3-(4-Azido-2,3,5,6-tetrafluorobenzoyl)-6-hydroxy-2-(4-hydroxyphenyl)benzo(b)thiophene

Base Information

• Chemical Name: 3-(4-Azido-2,3,5,6-tetrafluorobenzoyl)-6-hydroxy-2-(4-hydroxyphenyl)benzo(b)thiophene
• CAS No.: 131589-59-8
• Molecular Formula: C21H9 F4 N3 O3 S
• Molecular Weight: 459.38
• DSSTox Substance ID: DTXSID80157122
• Nikkaji Number: J392.330D
• Wikidata: Q83025250
• ChEMBL ID: CHEMBL340036
• Mol file: 131589-59-8.mol

Synonyms:3-(4-azido-2,3,5,6-tetrafluorobenzoyl)-6-hydroxy-2-(4-hydroxyphenyl)benzo(b)thiophene;tetrafluoroaryl azide, TFAA

Chemical Property of 3-(4-Azido-2,3,5,6-tetrafluorobenzoyl)-6-hydroxy-2-(4-hydroxyphenyl)benzo(b)thiophene

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 135.52000
• Density: g/cm³
• LogP: 6.16146
• XLogP3: 6.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 4
• Exact Mass: 459.03007498
• Heavy Atom Count: 32
• Complexity: 736

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C2=C(C3=C(S2)C=C(C=C3)O)C(=O)C4=C(C(=C(C(=C4F)F)N=[N+]=[N-])F)F)O

Technology Process of 3-(4-Azido-2,3,5,6-tetrafluorobenzoyl)-6-hydroxy-2-(4-hydroxyphenyl)benzo(b)thiophene

There total 5 articles about 3-(4-Azido-2,3,5,6-tetrafluorobenzoyl)-6-hydroxy-2-(4-hydroxyphenyl)benzo(b)thiophene 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: 80.0%

3-(4-Azido-2,3,5,6-tetrafluorobenzoyl)-6-methoxy-2-(4-methoxyphenyl)benzothiophene (133295-95-1) → 3-(4-Azido-2,3,5,6-tetrafluorobenzoyl)-6-hydroxy-2-(4-hydroxyphenyl)benzothiophene (131589-59-8)

Guidance literature:

With boron dimethyl-trifluoro sulphide; In dichloromethane; at 25 ℃; for 13h; in the dark;

DOI:10.1021/jo00009a037

Reference yield:

4-amino-2,3,5,6-tetrafluorobenzoic acid (944-43-4) → 3-(4-Azido-2,3,5,6-tetrafluorobenzoyl)-6-hydroxy-2-(4-hydroxyphenyl)benzothiophene (131589-59-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) NaNO₂; 2.) NaN₃ / 1.) TFA, 0 deg C, 0.5 h; 2.) Et₂O, 1 h

2: 100 percent / PCl₅ / diethyl ether / 0.17 h

3: 48 percent / AlCl₃, TiCl₄ / CH₂Cl₂ / 24 h / 25 °C

4: 80 percent / BF₃*SMe₂ / CH₂Cl₂ / 13 h / 25 °C / in the dark

With aluminium trichloride; sodium azide; boron dimethyl-trifluoro sulphide; phosphorus pentachloride; titanium tetrachloride; sodium nitrite; In diethyl ether; dichloromethane;

DOI:10.1021/jo00009a037

Reference yield:

4-Azido-2,3,5,6-tetrafluorobenzoyl Chloride (122590-78-7) → 3-(4-Azido-2,3,5,6-tetrafluorobenzoyl)-6-hydroxy-2-(4-hydroxyphenyl)benzothiophene (131589-59-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 48 percent / AlCl₃, TiCl₄ / CH₂Cl₂ / 24 h / 25 °C

2: 80 percent / BF₃*SMe₂ / CH₂Cl₂ / 13 h / 25 °C / in the dark

With aluminium trichloride; boron dimethyl-trifluoro sulphide; titanium tetrachloride; In dichloromethane;

DOI:10.1021/jo00009a037

upstream raw materials:

3-(4-Amino-2,3,5,6-tetrafluorobenzoyl)-6-hydroxy-2-(4-hydroxyphenyl)benzothiophene

3-(4-Azido-2,3,5,6-tetrafluorobenzoyl)-6-methoxy-2-(4-methoxyphenyl)benzothiophene

4-amino-2,3,5,6-tetrafluorobenzoic acid

4-Azido-2,3,5,6-tetrafluorobenzoyl Chloride

Downstream raw materials:

3-(4-Amino-2,3,5,6-tetrafluorobenzoyl)-6-hydroxy-2-(4-hydroxyphenyl)benzothiophene