Thioflosulide

Base Information

• Chemical Name: Thioflosulide
• CAS No.: 158205-05-1
• Molecular Formula: C16H13 F2 N O3 S2
• Molecular Weight: 369.413
• Nikkaji Number: J621.412F
• Pharos Ligand ID: GMFWN47NXM5M
• ChEMBL ID: CHEMBL287919
• Mol file: 158205-05-1.mol

Synonyms:5-methanesulfonamido-6-(2,4-difluorothiophenyl)-1-indanone;L 745,337;L 745337;L-745,337;L-745337

Chemical Property of Thioflosulide

Chemical Property:

• Boiling Point: 495.8±55.0 °C(Predicted)
• PSA: 96.92000
• Density: 1.52±0.1 g/cm3(Predicted)
• LogP: 4.77020
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 369.03049195
• Heavy Atom Count: 24
• Complexity: 580

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CS(=O)(=O)NC1=C(C=C2C(=C1)CCC2=O)SC3=C(C=C(C=C3)F)F

Technology Process of Thioflosulide

There total 16 articles about Thioflosulide 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%

5--6-(2,4-difluorophenylthio)-1-indanone (170456-58-3) → 5-methanesulfonamido-6-(2,4-difluorophenylthio)-1-indanone (158205-05-1)

Guidance literature:

With potassium carbonate; In tetrahydrofuran; methanol; for 1h; Ambient temperature;

DOI:10.1080/00397919508011826

Reference yield: 76.0%

methanesulfonyl chloride (124-63-0) + 5-amino-6-<(2,4-difluorophenyl)thio>-1-indanone (158205-23-3) → 5-methanesulfonamido-6-(2,4-difluorophenylthio)-1-indanone (158205-05-1)

Guidance literature:

With sodium hydroxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane;

Reference yield:

5-acetylamino-6-bromoindane (157701-33-2) → 5-methanesulfonamido-6-(2,4-difluorophenylthio)-1-indanone (158205-05-1)

Guidance literature:

Multi-step reaction with 8 steps

1: 80 percent / CrO₃, HOAc / 0.25 h / 50 - 55 °C

2: 100 percent / 6 M aq. HCl / 1 h / Heating

3: 51 percent / 1.) 20percent aq. HBF₄, 4 M NaNO₂, 2.) Cu, NaNO₂ / 0.5 h / Ambient temperature

4: 79 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 2 h / Ambient temperature

5: 81 percent / pyridine, 8 M aq. KOH / 2 h / Ambient temperature

6: 81 percent / iron, NH₄Cl / ethanol; H₂O / 1 h / Heating

7: Et₃N / CH₂Cl₂ / 1 h / Ambient temperature

8: 10 M aq. NaOH / 0.5 h / Ambient temperature

With pyridine; chromium(VI) oxide; hydrogenchloride; potassium hydroxide; sodium hydroxide; tetrafluoroboric acid; trimethylsilyl trifluoromethanesulfonate; iron; copper; ammonium chloride; acetic acid; triethylamine; sodium nitrite; In ethanol; dichloromethane; water;

DOI:10.1021/jm00025a007

upstream raw materials:

5--6-(2,4-difluorophenylthio)-1-indanone

indan-5-amine

5-acetylamino-6-bromoindane

5-acetamidoindane

Refernces

• 1、 -. "Antiangiogenic combination therapy for the treatment of cancer". . . Retrieved 2008/06/13.
• 2、 Scheigetz,Zamboni,Roy. "Synthesis of 5-methanesulfonamido-6-(2,4-difluorophenylthio)-1-indanone". . p. 2791 - 2806. Retrieved 2007/10/02.