5-(3-Chlorophenyl)thiophene-2-carbaldehyde

Base Information

• Chemical Name: 5-(3-Chlorophenyl)thiophene-2-carbaldehyde
• CAS No.: 51081-72-2
• Molecular Formula: C₁₁H₇ClOS
• Molecular Weight: 222.695
• European Community (EC) Number: 827-596-2
• Mol file: 51081-72-2.mol

Synonyms:5-(3-chlorophenyl)thiophene-2-carbaldehyde;51081-72-2;5-(3-Chloro-phenyl)-thiophene-2-carbaldehyde;SCHEMBL2019002;AKOS004113905;AB24061;5-(3-chlorophenyl)-2-thiophenecarbaldehyde;BB 0222848;CS-0247097;EN300-35666;Z361292092

Chemical Property of 5-(3-Chlorophenyl)thiophene-2-carbaldehyde

Chemical Property:

• XLogP3: 3.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 221.9906137
• Heavy Atom Count: 14
• Complexity: 210

Purity/Quality:

97% ^*data from raw suppliers

5-(3-chlorophenyl)thiophene-2-carbaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

Technology Process of 5-(3-Chlorophenyl)thiophene-2-carbaldehyde

There total 4 articles about 5-(3-Chlorophenyl)thiophene-2-carbaldehyde 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: 53.0%

thiophene-2-carbaldehyde (98-03-3) + 1-bromo-3-chlorobenzene (108-37-2) → 5-(3-chlorophenyl)thiophene-2-carbaldehyde (51081-72-2)

Guidance literature:

With palladium diacetate; potassium carbonate; tricyclohexylphosphine tetrafluoroborate; Trimethylacetic acid; In N,N-dimethyl acetamide; at 100 ℃; for 16h; regioselective reaction; Inert atmosphere;

DOI:10.1021/jo8026565

Reference yield: 48.0%

3-chlorophenylboronic acid (63503-60-6) + (E)-1-(5-bromothiophen-2-yl)-N-(4-methylpyridin-2-yl)methanimine → 5-(3-chlorophenyl)thiophene-2-carbaldehyde (51081-72-2)

Guidance literature:

(E)-1-(5-bromothiophen-2-yl)-N-(4-methylpyridin-2-yl)methanimine; With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,4-dioxane; for 0.5h; Inert atmosphere;

3-chlorophenylboronic acid; With potassium phosphate; In 1,4-dioxane; water; at 90 ℃;

DOI:10.3390/molecules24142609

Reference yield:

5-bromo-2-thiophencarboxaldehyde (4701-17-1) → 5-(3-chlorophenyl)thiophene-2-carbaldehyde (51081-72-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: acetic acid / ethanol / 80 - 85 °C

2.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane / 0.5 h / Inert atmosphere

2.2: 90 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; acetic acid; In 1,4-dioxane; ethanol; 2.1: |Suzuki Coupling / 2.2: |Suzuki Coupling;

DOI:10.3390/molecules24142609

upstream raw materials:

2-(3-chlorophenyl)thiophene

N-methyl-N-phenylformamide

thiophene-2-carbaldehyde

1-bromo-3-chlorobenzene

Downstream raw materials:

5-((5-(3-chlorophenyl)thiophen-2-yl)methylene)-2-thioxoimidazolidin-4-one