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

Base Information

• Chemical Name: (S)-6-Chloro-4-hydroxy-3,4-dihydro-2H-thieno[3,2-e][1,2]thiazine 1,1-dioxide
• CAS No.: 160982-16-1
• Molecular Formula: C₆H₆ClNO₃S₂
• Molecular Weight: 239.704
• Hs Code.: 2934999090
• European Community (EC) Number: 870-394-4
• DSSTox Substance ID: DTXSID50471786
• Wikidata: Q72464735
• Mol file: 160982-16-1.mol

Synonyms:160982-16-1;(S)-6-Chloro-4-hydroxy-3,4-dihydro-2H-thieno[3,2-e][1,2]thiazine 1,1-dioxide;(4S)-6-chloro-1,1-dioxo-3,4-dihydro-2H-thieno[3,2-e]thiazin-4-ol;2H-Thieno[3,2-e]-1,2-thiazin-4-ol, 6-chloro-3,4-dihydro-, 1,1-dioxide, (4S)-;(S)-6-Chloro-1,1-dioxo-1,2,3,4-tetrahydro-1lambda*6*-thieno[3,2-e][1,2]thiazin-4-ol;(S)-3,4-Dihydro-6-chloro-4-hydroxy-2H-thieno[3,2-e]-1,2-thiazine-1,1-dioxide;OFJGKGNJDCLNPM-SCSAIBSYSA-N;(4S)-1,1-dioxide-6-chloro-3,4-dihydro-2H-Thieno[3,2-e]-1,2-thiazin-4-ol;SCHEMBL3041948;DTXSID50471786;MFCD09033311;AKOS015897319;DS-16381;C2832;CS-0157325;A51043;(S)-3,4-DIHYDRO-6-CHLORO-4-HYDROXY-2H-T;(4-S)-6-chloro-3,4-dihydro-2H-thieno[3,2-e][1,2]thiazin-4-ol 1,1-dioxide;(S)-6-Chloro-3,4-dihydro-4-hydroxy-2H-thieno[3,2-e]-1,2-thiazine 1,1-dioxide;(S)-6-CHLORO-4-HYDROXY-3,4-DIHYDRO-2H-THIENO-[3,2-E][1,2]THIAZINE 1,1-DIOXIDE;(S)-6-Chloro-4-hydroxy-3,4-dihydro-2H-thieno[3,2-e][1,2]thiazine1,1-dioxide;(4S)-6-Chloro-4-hydroxy-3,4-dihydro-1lambda~6~-thieno[3,2-e][1,2]thiazine-1,1(2H)-dione;138890-89-8

Chemical Property of (S)-6-Chloro-4-hydroxy-3,4-dihydro-2H-thieno[3,2-e][1,2]thiazine 1,1-dioxide

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 128.0 to 132.0 °C
• Refractive Index: 1.664
• Boiling Point: 427.885 °C at 760 mmHg
• PKA: 9.72±0.40(Predicted)
• Flash Point: 212.578 °C
• PSA: 103.02000
• Density: 1.746 g/cm³
• LogP: 2.13640
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility.: soluble in Methanol
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 0
• Exact Mass: 238.9477631
• Heavy Atom Count: 13
• Complexity: 302

Purity/Quality:

99% ^*data from raw suppliers

(S)-6-Chloro-4-hydroxy-3,4-dihydro-2H-thieno[3,2-e][1,2]thiazine 1,1-Dioxide >98.0%(HPLC)(T) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C2=C(SC(=C2)Cl)S(=O)(=O)N1)O
• Isomeric SMILES: C1[C@H](C2=C(SC(=C2)Cl)S(=O)(=O)N1)O

Technology Process of (S)-6-Chloro-4-hydroxy-3,4-dihydro-2H-thieno[3,2-e][1,2]thiazine 1,1-dioxide

There total 6 articles about (S)-6-Chloro-4-hydroxy-3,4-dihydro-2H-thieno[3,2-e][1,2]thiazine 1,1-dioxide 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: 77.0%

3-(2-Bromoacetyl)-5-chloro-thiophene-2-sulfonamide (160982-11-6) → (S)-3,4-dihydro-6-chloro-4-hydroxy-4H-thieno[3,2-e]-1,2-thiazine-1,1-dioxide (160982-16-1,171274-01-4)

Guidance literature:

3-(2-Bromoacetyl)-5-chloro-thiophene-2-sulfonamide; With B-chlorodiisopinocampheylborane; In tert-butyl methyl ether; at -40 - -32 ℃; for 3.5h; Inert atmosphere;

With sodium hydroxide; In tert-butyl methyl ether; water; at 0 - 22 ℃; for 2h; enantioselective reaction;

DOI:10.1021/op9802125

Reference yield:

3-(2-Bromoacetyl)-5-chloro-thiophene-2-sulfonamide (160982-11-6) + (+)-β-chlorodiisopino-campheylborane + tert-butyl methyl ether (1634-04-4) + carbon dioxide (124-38-9,18923-20-1) → (S)-3,4-dihydro-6-chloro-4-hydroxy-4H-thieno[3,2-e]-1,2-thiazine-1,1-dioxide (160982-16-1,171274-01-4)

Guidance literature:

With hydrogenchloride; sodium hydroxide; In toluene;

Reference yield:

3-acetyl-5-chloro-2-thiophenesulfenamide → (S)-3,4-dihydro-6-chloro-4-hydroxy-4H-thieno[3,2-e]-1,2-thiazine-1,1-dioxide (160982-16-1,171274-01-4)

Guidance literature:

Multi-step reaction with 3 steps

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

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

3.1: B-chlorodiisopinocampheylborane / tert-butyl methyl ether / 3.5 h / -40 - -32 °C / Inert atmosphere

3.2: 2 h / 0 - 22 °C

With sodium tungstate (VI) dihydrate; pyridinium hydrobromide perbromide; sulfuric acid; dihydrogen peroxide; B-chlorodiisopinocampheylborane; In tert-butyl methyl ether; water; ethyl acetate;

DOI:10.1021/op9802125

upstream raw materials:

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

tert-butyl methyl ether

carbon dioxide

3-acetyl-2,5-dichlorothiophene

Downstream raw materials:

2-(3-methoxypropyl)-2H-thieno[3,2-e]-1,2-thiazine-6-sulfonamine 1,1-dioxide

brinzolamide

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

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