160982-09-2

Basic information

• Product Name: 1-(2-(benzylthio)-5-chlorothiophen-3-yl)ethanone
• Synonyms: 1-[5-Chloro-2-[(phenylMethyl)thio]-3-thienyl]ethanone;1-(2-(benzylthio)-5-chlorothiophen-3-yl)ethanone
• CAS NO: 160982-09-2
• Molecular Formula: C₁₃H₁₁ClOS₂
• Molecular Weight: 282.814
• Product Categories: Intermediates;Sulfur & Selenium Compounds;Aromatics
• Mol File: 160982-09-2.mol

Chemical Properties

• Boiling Point: 407.462 °C at 760 mmHg
• Flash Point: 200.226 °C
• Appearance: /
• Density: 1.33
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 1-(2-(benzylthio)-5-chlorothiophen-3-yl)ethanone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-(benzylthio)-5-chlorothiophen-3-yl)ethanone(160982-09-2)
• EPA Substance Registry System: 1-(2-(benzylthio)-5-chlorothiophen-3-yl)ethanone(160982-09-2)

Safety Data

• Hazardous Substances Data: 160982-09-2(Hazardous Substances Data)

Usage

Uses

1. Used in Pharmaceutical Industry:
1-(2-(Benzylthio)-5-chlorothiophen-3-yl)ethanone is used as a reagent for the preparation of carbonic anhydrase inhibitors. Carbonic anhydrase inhibitors are important in the treatment of various medical conditions, such as glaucoma, altitude sickness, and certain types of seizures. The compound's unique structure allows it to interact with the enzyme carbonic anhydrase, thereby inhibiting its activity and contributing to the development of therapeutic agents.
2. Used in Chemical Research:
As an organic compound with distinct chemical properties, 1-(2-(benzylthio)-5-chlorothiophen-3-yl)ethanone can be utilized in chemical research for the synthesis of various other compounds with potential applications in different fields. Its reactivity and structural features make it a valuable building block for the development of new molecules with specific functions and properties.

Upstream product

• 36157-40-1 3-acetyl-2,5-dichlorothiophene 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 

Downstream Products

• 165117-08-8 3-Acetyl-5-chloro-N-[4-(2-hydroxyethyl)phenyl]-thiophene-2-sulfonamide 
• 160982-10-5 3-acetyl-5-chloro-2-thiophenesulfonamide 
• 171273-41-9 3-Acetyl-5-chloro-N-(4-methoxyphenyl)thiophene-2-sulfonamide 
• 138890-62-7 brinzolamide 
• 160982-11-6 3-(2-Bromoacetyl)-5-chloro-thiophene-2-sulfonamide 
• 160982-16-1 (S)-3,4-dihydro-6-chloro-4-hydroxy-4H-thieno[3,2-e]-1,2-thiazine-1,1-dioxide 
• 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 

Relevant articles and documents

Enantioselective synthesis of brinzolamide (AL-4862), a new topical carbonic anhydrase inhibitor. The "DCAT Route" to thiophenesulfonamides

A large scale synthesis of the topical carbonic anhydrase inhibitors AL-4623A (13a-HCl) and AL-4862 (13b) from 3-acetyl-2,5-dichlorothiophene ("DCAT", 1) is described. Reaction of 1 with NaSBn gave thioether 2, which was converted via sulfenyl chloride 3 and sulfenamide 5 to sulfonamide 6. Bromination of 6 gave bromo ketone 7, which upon reduction with (+)-B-chlorodiisopinocampheylborane and cyclization of the resulting bromohydrin produced S thieno[3,2-e]-1,2-thiazine 8a (96% ee) after chromatography. Treatment of 8a in THF with -BuLi at -70 °C resulted in Li-Cl exchange. Reaction of the thienyllithium with SO2 and hydroxylamine O-sulfonic acid afforded bis-sulfonamide 11a. Protection of lia as the acetimidate 12a, followed by tosylation and animation, gave R amine 13a. The synthesis of 13b proceeded via primary sulfonamide 16, which was brominated, reduced, and cyclized to give S thieno[3,2-e]-1,2-thiazine 18 (>98% ee). By virtue of the ionizable NH, 18 was separable from reduction byproducts by base extraction. Alkylation of 18 with 3-bromopropyl methyl ether afforded 8b, which was converted as above, via lib, to AL-4862 (13b). These procedures provided multihundred gram lots of 13a and 13b.

Carbonic anhydrase inhibitors

Compounds of the following formula are disclosed: Compounds of Formula I are the topic of this invention: STR1 Wherein G, J and the two atoms of the thiophene ring to which they are attached form a six-membered ring chosen from STR2 The compounds are usef

Sulfonamides useful as carbonic anhydrase inhibitors

Sulfonamides and pharmaceutical compositions containing the compounds useful in controlling intraocular pressure are disclosed. Methods for controlling intraocular pressure through administration of the compositions are also disclosed.

Preparation of carbonic anhydrase inhibitors

A process for synthesizing carbonic anhydrase inhibitors is disclosed.