3-Phenyl-1,2-benzisothiazole 1,1-dioxide

Base Information

• Chemical Name: 3-Phenyl-1,2-benzisothiazole 1,1-dioxide
• CAS No.: 53440-57-6
• Molecular Formula: C13H9NO2S
• Molecular Weight: 243.286
• DSSTox Substance ID: DTXSID20358575
• Nikkaji Number: J283.806K
• Wikidata: Q82139229
• ChEMBL ID: CHEMBL2140499
• Mol file: 53440-57-6.mol

Synonyms:3-phenyl-1,2-benzisothiazole 1,1-dioxide;53440-57-6;3-phenyl-1,2-benzothiazole 1,1-dioxide;1,2-Benzisothiazole, 3-phenyl-, 1,1-dioxide;MLS001179335;SCHEMBL7638951;CHEMBL2140499;DTXSID20358575;HMS2778D08;SMR000476579;3-phenyl-benzo[d]isothiazole 1,1-dioxide;E84965;3-PHENYLBENZO[D]ISOTHIAZOLE 1,1-DIOXIDE;AK-830/13217029

Chemical Property of 3-Phenyl-1,2-benzisothiazole 1,1-dioxide

Chemical Property:

• Melting Point: 315 °C
• Boiling Point: 438.6±28.0 °C(Predicted)
• PKA: -4.09±0.20(Predicted)
• PSA: 54.88000
• Density: 1.34±0.1 g/cm3(Predicted)
• LogP: 2.74270
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 243.03539970
• Heavy Atom Count: 17
• Complexity: 415

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=NS(=O)(=O)C3=CC=CC=C32

Technology Process of 3-Phenyl-1,2-benzisothiazole 1,1-dioxide

There total 30 articles about 3-Phenyl-1,2-benzisothiazole 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: 98.0%

(±)-3-phenyl-1,2-benzisothiazoline 1,1-dioxide (136701-86-5) → 3-phenylbenzo[d]isothiazole-1,1-dioxide (53440-57-6)

Guidance literature:

With potassium fluoride dihydrate; [Ir(ppy)₂(dtbbpy)]PF₆; In acetonitrile; at 20 ℃; for 12h; Reagent/catalyst; Solvent; Irradiation;

DOI:10.1016/j.tetlet.2020.152059

Reference yield: 96.0%

3-ethoxy-benzo[d]isothiazole 1,1-dioxide (18712-15-7) + phenyllithium (591-51-5) → 3-phenylbenzo[d]isothiazole-1,1-dioxide (53440-57-6)

Guidance literature:

In tetrahydrofuran; at -78 ℃; for 4h;

DOI:10.1021/jo00291a028

Reference yield: 93.0%

phenylmagnesium bromide (100-58-3) + saccharin (81-07-2) → 3-phenylbenzo[d]isothiazole-1,1-dioxide (53440-57-6)

Guidance literature:

phenylmagnesium bromide; saccharin; In tetrahydrofuran; at 25 ℃; Schlenk technique; Inert atmosphere;

With toluene-4-sulfonic acid; In tetrahydrofuran; toluene; Schlenk technique; Inert atmosphere; Reflux;

DOI:10.1039/c8cc01284a

upstream raw materials:

2-benzoyl-benzenesulfonyl chloride

benzene

benzophenone

2-benzoyl-benzenesulfonyl azide

Downstream raw materials:

2-((Z)-3-Diethylamino-2-methyl-1-phenyl-propenyl)-benzenesulfonamide

N-tert-butyl-2-(α-hydroxybenzyl)benzenesulphonamide

1,9b-diphenyl-1,2-dihydrobenzo[d]pyrrolo[1,2-b]isothiazol-3-one 5,5-dioxide

C₂₂H₂₁NO₅S

Refernces

• 1、 Delost, Michael D.,Njardarson, Jon T.. "Mild Darzens Annulations for the Assembly of Trifluoromethylthiolated (SCF3) Aziridine and Cyclopropane Structures". supporting information. p. 6121 - 6125. Retrieved 2021/08/16.
• 2、 Ming, Zong-Yao,Li, Kang-Rui,Meng, Fan-Jie,Shi, Lei,Jiang, Wen-Feng. "Efficient visible-light photocatalytic aerobic oxidation of cyclic sulfamides to imines". supporting information. . Retrieved 2020/06/17.