Benzenesulfonic acid, 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-, 2,2-dimethylpropyl ester

Base Information

• Chemical Name: Benzenesulfonic acid, 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-, 2,2-dimethylpropyl ester
• CAS No.: 648905-68-4
• Molecular Formula: C17H27BO5S
• Molecular Weight: 354.275
• Mol file: 648905-68-4.mol

Synonyms:4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzenesulfonic acid 2,2-dimethylpropyl ester;

Chemical Property of Benzenesulfonic acid, 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-, 2,2-dimethylpropyl ester

Chemical Property:

• Boiling Point: 443.3±28.0 °C(Predicted)
• PSA: 70.21000
• Density: 1.13±0.1 g/cm3(Predicted)
• LogP: 3.81800

Purity/Quality:

≥99% ^*data from raw suppliers

Neopentyl4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Neopentyl 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonate is an intermediate in synthesizing 5-Amino-3-(4-sulfonylphenyl)salicyclic Acid Sodium Salt (A629340), an impurity of mesalamine (M258100), which is the active metabolite of Sulfasalazine (S699084). Anti-inflammatory (gastrointestinal).

Technology Process of Benzenesulfonic acid, 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-, 2,2-dimethylpropyl ester

There total 4 articles about Benzenesulfonic acid, 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-, 2,2-dimethylpropyl ester 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: 99.0%

4-bromo-benzenesulfonic acid 2,2-dimethylpropyl ester (14248-15-8) + bis(pinacol)diborane (73183-34-3) → neopentyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonate (648905-68-4)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 90 ℃; for 6h; Schlenk technique; Inert atmosphere;

DOI:10.1039/d0cc02486d

Reference yield:

4-bromobenzenesulfonyl chloride (98-58-8) → neopentyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonate (648905-68-4)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / dichloromethane / 12.5 h / 0 - 20 °C

2: bis-triphenylphosphine-palladium(II) chloride; potassium acetate / 1,4-dioxane / 6 h / 100 °C / Inert atmosphere

With pyridine; bis-triphenylphosphine-palladium(II) chloride; potassium acetate; In 1,4-dioxane; dichloromethane;

DOI:10.1021/ma402362w

Reference yield:

2,2-dimethyl-propanol-1 (75-84-3) → neopentyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonate (648905-68-4)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / 1,2-dichloro-ethane / 12 h / 20 °C / Cooling with ice; Inert atmosphere

2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 12 h / 100 °C / Inert atmosphere

With pyridine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; 1,2-dichloro-ethane;

DOI:10.1016/j.dyepig.2020.108586

upstream raw materials:

4-bromo-benzenesulfonic acid 2,2-dimethylpropyl ester

bis(pinacol)diborane

bromobenzene

4-bromobenzenesulfonyl chloride

Downstream raw materials:

4-(5-bromofuran-2-yl)benzenesulfonic acid 2,2-dimethylpropyl ester

4-(5-bromothiophen-2-yl)benzenesulfonic acid 2,2-dimethylpropyl ester

4-(5-(4-(dimethylamino)phenyl)thiophen-2-yl)benzenesulfonic acid 2,2-dimethylpropyl ester

4-(5-(4-(dimethylamino)phenyl)furan-2-yl)benzenesulfonic acid 2,2-dimethylpropyl ester