5'-Bromo-[2,2'-bithiophene]-5-carbonitrile

Base Information

• Chemical Name: 5'-Bromo-[2,2'-bithiophene]-5-carbonitrile
• CAS No.: 176787-96-5
• Molecular Formula: C9H4BrNS2
• Molecular Weight: 270.173
• European Community (EC) Number: 834-594-5
• Nikkaji Number: J730.338F
• Mol file: 176787-96-5.mol

Synonyms:5'-bromo-[2,2'-bithiophene]-5-carbonitrile;176787-96-5;5-(5-bromothiophen-2-yl)thiophene-2-carbonitrile;BHA78796;MFCD16339405;B5457;CS-0378075;T70438;5 inverted exclamation marka-Bromo[2,2 inverted exclamation marka-bithiophene]-5-carbonitrile

Chemical Property of 5'-Bromo-[2,2'-bithiophene]-5-carbonitrile

Chemical Property:

• Melting Point: 161.0 to 165.0 °C
• Boiling Point: 352.0±42.0 °C(Predicted)
• PSA: 80.27000
• Density: 1.76±0.1 g/cm3(Predicted)
• LogP: 4.11078
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 268.89685
• Heavy Atom Count: 13
• Complexity: 237

Purity/Quality:

97% ^*data from raw suppliers

5-Bromo-2,2''-bithiophene-5''-carbonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(SC(=C1)C2=CC=C(S2)Br)C#N
• Uses: 5-Bromo-2,2''-bithiophene-5''-carbonitrile acts as a reagent in the synthesis of dicationic phenyl-2,2''-bichalcophenes and analogs as antiprotozoal agents.

Technology Process of 5'-Bromo-[2,2'-bithiophene]-5-carbonitrile

There total 4 articles about 5'-Bromo-[2,2'-bithiophene]-5-carbonitrile 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: 95.0%

2,2’-bithiophene-5-carbonitrile (16278-99-2) → 5-bromo-2,2’-bithiophene-5’-carbonitrile (176787-96-5)

Guidance literature:

With N-Bromosuccinimide; In N,N-dimethyl-formamide;

Reference yield:

5-bromo-2-thiophencarboxaldehyde (4701-17-1) → 5-bromo-2,2’-bithiophene-5’-carbonitrile (176787-96-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 85 percent / Pd(PPh₃)4 / dioxane / 24 h / 80 - 90 °C

2: aq. NH₂OH*HCl; Na₂CO₃ / methanol / 6 h / Heating

3: Ac₂O / 4 h / Heating

4: 95 percent / N-bromosuccinimide / dimethylformamide

With N-Bromosuccinimide; hydroxylamine hydrochloride; acetic anhydride; sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,4-dioxane; methanol; N,N-dimethyl-formamide; 1: Stille coupling;

Reference yield:

2,2'-bithiophene-5-carboxaldehyde (3779-27-9) → 5-bromo-2,2’-bithiophene-5’-carbonitrile (176787-96-5)

Guidance literature:

Multi-step reaction with 3 steps

1: aq. NH₂OH*HCl; Na₂CO₃ / methanol / 6 h / Heating

2: Ac₂O / 4 h / Heating

3: 95 percent / N-bromosuccinimide / dimethylformamide

With N-Bromosuccinimide; hydroxylamine hydrochloride; acetic anhydride; sodium carbonate; In methanol; N,N-dimethyl-formamide;

upstream raw materials:

2,2’-bithiophene-5-carbonitrile

5-bromo-2-thiophencarboxaldehyde

2,2'-bithiophene-5-carboxaldehyde

2,2'-bithiophene-5-carbaldoxime