N,N-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide

Base Information

• Chemical Name: N,N-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide
• CAS No.: 486422-04-2
• Molecular Formula: C14H22BNO4S
• Molecular Weight: 311.21
• Hs Code.: 2935009090
• DSSTox Substance ID: DTXSID50397619
• Wikidata: Q82199123
• Mol file: 486422-04-2.mol

Synonyms:486422-04-2;4-(N,N-DIMETHYLAMINOSULFONYL)PHENYLBORONIC ACID PINACOL ESTER;N,N-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide;N,N-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene-1-sulfonamide;SCHEMBL183232;DTXSID50397619;CTBRPVYZBIZUDQ-UHFFFAOYSA-N;STR09906;(4-(N,N-DIMETHYLSULFAMOYL)PHENYL)BORONIC ACID PINACOL ESTER;MFCD03425962;AKOS022182191;AB14727;CS-0046873;EN300-7374681;A871901;4-(N,N-Dimethylaminosulfonyl)phenylboronic acid, pinacol ester;4-(N,N-Dimethylaminosulphonyl)benzeneboronic acid pinacol ester;4-(N,N-Dimethylsulfamoyl)benzene-boronic acid, pinacol ester;N,N-dimethyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzene-1-sulfonamide;N,N-dimethyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzenesulfonamide;N,N-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene-sulfonamide

Chemical Property of N,N-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide

Chemical Property:

• Boiling Point: 415.2±47.0 °C(Predicted)
• PKA: -4.88±0.70(Predicted)
• PSA: 64.22000
• Density: 1.18±0.1 g/cm3(Predicted)
• LogP: 2.31690
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), DMSO (Slightly)
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 311.1362595
• Heavy Atom Count: 21
• Complexity: 460

Purity/Quality:

97% ^*data from raw suppliers

4-(N,N-Dimethylaminosulfonyl)phenylboronicacidpinacolester ^*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=CC=C(C=C2)S(=O)(=O)N(C)C

Technology Process of N,N-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide

There total 4 articles about N,N-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide 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: 77.0%

4-bromo-N,N-dimethylbenzenesulfonamide (707-60-8) + bis(pinacol)diborane (73183-34-3) → N,N-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene-1-sulfonamide (486422-04-2)

Guidance literature:

4-bromo-N,N-dimethylbenzenesulfonamide; bis(pinacol)diborane; With potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In dimethyl sulfoxide; at 20 - 90 ℃; for 8h;

With water; In dimethyl sulfoxide;

Reference yield: 40.2%

→ N,N-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene-1-sulfonamide (486422-04-2)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; In 1,4-dioxane; at 80 ℃; for 12h; Sealed tube; Inert atmosphere;

Reference yield:

4-bromobenzenesulfonyl chloride (98-58-8) → N,N-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene-1-sulfonamide (486422-04-2)

Guidance literature:

Multi-step reaction with 2 steps

1: water; tetrahydrofuran / 1.08 h / 5 - 20 °C

2: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane / 16 h / 80 °C / Inert atmosphere

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; In tetrahydrofuran; 1,4-dioxane; water;

upstream raw materials:

4-bromo-N,N-dimethylbenzenesulfonamide

bis(pinacol)diborane

4-bromobenzenesulfonyl chloride

p-Iodobenzenesulfonyl chloride

Downstream raw materials:

N,N-dimethyl-4-[3-(1-quinolin-6-ylcyclopropyl)imidazo[1,2-a]pyrimidin-6-yl]benzenesulfonamide

6-{4-[(dimethylamino)sulfonyl]phenyl}-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-3-methyl-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

8-(4-(N,N-dimethylsulfamoyl)phenyl)-1,6-naphthyridine-2-carboxamide

C₈H₁₀⁽¹⁸⁾FNO₂S