3-(2-Bromoacetyl)-5-chlorothiophene-2-sulfonamide

Base Information

• Chemical Name: 3-(2-Bromoacetyl)-5-chlorothiophene-2-sulfonamide
• CAS No.: 160982-11-6
• Molecular Formula: C₆H₅BrClNO₃S₂
• Molecular Weight: 318.6
• Hs Code.: 2935009090
• European Community (EC) Number: 605-241-0
• DSSTox Substance ID: DTXSID50430974
• Wikidata: Q72451252
• Mol file: 160982-11-6.mol

Synonyms:3-(2-Bromoacetyl)-5-chlorothiophene-2-sulfonamide;160982-11-6;3-(2-BROMOACETYL)-5-CHLORO-2-THIOPHENESULFONAMIDE;2-Thiophenesulfonamide, 3-(2-bromoacetyl)-5-chloro-;3-(Bromoacetyl)-5-chlorothiophene-2-sulfonamide;C6H5BrClNO3S2;3-(2-Bromo-acetyl)-5-chloro-thiophene-2-sulfonic acid amide;2-Thiophenesulfonamide,3-(2-bromoacetyl)-5-chloro-;SCHEMBL1559488;DTXSID50430974;OZESFFKYLOCAOV-UHFFFAOYSA-N;BCP06627;MFCD09033310;AKOS015895859;AB49389;AC-22718;BS-16043;CS-0157327;FT-0696025;3-bromoacetyl-5-chloro-2-thiophenesulfonamide;D82428;A883154

Chemical Property of 3-(2-Bromoacetyl)-5-chlorothiophene-2-sulfonamide

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.64
• Boiling Point: 492.247 °C at 760 mmHg
• PKA: 9.21±0.60(Predicted)
• Flash Point: 251.502 °C
• PSA: 113.85000
• Density: 1.936 g/cm³
• LogP: 3.40760
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 316.85828
• Heavy Atom Count: 14
• Complexity: 329

Purity/Quality:

99% ^*data from raw suppliers

3-(Bromoacetyl)-5-chloro-2-thiophenesulfonamide 95.0% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(SC(=C1C(=O)CBr)S(=O)(=O)N)Cl

Technology Process of 3-(2-Bromoacetyl)-5-chlorothiophene-2-sulfonamide

There total 5 articles about 3-(2-Bromoacetyl)-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: 96.8%

3-acetyl-5-chloro-2-thiophenesulfonamide (160982-10-5) → 3-(2-Bromoacetyl)-5-chloro-thiophene-2-sulfonamide (160982-11-6)

Guidance literature:

With N-Bromosuccinimide; In ethyl acetate; at 60 - 70 ℃; Solvent; Temperature; Large scale;

Reference yield:

3-acetyl-5-chloro-2-thiophenesulfenamide → 3-(2-Bromoacetyl)-5-chloro-thiophene-2-sulfonamide (160982-11-6)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium tungstate (VI) dihydrate; dihydrogen peroxide / water / 19 h / 15 - 35 °C

2: pyridinium hydrobromide perbromide; sulfuric acid / ethyl acetate / 1.5 h / 1 - 5 °C / Large scale

With sodium tungstate (VI) dihydrate; pyridinium hydrobromide perbromide; sulfuric acid; dihydrogen peroxide; In water; ethyl acetate;

DOI:10.1021/op9802125

Reference yield:

3-acetyl-2,5-dichlorothiophene (36157-40-1) → 3-(2-Bromoacetyl)-5-chloro-thiophene-2-sulfonamide (160982-11-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: thiourea / ethanol; water / 2 h / Reflux; Large scale

1.2: 3 h / Reflux; Large scale

2.1: chlorine / toluene / 0.42 h / 8 °C / Cooling with ice

3.1: ammonia / 1 h / 5 - 15 °C

4.1: sodium tungstate (VI) dihydrate; dihydrogen peroxide / water / 19 h / 15 - 35 °C

5.1: pyridinium hydrobromide perbromide; sulfuric acid / ethyl acetate / 1.5 h / 1 - 5 °C / Large scale

With sodium tungstate (VI) dihydrate; pyridinium hydrobromide perbromide; sulfuric acid; ammonia; dihydrogen peroxide; chlorine; thiourea; In ethanol; water; ethyl acetate; toluene;

DOI:10.1021/op9802125

upstream raw materials:

3-acetyl-5-chloro-2-thiophenesulfonamide

3-acetyl-2,5-dichlorothiophene

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

Downstream raw materials:

brinzolamide

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

(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

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.
• 2、 -. "Preparation of carbonic anhydrase inhibitors". . . Retrieved 2008/06/13.