5-Hydroxy-2-benzothiazolesulfonamide

Base Information

• Chemical Name: 5-Hydroxy-2-benzothiazolesulfonamide
• CAS No.: 29927-14-8
• Molecular Formula: C7H6 N2 O3 S2
• Molecular Weight: 0
• Pharos Ligand ID: 9HR2PX6YUXB9
• ChEMBL ID: CHEMBL79738
• Mol file: 29927-14-8.mol

Synonyms:6-hydroxybenzothiazide-2-sulfonamide;L 643,799;L 643799;L-643799

Chemical Property of 5-Hydroxy-2-benzothiazolesulfonamide

Chemical Property:

• Vapor Pressure: 3.92E-11mmHg at 25°C
• Boiling Point: 512.7°C at 760 mmHg
• Flash Point: 263.9°C
• PSA: 129.90000
• Density: 1.723g/cm³
• LogP: 2.43040
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 229.98198440
• Heavy Atom Count: 14
• Complexity: 313

Purity/Quality:

95+% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=C1O)N=C(S2)S(=O)(=O)N

Technology Process of 5-Hydroxy-2-benzothiazolesulfonamide

There total 4 articles about 5-Hydroxy-2-benzothiazolesulfonamide 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: 87.0%

6-ethoxybenzothiazole-2-sulfonamide (452-35-7) → 6-hydroxy-2-benzothiazolesulfonamide (29927-14-8)

Guidance literature:

With aluminum (III) chloride; In dichloromethane; at 0 - 20 ℃;

DOI:10.1016/j.bmc.2015.02.027

Reference yield:

6-ethoxy-2-mercaptobenzothiazole (120-53-6) → 6-hydroxy-2-benzothiazolesulfonamide (29927-14-8)

Guidance literature:

Multi-step reaction with 3 steps

1: conc. NH₄OH, NaOCl, 2.01 M aq. NaOH / 0.25 h / 0 - 5 °C

2: 80 percent / KMnO₄, 1 N H₂SO₄ / acetone; H₂O / 1 h / pH=8.0 - 8.1

3: 66 percent / AlCl₃ / 1,2-dichloro-ethane / 20 h / 25 °C

With ammonium hydroxide; sodium hydroxide; sodium hypochlorite; potassium permanganate; sulfuric acid; aluminium trichloride; In water; 1,2-dichloro-ethane; acetone;

DOI:10.1021/jm00131a011

Reference yield:

6-ethoxy-2-benzothiazolesulfenamide (5304-15-4) → 6-hydroxy-2-benzothiazolesulfonamide (29927-14-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / KMnO₄, 1 N H₂SO₄ / acetone; H₂O / 1 h / pH=8.0 - 8.1

2: 66 percent / AlCl₃ / 1,2-dichloro-ethane / 20 h / 25 °C

With potassium permanganate; sulfuric acid; aluminium trichloride; In water; 1,2-dichloro-ethane; acetone;

DOI:10.1021/jm00131a011

upstream raw materials:

6-ethoxybenzothiazole-2-sulfonamide

2-sulfamoyl-6-benzothiazolyl 2,2-dimethylpropionate

6-ethoxy-2-mercaptobenzothiazole

6-ethoxy-2-benzothiazolesulfenamide

Downstream raw materials:

2-sulfamoyl-6-benzothiazolyl 2-phenylacetate

4-(2-Diethylamino-ethoxy)-benzoic acid 2-sulfamoyl-benzothiazol-6-yl ester

2-sulfamoyl-6-benzothiazolyl benzoate

(2-sulfamoyl-6-benzothiazolyl)2-(4-chlorophenyl) acetate

Refernces

• 1、 -. "DEVELOPMENT OF MOLECULAR IMAGING PROBES FOR CARBONIC ANHYDRASE-IX USING CLICK CHEMISTRY". Page/Page column 51. . Retrieved 2008/12/04.
• 2、 Woltersdorf, O. W.,Schwam, H.,Bicking, J. B.,Brown, S. L.,deSolms, S. J.,et al.. "Topically Active Carbonic Anhydrase Inhibitors. 1. O-Acyl Derivatives of 6-Hydroxybenzothiazole-2-sulfonamide". . p. 2486 - 2492. Retrieved 2007/10/02.