt;sulfanilamide strontium salt;sulfanilamide zinc salt;Sulphanilamide

Chemical Property of Sulfanilamide

Chemical Property:

• Appearance/Colour: White to almost white crystalline powder
• Vapor Pressure: 0.00001 hPa (70 °C)
• Melting Point: 164-167 °C
• Refractive Index: 1.6490 (estimate)
• Boiling Point: 400.5 °C at 760 mmHg
• PKA: pKa 10.65(H2O t = 25.0±0.5 I = 0.2) (Uncertain)
• Flash Point: 196 °C
• PSA: 94.56000
• Density: 1.427 g/cm³
• LogP: 2.27850
• Storage Temp.: 0-6°C
• Solubility.: 5.37g/l
• Water Solubility.: 7.5 g/L at 25 ºC
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 172.03064868
• Heavy Atom Count: 11
• Complexity: 211
• Transport DOT Label: Corrosive

Purity/Quality:

99%min ^*data from raw suppliers

Sulphanilamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 40
• Safety Statements: 24/25-36-22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Uses -> Pharmaceuticals
• Canonical SMILES: C1=CC(=CC=C1N)S(=O)(=O)N
• Uses: Sulfanilamide is the main raw material for the synthesis of sulfa drugs. Used as a reagent to determine nitrite, also used in the pharmaceutical industry. Used as intermediates for the synthesis of other sulfa drugs, even for wound disinfection. Amino benzene sulfonamide is intermediate of herbicide asulam, as well as intermediate of sulfa medicine. Veterinary medicine, topical anti-inflammatory drugs, for analysis and detection. Wide spectrum antibacterial, having antibacterial effects on hemolytic streptococcus, Neisseria meningitidis, Staphylococcus aureus and other Gram-positive and negative bacteria. This product is topical application, it can be partially absorbed from the wound. For trauma infections of hemolytic streptococcus and staphylococcus. It can also be used to quickly stop the bleeding wound. Sulfonamide antibacterial Sulfanilamide is an antibacterial and used in the treatment of vaginal yeast infections. It is a competitive inhibitor of dihydropteroate synthestase to block the synthesis of folic acid. It serves as an intermediate for the preparation of 2,6-disubstituted anilines by electrophilic substitution followed by removal of the sulfonamide blocking group by desulfonation with sulfuric acid. Sulfanilamide is an antibacterial agent and antimicrobial agent of sulfonamide type (topical and vaginal).
• Description: Sulfanilamide is an organic sulfur compound structurally similar to p-aminobenzoic acid (PABA) with antibacterial property. Sulfanilamide competes with PABA for the bacterial enzyme dihydropteroate synthase, thereby preventing the incorporation of PABA into dihydrofolic acid, the immediate precursor of folic acid. This leads to an inhibition of bacterial folic acid synthesis and de novo synthesis of purines and pyrimidines, ultimately resulting in cell growth arrest and cell death.

Technology Process of Sulfanilamide

There total 71 articles about Sulfanilamide 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: 99.0%

p-nitrobenzenesulfonamide (6325-93-5) → sulfanilamide (63-74-1)

Guidance literature:

With hydrogen; In methanol; ethyl acetate; for 4h; under 760.051 Torr; Heating; Flow reactor; Green chemistry;

DOI:10.1002/cctc.201402488

Reference yield: 99.0%

4-azidobenzenesulfonamide (36326-86-0) → sulfanilamide (63-74-1)

Guidance literature:

With D-glucose; potassium hydroxide; In water; at 85 ℃; for 0.0833333h; chemoselective reaction; Green chemistry;

DOI:10.1039/c7gc01593c

Reference yield: 98.3%

p-acetylaminobenzenesulfonamide (121-61-9) → sulfanilamide (63-74-1)

Guidance literature:

With water; acetic acid; sodium hydroxide; at 65 ℃; for 6h; pH=6-8; Reagent/catalyst; Temperature;

upstream raw materials:

4-Chlorobenzenesulfonamide

p-nitrobenzenesulfonamide

N-formyl-sulfanilyl chloride

4,4'-(carbonylbis(azanediyl))dibenzenesulfonamide

Downstream raw materials:

N-[2-bromo-3ξ-(5-nitro-[2]thienyl)-allylidene]-sulfanilic acid amide

N-[2-bromo-3ξ-(5-nitro-[2]thienyl)-allylidene]-sulfanilic acid acetylamide

N-(pyridine-2-thiocarbonyl)-sulfanilic acid-(pyridine-2-thiocarbonylamide)

4-amino-N-pyridin-3-yl-benzenesulfonamide

Refernces

• 1、 Krishnan, Saravanan,Patel, Paresh N.,Balasubramanian, Kalpattu K.,Chadha, Anju. "Yeast supported gold nanoparticles: an efficient catalyst for the synthesis of commercially important aryl amines". supporting information. p. 1915 - 1923. Retrieved 2021/02/06.
• 2、 -. "Green process synthesis method of sulfanilamide". Paragraph 0019. . Retrieved 2021/09/04.