3-(3-Oxo-1,2-benzisothiazol-2(3H)-yl)propanoic acid

Base Information

• Chemical Name: 3-(3-Oxo-1,2-benzisothiazol-2(3H)-yl)propanoic acid
• CAS No.: 89139-48-0
• Molecular Formula: C10H9NO3S
• Molecular Weight: 223.24800
• Mol file: 89139-48-0.mol

Synonyms:3-(1,2-Benzisothiazolin-3-on-2-yl)propionsaeure;1,2-Benzisothiazole-2(3H)-propanoic acid,3-oxo;BB_SC-7772;3-(3-oxo-1,2-benzothiazol-2(3H)-yl)propanoic acid;

Chemical Property of 3-(3-Oxo-1,2-benzisothiazol-2(3H)-yl)propanoic acid

Chemical Property:

• PSA: 87.54000
• LogP: 1.53770

Purity/Quality:

99% ^*data from raw suppliers

3-(3-Oxo-1,2-benzisothiazol-2(3H)-yl)propanoic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(3-Oxo-1,2-benzisothiazol-2(3H)-yl)propanoic acid

There total 13 articles about 3-(3-Oxo-1,2-benzisothiazol-2(3H)-yl)propanoic acid 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: 75.0%

methyl 3-(3-oxobenzisothiazol-2(3H)-yl)propanoate → 3-(3-oxobenzo[d]isothiazol-2(3H)-yl)propanoic acid (89139-48-0)

Guidance literature:

With lithium hydroxide; In 1,4-dioxane; water; for 16h;

DOI:10.1016/j.tet.2017.02.025

Reference yield: 59.0%

3-Bromopropionic acid (590-92-1) + 1,2-benzisothiazolin-3-one (2634-33-5) → 3-(3-oxobenzo[d]isothiazol-2(3H)-yl)propanoic acid (89139-48-0)

Guidance literature:

With sodium hydroxide; In water; for 6h; Heating;

Reference yield:

Thiosalicylic acid (147-93-3) → 3-(3-oxobenzo[d]isothiazol-2(3H)-yl)propanoic acid (89139-48-0)

Guidance literature:

Multi-step reaction with 5 steps

1: sulfuric acid / Reflux

2: bromine / tetrachloromethane / 1 h / 0 - 20 °C

3: bromine / tetrachloromethane / 1 h / 20 °C

4: triethylamine / tetrachloromethane / 5 h / 20 °C / Reflux

5: lithium hydroxide / water; 1,4-dioxane / 16 h

With sulfuric acid; bromine; triethylamine; lithium hydroxide; In 1,4-dioxane; tetrachloromethane; water;

DOI:10.1016/j.tet.2017.02.025

upstream raw materials:

3-Bromopropionic acid

1,2-benzisothiazolin-3-one

2-chlorosulfenylbenzoyl chloride

3-amino propanoic acid

Downstream raw materials:

2,2'-Dithio-bis

N-[(Dibenzylamino)-methyl]-3-(3-oxo-3H-benzo[d]isothiazol-2-yl)-propionamide

Refernces

• 1、 Viani, Fiorenza,Rossi, Bianca,Panzeri, Walter,Merlini, Luca,Martorana, Alessandra M.,Polissi, Alessandra,Galante, Yves M.. "Synthesis and anti-bacterial activity of a library of 1,2-benzisothiazol-3(2H)-one (BIT) derivatives amenable of crosslinking to polysaccharides". . p. 1745 - 1761. Retrieved 2017/03/08.
• 2、 Maggiali,Mingiardi,Branca,Ricci. "Biological properties of 1,2-benzisothiazole derivatives - Auxin activity in flax roots of 3-oxo-1,2-benzisothiazolin-2-ylalkanoic acids". . p. 935 - 939. Retrieved 2007/10/02.