2-(4-Methoxybenzyl)isothiazolidine 1,1-dioxide

Base Information

• Chemical Name: 2-(4-Methoxybenzyl)isothiazolidine 1,1-dioxide
• CAS No.: 158089-76-0
• Molecular Formula: C11H15NO3S
• Molecular Weight: 241.30700
• Hs Code.: 2934100090
• DSSTox Substance ID: DTXSID20443152
• Nikkaji Number: J2.287.433K
• Wikidata: Q82260864
• Mol file: 158089-76-0.mol

Synonyms:158089-76-0;2-(4-Methoxybenzyl)isothiazolidine 1,1-dioxide;N-(4-Methoxybenzyl)-1,3-propanesultam;2-[(4-methoxyphenyl)methyl]-1,2-thiazolidine 1,1-dioxide;Isothiazolidine, 2-[(4-methoxyphenyl)methyl]-, 1,1-dioxide;2-(4-Methoxybenzyl)isothiazolidine1,1-dioxide;SCHEMBL20498009;DTXSID20443152;MFCD09972135;AKOS015888888;BS-21583;CS-0207809;2-[(4-methoxyphenyl)methyl]-1,2-thiazolidine-1,1-dione;2-[(4-METHOXYPHENYL)METHYL]-1??,2-THIAZOLIDINE-1,1-DIONE;2-[(4-Methoxyphenyl)methyl]-1lambda~6~,2-thiazolidine-1,1-dione;N-(4-Methoxybenzyl)-1,3-propanesultam 100 microg/mL in Acetonitrile

Chemical Property of 2-(4-Methoxybenzyl)isothiazolidine 1,1-dioxide

Chemical Property:

• Melting Point: >47°C (dec.)
• Boiling Point: 397.0±44.0 °C(Predicted)
• PKA: -4.81±0.20(Predicted)
• PSA: 54.99000
• Density: 1.279±0.06 g/cm3(Predicted)
• LogP: 2.24940
• Storage Temp.: 2-8°C
• Solubility.: Acetonitrile (Slightly), Chloroform (Slightly)
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 241.07726451
• Heavy Atom Count: 16
• Complexity: 315

Purity/Quality:

98.5% ^*data from raw suppliers

2-(4-Methoxybenzyl)isothiazolidine1,1-Dioxide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)CN2CCCS2(=O)=O
• Description: The antibacterial properties of the sulfonamides were discovered in the mid-1930s following an incorrect hypothesis but after observing the results carefully and drawing correct conclusions. Prontosil rubrum, a red dye, was one of a series of dyes examined by Gerhard Domagk of Bayer of Germany in the belief that it might be taken up selectively by certain pathogenic bacteria and not by human cells, in a manner analogous to the way in which the Gram stain works, and, therefore, serve as a selective poison to kill these cells. The dye, indeed, proved to be active in vivo against streptococcal infections in mice. Curiously, it was not active in vitro.
• Uses: Sulfanilamide drugs do not currently have a clear classification. However, they are grouped as systemic (absorptive action), and local. They are subdivided into short-lasting (sulfacytine, sulfadiazin, sulfamerazine, sulfametazine, sulfametizole, sulfisoxazole); moderate-lasting (sulfamethoxazole, sulfapyridine); and long-lasting (sulfamethoxypiridazine, sulfamter), which, however, are no longer used as independent drugs because of extremely rare, yet nonetheless occurring, hypersensitivity reactions. Drugs for local use include those for ophthalmological use (sulfacetamide, sulfozoxazol); vaginal use (sulfabenzamide, sulfacetamide, sulfathiazole, sulfizoxazol); and external use (maphenid, silver sulfadiazine). Finally, this group includes sulfasalazine and phthalylsulfathiazole, a drug that acts in the lumen of the intestines, but which is poorly absorbed from the gastrointestinal tract. 2-(4-Methoxybenzyl)isothiazolidine 1,1-Dioxide (cas# 158089-76-0) is a useful a reagent in palladium-catalyzed α-arylation of sultams with aryl and heteroaryl iodides.
• Clinical Use: Sulfonamides were formerly much used, alone or in combination with trimethoprim, for the treatment of urinary tract infection, but are no longer recommended because of potential adverse reactions. Use in the treatment of respiratory infections is now confined to a few special problems, notably nocardiasis (and also for cerebral nocardiasis) and, in combination with trimethoprim, in the prevention and treatment of Pneumocystis jirovecii pneumonia. The value of sulfonamides in the prophylaxis and treatment of meningococcal infection is now greatly reduced by bacterial resistance. Sulfonamides are sometimes used for chlamydial infections and chancroid but are unreliable. Some formulations are used topically in eye infections and bacterial vaginosis. Combined preparations with pyrimethamine are used in the treatment of drug-resistant malaria and for toxoplasmosis.

Technology Process of 2-(4-Methoxybenzyl)isothiazolidine 1,1-dioxide

There total 1 articles about 2-(4-Methoxybenzyl)isothiazolidine 1,1-dioxide 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%

isothiazolidine 1,1-dioxide (5908-62-3) + p-methoxybenzyl chloride (824-94-2) → 2-(4-methoxybenzyl)-1,2-isothiazolidine-1,1-dioxide (158089-76-0)

Guidance literature:

With potassium carbonate; In acetonitrile; at 80 ℃; for 12h; Inert atmosphere;

Reference yield: 87.0%

6-iodo-1,4-benzodioxane (57744-67-9) + 2-(4-methoxybenzyl)-1,2-isothiazolidine-1,1-dioxide (158089-76-0) → 5-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2-(4-methoxybenzyl)isothiazolidine 1,1-dioxide (1613639-95-4)

Guidance literature:

With 2,2,6,6-tetramethylpiperidylzinc chloride lithium chloride; bis(dibenzylideneacetone)-palladium⁽⁰⁾; ruphos; In tetrahydrofuran; at 70 ℃; for 16h; Inert atmosphere;

DOI:10.1021/ol501389k

Reference yield: 82.0%

iodobenzene (591-50-4) + 2-(4-methoxybenzyl)-1,2-isothiazolidine-1,1-dioxide (158089-76-0) → 2-(4-methoxybenzyl)-5-phenylisothiazolidine 1,1-dioxide (1613639-91-0)

Guidance literature:

With 2,2,6,6-tetramethylpiperidylzinc chloride lithium chloride; bis(dibenzylideneacetone)-palladium⁽⁰⁾; ruphos; In tetrahydrofuran; at 70 ℃; for 16h; Inert atmosphere;

DOI:10.1021/ol501389k

upstream raw materials:

isothiazolidine 1,1-dioxide

p-methoxybenzyl chloride

Downstream raw materials:

2-(4-methoxybenzyl)-5-phenylisothiazolidine 1,1-dioxide

3-(2-(4-methoxybenzyl)-1,1-dioxidoisothiazolidin-5-yl)benzonitrile

methyl 4-(2-(4-methoxybenzyl)-1,1-dioxidoisothiazolidin-5-yl)benzoate

5-(4-chlorophenyl)-2-(4-methoxybenzyl)isothiazolidine 1,1-dioxide

Refernces