3-Acetyl-5-chlorothiophene-2-sulfonamide

Base Information

• Chemical Name: 3-Acetyl-5-chlorothiophene-2-sulfonamide
• CAS No.: 160982-10-5
• Molecular Formula: C₆H₆ClNO₃S₂
• Molecular Weight: 239.704
• Hs Code.: 2935009090
• DSSTox Substance ID: DTXSID90571092
• Wikidata: Q72434986
• Mol file: 160982-10-5.mol

Synonyms:3-ACETYL-5-CHLOROTHIOPHENE-2-SULFONAMIDE;160982-10-5;3-Acetyl-2-(aminosulfonyl)-5-chlorothiophene;3-ACETYL-5-CHLORO-2-THIOPHENESULFONAMIDE;2-Thiophenesulfonamide, 3-acetyl-5-chloro-;MFCD09033309;2-Thiophenesulfonamide,3-acetyl-5-chloro-;SCHEMBL2631260;DTXSID90571092;ODLFFSHLXVZFPY-UHFFFAOYSA-N;AMY19478;AKOS015909945;AB49386;DS-4144;3-acetyl-5-chloro-2thiophenesulfonamide;AC-27013;SY055529;CS-0155128;EN300-278416;T70363;A883155

Chemical Property of 3-Acetyl-5-chlorothiophene-2-sulfonamide

Chemical Property:

• Vapor Pressure: 2.15E-08mmHg at 25°C
• Melting Point: 182 °C(dec.)
• Boiling Point: 453oC at 760 mmHg
• PKA: 9.29±0.60(Predicted)
• Flash Point: 227.7oC
• PSA: 113.85000
• Density: 1.583
• LogP: 3.03260
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility.: soluble in Methanol
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 238.9477631
• Heavy Atom Count: 13
• Complexity: 310

Purity/Quality:

98%, ^*data from raw suppliers

3-Acetyl-5-chloro-2-thiophenesulfonamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=O)C1=C(SC(=C1)Cl)S(=O)(=O)N
• Uses: 3-Acetyl-5-chlorothiophene-2-sulfonamide is a reactant used in the preparation of heteroaryl chalcones as potent antimicrobial agents and Brinzolamide (B677600), a topical carbonic anhydrase inhibitors.

Technology Process of 3-Acetyl-5-chlorothiophene-2-sulfonamide

There total 6 articles about 3-Acetyl-5-chlorothiophene-2-sulfonamide 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: 91.2%

3-acetyl-5-chloro-2-thiophenesulfonyl chloride → 3-acetyl-5-chloro-2-thiophenesulfonamide (160982-10-5)

Guidance literature:

With ammonia; In ethyl acetate; at 0 - 15 ℃; for 1h; Reagent/catalyst;

Reference yield:

sodium tungstate (VI) dihydrate (10213-10-2) + 3-Acetyl-2-(phenylmethyl)thio-5-chlorothiophene (160982-09-2) → 3-acetyl-5-chloro-2-thiophenesulfonamide (160982-10-5)

Guidance literature:

With dihydrogen peroxide; sodium hydrogensulfite; In water; ethyl acetate;

Reference yield:

3-acetyl-5-chloro-2-thiophenesulfenamide → 3-acetyl-5-chloro-2-thiophenesulfonamide (160982-10-5)

Guidance literature:

With sodium tungstate (VI) dihydrate; dihydrogen peroxide; In water; at 15 - 35 ℃; for 19h;

DOI:10.1021/op9802125

upstream raw materials:

sodium tungstate (VI) dihydrate

3-Acetyl-2-(phenylmethyl)thio-5-chlorothiophene

3-acetyl-2,5-dichlorothiophene

Downstream raw materials:

brinzolamide

(S)-3,4-dihydro-6-chloro-4-hydroxy-2-(3-methoxypropyl)-4H-thieno[3,2-e]-1,2-thiazine 1,1-dioxide

(S)-3,4-dihydro-4-hydroxy-2(3-methoxypropyl)-4H-thieno[3,2-e]-1,2-thiazine-6-sulfonamide-1,1-dioxide

3-(2-Bromoacetyl)-5-chloro-thiophene-2-sulfonamide

Refernces

• 1、 Conrow, Raymond E.,Dean, W. Dennis,Zinke, Paul W.,Deason, Michael E.,Sproull, Steven J.,Dantanarayana, Anura P.,DuPriest, Mark T.. "Enantioselective synthesis of brinzolamide (AL-4862), a new topical carbonic anhydrase inhibitor. The "DCAT Route" to thiophenesulfonamides". . p. 114 - 120. Retrieved 2013/09/08.