3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-YL)benzenesulfonamide

Base Information

• Chemical Name: 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-YL)benzenesulfonamide
• CAS No.: 486422-08-6
• Molecular Formula: C12H18BNO4S
• Molecular Weight: 283.156
• Hs Code.: 2935009090
• European Community (EC) Number: 878-769-4
• DSSTox Substance ID: DTXSID50585973
• Wikidata: Q82477990
• Mol file: 486422-08-6.mol

Synonyms:486422-08-6;3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZENESULFONAMIDE;BENZENESULFONAMIDE-3-BORONIC ACID PINACOL ESTER;3-Boronobenzenesulfonamide, pinacol ester;BENZENESULFONAMIDE, 3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-;MFCD07781217;3-Sulfamoylphenylboronic Acid Pinacol Ester;SCHEMBL182781;(3-SULFAMOYLPHENYL)BORONIC ACID PINACOL ESTER;OSM-S-151;DTXSID50585973;OHKKUZJVWWPUNY-UHFFFAOYSA-N;AKOS022183908;AB42590;DS-17402;SY021257;CS-0036799;EN300-206714;benzenesulfon-amide-3-boronic acid pinacol ester;A871898;Z2027931957;benzenesulfonamide-3-boronic acid pinacol ester, AldrichCPR;3-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzene-1-sulfonamide;3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzenesulfonamide;3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-benzenesulfonamide;3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzene-1-sulfonamide

Chemical Property of 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-YL)benzenesulfonamide

Chemical Property:

• Boiling Point: 447.1±47.0 °C(Predicted)
• PKA: 10.04±0.60(Predicted)
• PSA: 87.00000
• Density: 1.24±0.1 g/cm3(Predicted)
• LogP: 2.41430
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 283.1049594
• Heavy Atom Count: 19
• Complexity: 427

Purity/Quality:

98%min ^*data from raw suppliers

3-Boronobenzenesulfonamide,pinacolester ^*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(=CC=C2)S(=O)(=O)N

Technology Process of 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-YL)benzenesulfonamide

There total 3 articles about 3-(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: 89.0%

3-bromobenzenesulfonamide (89599-01-9) + bis(pinacol)diborane (73183-34-3) → 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene-1-sulfonamide (486422-08-6)

Guidance literature:

With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate; In 1,4-dioxane; at 100 ℃; for 24h; Inert atmosphere;

Reference yield:

4,4,4',4',5,5,5'-heptamethyl-2,2'-bi(1,3,2-dioxaborolane) + 3-bromobenzenesulfonamide (89599-01-9) → 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene-1-sulfonamide (486422-08-6)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; water; Inert atmosphere; Reflux;

DOI:10.1016/j.ejmech.2016.11.004

Reference yield:

3-Bromobenzenesulfonyl chloride (2905-24-0) → 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene-1-sulfonamide (486422-08-6)

Guidance literature:

Multi-step reaction with 2 steps

1: ammonium hydroxide / dichloromethane; water / 6.5 h / 20 °C / Cooling with ice

2: potassium acetate; palladium bis[bis(diphenylphosphino)ferrocene] dichloride / 1,4-dioxane / 24 h / 100 °C / Inert atmosphere

With ammonium hydroxide; palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate; In 1,4-dioxane; dichloromethane; water;

upstream raw materials:

3-bromobenzenesulfonamide

bis(pinacol)diborane

3-Bromobenzenesulfonyl chloride

Downstream raw materials:

tert-butyl ((2S,3R)-3-(tert-butoxy)-1-oxo-1-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamido)butan-2-yl)carbamate

C₁₈H₁₉N₅O₄S

C₁₈H₂₀N₆O₄S

C₁₈H₁₈ClN₅O₄S

Refernces

• 1、 Abdelsamie, Ahmed S.,Salah, Mohamed,Siebenbürger, Lorenz,Hamed, Mostafa M.,B?rger, Carsten,van Koppen, Chris J.,Frotscher, Martin,Hartmann, Rolf W.. "Development of potential preclinical candidates with promising in vitro ADME profile for the inhibition of type 1 and type 2 17β-Hydroxysteroid dehydrogenases: Design, synthesis, and biological evaluation". . p. 93 - 107. Retrieved 2019/06/08.
• 2、 -. "NOVEL N-ACYL-ARYLSULFONAMIDE DERIVATIVES AS AMINOACYL-TRNA SYNTHETASE INHIBITORS". Page/Page column 35. . Retrieved 2016/09/22.