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

Base Information

• Chemical Name: 5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carbaldehyde
• CAS No.: 1040281-83-1
• Molecular Formula: C11H15BO3S
• Molecular Weight: 238.115
• Hs Code.: 2934999090
• Mol file: 1040281-83-1.mol

Synonyms:5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carbaldehyde;5-Formyl-2-thiopheneboronic acid pinacol ester;2-(4,4,5,5-tetramethy-1,3,2-dioxaborolan-2-yl)-thiophene-5-carbaldehyde;5-Formylthiophene-2-boronicacid,pinacolester

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

Chemical Property:

• Melting Point: 66.0 to 70.0 °C
• Boiling Point: 359.1±27.0 °C(Predicted)
• PSA: 63.77000
• Density: 1.14±0.1 g/cm3(Predicted)
• LogP: 1.85980
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C

Purity/Quality:

97% ^*data from raw suppliers

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carbaldehyde ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37

MSDS Files:

SDS file from LookChem

Useful:

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

There total 3 articles about 5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)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: 92.2%

2,3-dimethyl-2,3-butane diol (76-09-5) + (5-formylthiophen-2-yl)boronic acid → 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carboxaldehyde (1040281-83-1)

Guidance literature:

In toluene; at 100 ℃;

DOI:10.1002/chem.201500835

Reference yield: 88.9%

5-bromo-2-thiophencarboxaldehyde (4701-17-1) + bis(pinacol)diborane (73183-34-3) → 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carboxaldehyde (1040281-83-1)

Guidance literature:

With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate; In 1,4-dioxane; at 80 ℃; for 6h; Inert atmosphere;

DOI:10.1016/j.tet.2012.08.027

Reference yield:

2-(2-thienyl)-1,3-dioxolane (58268-08-9) → 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carboxaldehyde (1040281-83-1)

Guidance literature:

Multi-step reaction with 2 steps

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

1.2: 1 h / 20 °C / Inert atmosphere

2.1: magnesium sulfate / tetrahydrofuran / 24 h / 20 °C

With n-butyllithium; magnesium sulfate; In tetrahydrofuran; hexane;

DOI:10.1002/chem.201402093

upstream raw materials:

5-bromo-2-thiophencarboxaldehyde

bis(pinacol)diborane

2-(2-thienyl)-1,3-dioxolane

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

Downstream raw materials:

5′-(4-(diphenylamino)phenyl)(2,2′-bithiophene)-5-carboxaldehyde

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