5-Bromo-5'-methyl-2,2'-bithiophene

Base Information

• Chemical Name: 5-Bromo-5'-methyl-2,2'-bithiophene
• CAS No.: 146796-00-1
• Molecular Formula: C₉H₇BrS₂
• Molecular Weight: 259.191
• DSSTox Substance ID: DTXSID70710785
• Wikidata: Q82646192
• Mol file: 146796-00-1.mol

Synonyms:146796-00-1;5-Bromo-5'-methyl-2,2'-bithiophene;SCHEMBL4090912;DTXSID70710785;UJJLRLVKKPWBLD-UHFFFAOYSA-N;5-Bromo-5'-methyl-2,2'-bithienyl

Chemical Property of 5-Bromo-5'-methyl-2,2'-bithiophene

Chemical Property:

• XLogP3: 4.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 257.91726
• Heavy Atom Count: 12
• Complexity: 163

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(S1)C2=CC=C(S2)Br

Technology Process of 5-Bromo-5'-methyl-2,2'-bithiophene

There total 1 articles about 5-Bromo-5'-methyl-2,2'-bithiophene 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:

5,5'-dibromo-2,2'-bisthiophene (4805-22-5) + methyl trifluoromethanesulfonate (333-27-7) → 5,5'-dimethyl-2,2'-dithiophene (16303-58-5) + 5'-bromo-5-methyl-2,2'-bithiophene (146796-00-1)

Guidance literature:

5,5'-dibromo-2,2'-bisthiophene; With n-butyllithium; In tetrahydrofuran; hexane; at 0 ℃;

methyl trifluoromethanesulfonate; In tetrahydrofuran; hexane; at 0 ℃;

DOI:10.1021/ol8015572

Reference yield: 74.0%

N,N-dimethyl-formamide (68-12-2,33513-42-7) + 5'-bromo-5-methyl-2,2'-bithiophene (146796-00-1) → 5-methyl-2,2'-bithiophene-5'-carboxaldehyde (32358-94-4)

Guidance literature:

5'-bromo-5-methyl-2,2'-bithiophene; With n-butyllithium; In tetrahydrofuran; at -78 - 20 ℃; for 2.5h;

N,N-dimethyl-formamide; In tetrahydrofuran; at -78 ℃; for 1.5h;

DOI:10.1021/ma049102q

Reference yield:

5'-bromo-5-methyl-2,2'-bithiophene (146796-00-1) → 2,3-bis(5,5''-dimethyl-[2,2':5',2''-terthiophen]-4-yl)-4,6-diphenylthieno[3,4-b]thiophene

Guidance literature:

Multi-step reaction with 5 steps

1.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 °C

1.2: 2.08 h / -78 - 20 °C

1.3: 12 h / 80 °C

2.1: n-butyllithium / hexane; tetrahydrofuran; toluene / 4 h / -78 - 20 °C

3.1: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 20 h / 100 °C / Inert atmosphere

4.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 0 - 20 °C / Darkness

5.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide; toluene / 20 h / 100 °C / Inert atmosphere; Schlenk technique

With N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; potassium carbonate; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; toluene; 3.1: |Suzuki Coupling / 5.1: |Stille Cross Coupling;

DOI:10.1021/jacs.8b12617

upstream raw materials:

5,5'-dibromo-2,2'-bisthiophene

methyl trifluoromethanesulfonate

Downstream raw materials:

5-methyl-2,2'-bithiophene-5'-carboxaldehyde