Sulfamethazine

Base Information

• Chemical Name: Sulfamethazine
• CAS No.: 57-68-1
• Molecular Formula: C12H14N4O2S
• Molecular Weight: 278.335
• Hs Code.: 29350090
• European Community (EC) Number: 200-346-4
• NSC Number: 757326,683529,67457
• UNII: 48U51W007F
• DSSTox Substance ID: DTXSID6021290
• Nikkaji Number: J106.516E
• Wikipedia: Sulfadimidine
• Wikidata: Q3976823
• NCI Thesaurus Code: C61960
• Metabolomics Workbench ID: 43576
• ChEMBL ID: CHEMBL446
• Mol file: 57-68-1.mol

Synonyms:Benzenesulfonamide, 4-amino-N-(4,6-dimethyl-2-pyrimidinyl)-;Sulfadimezine;Sulfadimidine;Sulfamethazine;sulphamethazine;Sulphamezathine

Chemical Property of Sulfamethazine

Chemical Property:

• Appearance/Colour: White to off-solid
• Melting Point: 197 °C
• Refractive Index: 1.6440 (estimate)
• Boiling Point: 526.2 °C at 760 mmHg
• PKA: 7.4, 2.65(at 25℃)
• Flash Point: 272.1 °C
• PSA: 106.35000
• Density: 1.392 g/cm³
• LogP: 3.21140
• Storage Temp.: 2-8°C
• Solubility.: acetone: soluble50mg/mL
• Water Solubility.: 150mg/100mL (29 ºC)
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 278.08374688
• Heavy Atom Count: 19
• Complexity: 377

Purity/Quality:

99% ^*data from raw suppliers

Sulfadimidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 23-24/25-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=NC(=N1)NS(=O)(=O)C2=CC=C(C=C2)N)C
• Description: Sulfamethazine is an antibacterial sulfonamide. Like other sulfonamides, sulfamethazine is bacteriostatic, competitively inhibiting dihydropteroate synthase to block folate synthesis and inhibit growth and multiplication. Sulfamethazine is metabolized by cytochrome P450 isoforms and arylamine N-acetyltransferase 2 in a sex-dependent manner.
• Uses: Antibacterial Sulfamethazine is an antibacterial.This compound is a contaminant of emerging concern (CECs).
• Therapeutic Function: Antimicrobial

Technology Process of Sulfamethazine

There total 17 articles about Sulfamethazine 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:

N-[4-(4,6-Dimethyl-pyrimidin-2-ylsulfamoyl)-phenyl]-acetamide (100-90-3) → sulfadimesine (57-68-1)

Guidance literature:

With sodium hydroxide;

DOI:10.1021/ja01853a045

Reference yield:

2-Amino-4,6-dimethylpyrimidine (767-15-7,184433-59-8) → sulfadimesine (57-68-1)

Guidance literature:

Multi-step reaction with 2 steps

2: iron-powder; aq.-ethanolic HCl

With hydrogenchloride; iron;

DOI:10.1021/jo01180a011

Reference yield:

p-acetylaminobenzenesulfonyl chloride (121-60-8) → sulfadimesine (57-68-1)

Guidance literature:

Multi-step reaction with 2 steps

2: aq. NaOH solution

With sodium hydroxide;

DOI:10.1021/ja01853a045

upstream raw materials:

2-chloro-4,6-dimethylpyrimidine

sulfanilamide

(E)-4-(piperidino)pent-3-en-2-one

1-amino-4-({[amino(imino)methyl]amino}sulfonyl)benzene

Downstream raw materials:

N-(4,6-dimethyl-pyrimidin-2-yl)-4-[(4-oxo-2-thioxo-thiazolidin-5-ylidene)-hydrazino]-benzenesulfonamide

4-[(1H-benzimidazol-2-ylmethyl)-amino]-N-(4,6-dimethylpyrimidin-2-yl)-benzenesulfonamide

4-(2-Amino-4-phenyl-thiazol-5-ylazo)-N-(4,6-dimethyl-pyrimidin-2-yl)benzene sulfonamide

4-(7-Chloro-5,8-dioxo-5,8-dihydro-quinolin-6-ylamino)-N-(4,6-dimethyl-pyrimidin-2-yl)-benzenesulfonamide

Refernces

• 1、 -. "Process for formulating a synthetic drug for use in animal feed, and resulting formulation". . . Retrieved 2008/06/13.