3-(4-Fluorophenyl)thiophene

Base Information

• Chemical Name: 3-(4-Fluorophenyl)thiophene
• CAS No.: 119492-73-8
• Molecular Formula: C10H7FS
• Molecular Weight: 178.23
• DSSTox Substance ID: DTXSID70428358
• Nikkaji Number: J691.360A
• Wikidata: Q82241190
• Mol file: 119492-73-8.mol

Synonyms:3-(4-fluorophenyl)thiophene;119492-73-8;Thiophene, 3-(4-fluorophenyl)-;3-(4-Fluoro-phenyl)-thiophene;3-(4-Fluorophenyl)-Thiophene;SCHEMBL1046660;DTXSID70428358;AKOS004118665;BB 0223659;CS-0268261;EN300-745670

Chemical Property of 3-(4-Fluorophenyl)thiophene

Chemical Property:

• PSA: 28.24000
• LogP: 3.55420
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 178.02524956
• Heavy Atom Count: 12
• Complexity: 141

Purity/Quality:

99% ^*data from raw suppliers

3-(4-Fluorophenyl)thiophene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C2=CSC=C2)F
• Uses: 3-(4-Fluorophenyl)thiophene is an impurity of Canagliflozin (C175190), a sodium/glucose cotransporter 2 (SGLT2) inhibitor. Canagliflozin has been shown to dose dependently reduce calculated renal threshold for glucose excretion and increase urinary glucose excretion. Canagliflozin is a candidate for the treatment of type 2 diabetes and obesity.

Technology Process of 3-(4-Fluorophenyl)thiophene

There total 10 articles about 3-(4-Fluorophenyl)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: 94.0%

Thien-3-ylboronic acid (6165-69-1) + 4-fluoro-1-iodobenzene (352-34-1) → 3-(4-fluorophenyl)thiophene (119492-73-8)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; In water; N,N-dimethyl-formamide; at 85 ℃; Inert atmosphere;

DOI:10.1002/anie.201203792

Reference yield: 91.0%

3-(4'-Hydroxyphenyl)thiophene (29886-67-7) → 3-(4-fluorophenyl)thiophene (119492-73-8)

Guidance literature:

With 1,3-bis(2,6-diisopropylphenyl)-2,2-difluoro-2,3-dihydro-1h-imidazole; cesium fluoride; In toluene; at 23 - 80 ℃; for 18.5h; Inert atmosphere;

DOI:10.1021/ja2048072

Reference yield: 85.0%

3-Bromothiophene (872-31-1) + 4-fluoroboronic acid (1765-93-1) → 3-(4-fluorophenyl)thiophene (119492-73-8)

Guidance literature:

With Tedicyp; potassium carbonate; bis(η3-allyl-μ-chloropalladium(II)); In xylene; at 130 ℃; for 20h;

DOI:10.1016/j.jorganchem.2003.07.005

upstream raw materials:

C₁₀H₇FO₄^(2-)*2Na⁽¹⁺⁾

3-Bromothiophene

4-fluoroboronic acid

3-(4'-Hydroxyphenyl)thiophene

Downstream raw materials:

2-butyl-5-(4-(4-fluorophenyl)thiophen-2-yl)furan

2-bromo-3-(4-fluorophenyl)thiophene

Refernces

• 1、 Chen, Qing-An,He, Gu-Cheng,Hu, Yan-Cheng,Ji, Ding-Wei,Liu, Heng,Zhang, Xiang-Xin,Zhao, Chao-Yang. "Redox-Divergent Construction of (Dihydro)thiophenes with DMSO". supporting information. p. 24284 - 24291. Retrieved 2021/10/08.
• 2、 Gacal, Elif,Denizalt?, Serpil,K?nal, Arma?an,G?k?e, Ayta? Gürhan,Türkmen, Hayati. "Sterically hindered N-aryl/benzyl substituted piperidoimidazolin-2-ylidene palladium complexes and their catalytic activities". . p. 6829 - 6838. Retrieved 2018/10/20.