160982-10-5

Basic information

• Product Name: 3-Acetyl-5-chlorothiophene-2-sulfonamide
• Synonyms: 3-Acetyl-5-chlorothiophene-2-sulfonamide;3-Acetyl-2-(aMinosulfonyl)-5-chlorothiophene;2-Thiophenesulfonamide, 3-Acetyl-5-Chloro-;2-Thiophenesulfonamide,3-Acetyl-5-Chloro-
• CAS NO: 160982-10-5
• Molecular Formula: C6H6ClNO3S2
• Molecular Weight: 239.702
• EINECS: 1308068-626-2
• Mol File: 160982-10-5.mol
• Article Data: 3

Chemical Properties

• Melting Point: 182 °C(dec.)
• Boiling Point: 453°C at 760 mmHg
• Flash Point: 227.7°C
• Appearance: /
• Density: 1.583
• Vapor Pressure: 2.15E-08mmHg at 25°C
• Refractive Index: 1.596
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility: soluble in Methanol
• PKA: 9.29±0.60(Predicted)
• CAS DataBase Reference: 3-Acetyl-5-chlorothiophene-2-sulfonamide(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Acetyl-5-chlorothiophene-2-sulfonamide(160982-10-5)
• EPA Substance Registry System: 3-Acetyl-5-chlorothiophene-2-sulfonamide(160982-10-5)

Safety Data

• Hazardous Substances Data: 160982-10-5(Hazardous Substances Data)

Usage

Description

3-Acetyl-5-chlorothiophene-2-sulfonamide is an organic compound characterized by its off-white solid appearance. It is a chemical intermediate that plays a significant role in the synthesis of various pharmaceutical compounds due to its unique chemical structure.

Uses

Used in Pharmaceutical Industry:
3-Acetyl-5-chlorothiophene-2-sulfonamide is used as a reactant for the preparation of heteroaryl chalcones, which are potent antimicrobial agents. These agents are crucial in the development of new drugs to combat bacterial infections, especially in the context of increasing antibiotic resistance.
Additionally, 3-Acetyl-5-chlorothiophene-2-sulfonamide is used as a reactant in the synthesis of Brinzolamide (B677600), a topical carbonic anhydrase inhibitor. 3-Acetyl-5-chlorothiophene-2-sulfonamide is utilized in the treatment of certain eye conditions, such as glaucoma, by reducing intraocular pressure.

InChI:InChI=1/C6H6ClNO3S2/c1-3(9)4-2-5(7)12-6(4)13(8,10)11/h2H,1H3,(H2,8,10,11)

Upstream product

• 10213-10-2 sodium tungstate (VI) dihydrate 
• 160982-09-2 3-Acetyl-2-(phenylmethyl)thio-5-chlorothiophene 
• 36157-40-1 3-acetyl-2,5-dichlorothiophene 

Downstream Products

• 138890-62-7 brinzolamide 
• 160982-13-8 (S)-3,4-dihydro-6-chloro-4-hydroxy-2-(3-methoxypropyl)-4H-thieno[3,2-e]-1,2-thiazine 1,1-dioxide 
• 154127-42-1 (S)-3,4-dihydro-4-hydroxy-2(3-methoxypropyl)-4H-thieno[3,2-e]-1,2-thiazine-6-sulfonamide-1,1-dioxide 
• 160982-11-6 3-(2-Bromoacetyl)-5-chloro-thiophene-2-sulfonamide 

Relevant articles and documents

Thiophene sulfonaide breene assists the amine process for the preparation of intermediates

The invention belongs to the technical field of pharmaceutical chemicals, in particular relates to a method for preparing an intermediate thiophene sulfonamide of brinzolamide and is applicable to industrial production. The method comprises the following steps: dissolving thiophene benzyl sulfide in a proper solvent, adding glacial acetic acid and water, controlling the temperature to 0-15 DEG C, adding trichloroisocyanuric acid in batches in 20-40 minutes, reacting at the constant temperature until the raw materials disappear, performing vacuum concentration in a water bath at the temperature of 30-50 DEG C to remove the solvent, adding ethyl acetate petroleum ether solution with the mass concentration of ethyl acetate being 25%, stirring, filtering, evaporating the filtrate under reduced pressure, thereby obtaining thiophenesulfonyl chloride; controlling the temperature to 0-15 DEG C, diluting thiophenesulfonyl chloride by ethyl acetate, dropwise adding a dilution into ammonium hydroxide or a water solution of amine, stirring and reacting until the raw materials disappear, filtering, washing, drying the solids, and obtaining the thiophene sulfonamide. The product obtained by using the method is high in yield, simple and convenient in operation, low in cost and mild in reaction conditions and is suitable for large-scale production.

Preparation of carbonic anhydrase inhibitors

A process for synthesizing carbonic anhydrase inhibitors is disclosed.