2,5-Diphenylthiophene 1,1-dioxide

Base Information

• Chemical Name: 2,5-Diphenylthiophene 1,1-dioxide
• CAS No.: 51092-02-5
• Molecular Formula: C16H12O2S
• Molecular Weight: 268.336
• DSSTox Substance ID: DTXSID80480801
• Nikkaji Number: J902.262G
• Wikidata: Q82315881
• Mol file: 51092-02-5.mol

Synonyms:2,5-Diphenylthiophene 1,1-dioxide;51092-02-5;Thiophene, 2,5-diphenyl-, 1,1-dioxide;SCHEMBL6309408;DTXSID80480801

Chemical Property of 2,5-Diphenylthiophene 1,1-dioxide

Chemical Property:

• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 268.05580079
• Heavy Atom Count: 19
• Complexity: 441

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=CC=C(S2(=O)=O)C3=CC=CC=C3

Technology Process of 2,5-Diphenylthiophene 1,1-dioxide

There total 6 articles about 2,5-Diphenylthiophene 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: 83.0%

2,5-Diphenyl-thiophene (1445-78-9) → 2,5-bis(phenyl)-thiophene-1,1-dioxide (51092-02-5)

Guidance literature:

With 3,3-dimethyldioxirane; In dichloromethane; acetone;

DOI:10.1002/jhet.5570340530

Reference yield: 10.0%

trimethyl(phenyl)stannane (934-56-5) + 2,5-diiodothiophene-1,1-dioxide (143810-43-9) → 2,5-bis(phenyl)-thiophene-1,1-dioxide (51092-02-5)

Guidance literature:

2,5-diiodothiophene-1,1-dioxide; With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; triphenyl-arsane; In 1,4-dioxane; for 0.166667h; Inert atmosphere; Sealed tube;

trimethyl(phenyl)stannane; In 1,4-dioxane; at 100 ℃; for 6h; Inert atmosphere; Sealed tube;

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; triphenyl-arsane; In 1,4-dioxane; at 100 ℃; Inert atmosphere; Sealed tube;

DOI:10.1021/ol4024024

Reference yield:

phenylmagnesium bromide (100-58-3) → 2,5-bis(phenyl)-thiophene-1,1-dioxide (51092-02-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: diethyl ether / Schlenk technique; Inert atmosphere; Reflux

2.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; triphenyl-arsane / 1,4-dioxane / 0.17 h / Inert atmosphere; Sealed tube

2.2: 6 h / 100 °C / Inert atmosphere; Sealed tube

2.3: 100 °C / Inert atmosphere; Sealed tube

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; triphenyl-arsane; In 1,4-dioxane; diethyl ether; 2.1: |Stille Cross Coupling / 2.2: |Stille Cross Coupling / 2.3: |Stille Cross Coupling;

DOI:10.1021/ol4024024

upstream raw materials:

2,5-Diphenyl-thiophene

phenacylacetophenone

trimethyl(phenyl)stannane

2,5-diiodothiophene-1,1-dioxide

Downstream raw materials:

1,2,4-triphenylbenzene

tricarbonyl(η4-2,5-diphenylthiophene dioxide)iron

1,4-diphenylnaphthalene