4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[c][1,2,5]thiadiazole

Base Information

• Chemical Name: 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[c][1,2,5]thiadiazole
• CAS No.: 1088118-97-1
• Molecular Formula: C₁₂H₁₅BN₂O₂S
• Molecular Weight: 262.14
• Mol file: 1088118-97-1.mol

Synonyms:4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[c][1,2,5]thiadiazole

Chemical Property of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[c][1,2,5]thiadiazole

Chemical Property:

• Boiling Point: 366.3±15.0 °C(Predicted)
• Density: 1.22±0.1 g/cm3(Predicted)

Purity/Quality:

95% ^*data from raw suppliers

4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzo[1,2,5]thiadiazole 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[c][1,2,5]thiadiazole

There total 2 articles about 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[c][1,2,5]thiadiazole 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: 70.0%

4-Bromo-benzo[1,2,5]thiadiazole (22034-13-5) + bis(pinacol)diborane (73183-34-3) → 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[c][1,2,5]thiadiazole (1088118-97-1)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 110 ℃; for 24h; Schlenk technique;

DOI:10.1002/anie.201810326

Reference yield:

benzo[1,2,5]thiadiazole (273-13-2,22706-22-5) → 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[c][1,2,5]thiadiazole (1088118-97-1)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogen bromide; bromine / 3 h / Reflux

2: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 24 h / 110 °C / Schlenk technique

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; hydrogen bromide; bromine; potassium acetate; In 1,4-dioxane;

DOI:10.1002/anie.201810326

Reference yield: 80.0%

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[c][1,2,5]thiadiazole (1088118-97-1) + N,N-bis(4-bromophenyl)aniline (81090-53-1) → C30H19N5S2

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; In tetrahydrofuran; water; at 80 ℃;

DOI:10.1002/anie.201810326

upstream raw materials:

4-Bromo-benzo[1,2,5]thiadiazole

bis(pinacol)diborane

benzo[1,2,5]thiadiazole

Downstream raw materials:

6-phenyl-3,9-di(benzothiadiazole-4-yl)-5H-dibenzo[d,f][1,3]diazepine