5-(trimethylsilyl)thiophene-2-carbaldehyde

Base Information

• Chemical Name: 5-(trimethylsilyl)thiophene-2-carbaldehyde
• CAS No.: 13960-01-5
• Molecular Formula: C₈H₁₂OSSi
• Molecular Weight: 184.334

Synonyms:5-(trimethylsilyl)thiophene-2-carbaldehyde

Chemical Property of 5-(trimethylsilyl)thiophene-2-carbaldehyde

Chemical Property:

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Technology Process of 5-(trimethylsilyl)thiophene-2-carbaldehyde

There total 2 articles about 5-(trimethylsilyl)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: 57.0%

2-bromo-5-trimethylsilylthiophene (18246-28-1) + Trimethyl borate (121-43-7,63156-11-6) → 2-(trimethylsilyl)thiophene (18245-28-8) + 5-(trimethylsilyl)thiophene-2-carbaldehyde (13960-01-5) + 2-(trimethylsilyl)-5-thienyl boronic acid (138983-68-3)

Guidance literature:

With aluminium; In N,N-dimethyl-formamide; byproducts: Al(3+); Electrolysis; electrolysis carried out in a single-compartment cell at room temp., starting materials dissolved in DMF containing KBr or n-Bu4NBr, solvent andexcess B(OCH3)3 evaporated under vacuum, medium hydrolysed at 0° C with an HCl or H2SO4 soln.; extraction with Et2O (3 x 20 ml if the solvent evaporated or 3 x 60 ml otherwise), dried over sodium or magnesium sulfate and concentrated undervacuum, side product phenol formation avoided by work-up under inert at mosphere, recrystallized in CH2Cl2;

DOI:10.1039/b200744b

Reference yield:

3-bromo-2-thiophenecarboxaldehyde (930-96-1) → 5-(trimethylsilyl)thiophene-2-carbaldehyde (13960-01-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: toluene / 16 h / Dean-Stark; Reflux; Inert atmosphere

2.1: lithium diisopropyl amide / hexane; tetrahydrofuran / 0.92 h / 0 °C / Inert atmosphere

2.2: 1 h / -78 - 20 °C / Inert atmosphere

3.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

3.2: 0.25 h / -78 - 20 °C / Inert atmosphere

4.1: copper(I) thiophene-2-carboxylate / 1-methyl-pyrrolidin-2-one / 60 h / 60 °C / Inert atmosphere

4.2: 20 °C / Inert atmosphere

With n-butyllithium; copper(I) thiophene-2-carboxylate; lithium diisopropyl amide; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; hexane; toluene;

DOI:10.1055/s-0033-1340667

Reference yield: 69.0%

5-(trimethylsilyl)thiophene-2-carbaldehyde (13960-01-5) + 2-amino-phenol (95-55-6) → 2-[(5-trimethylsilyl-2-thienyl)methyleneamino]phenol

Guidance literature:

In ethanol; at 20 ℃; for 10h;

DOI:10.1016/j.crci.2019.10.002

upstream raw materials:

2-bromo-5-trimethylsilylthiophene

Trimethyl borate

3-bromo-2-thiophenecarboxaldehyde

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