2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-3-carbaldehyde

Base Information

• Chemical Name: 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-3-carbaldehyde
• CAS No.: 632325-55-4
• Molecular Formula: C11H15BO3S
• Molecular Weight: 238.11
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID60473579
• Nikkaji Number: J1.983.839K
• Wikidata: Q72479495
• Mol file: 632325-55-4.mol

Synonyms:632325-55-4;2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-3-carbaldehyde;3-Formylthiophene-2-boronic acid pinacol ester;DTXSID60473579;MFCD09952063;AKOS015950003;BS-29069;CS-0174502;D71423;EN300-335942;J-505877;2-(TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)THIOPHENE-3-CARBALDEHYDE

Chemical Property of 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-3-carbaldehyde

Chemical Property:

• PSA: 63.77000
• LogP: 1.85980
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 238.0834957
• Heavy Atom Count: 16
• Complexity: 277

Purity/Quality:

97% ^*data from raw suppliers

3-Formylthiophene-2-boronicAcidPinacolEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=C(C=CS2)C=O

Technology Process of 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-3-carbaldehyde

There total 2 articles about 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-3-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: 97.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + 3-formylthiophene-2-boronic acid (17303-83-2) → 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-3-carbaldehyde (632325-55-4)

Guidance literature:

In diethyl ether; at 20 ℃; for 24h;

DOI:10.1039/d1tc00710f

Reference yield:

2-bromothiophene-3-carbaldehyde (1860-99-7) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-3-carbaldehyde (632325-55-4)

Guidance literature:

With bis(tri-t-butylphosphine)palladium⁽⁰⁾; triethylamine; In tetrahydrofuran; at 40 ℃; for 3h;

DOI:10.1021/jo034919n

Reference yield:

2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-3-carbaldehyde (632325-55-4) → 4-(3'-(((tetrahydro-2H-pyran-2-yl)oxy)methyl)-5''-(3,4,5-tris(dodecyloxy)phenyl)-[2,2':5',2''-terthiophen]-5-yl)phthalonitril

Guidance literature:

Multi-step reaction with 5 steps

1: sodium tetrahydroborate / tetrahydrofuran / 24 h / 0 - 20 °C / Inert atmosphere

2: sodium hydrogencarbonate; pyridinium p-toluenesulfonate / dichloromethane / 24 h / 20 °C / Inert atmosphere

3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / water; tetrahydrofuran / 24 h / 90 °C / Inert atmosphere

4: N-Bromosuccinimide / tetrahydrofuran / 72 h / 20 °C

5: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / water; tetrahydrofuran / 24 h / 90 °C / Inert atmosphere

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium tetrahydroborate; N-Bromosuccinimide; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; potassium carbonate; In tetrahydrofuran; dichloromethane; water;

DOI:10.1039/d1tc00710f

upstream raw materials:

2-bromothiophene-3-carbaldehyde

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

2,3-dimethyl-2,3-butane diol

3-formylthiophene-2-boronic acid