N-[2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethyl]methanesulfonamide

Base Information

• Chemical Name: N-[2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethyl]methanesulfonamide
• CAS No.: 375345-99-6
• Molecular Formula: C₁₅H₂₄BNO₄S
• Molecular Weight: 325.237
• DSSTox Substance ID: DTXSID80467056
• Mol file: 375345-99-6.mol

Synonyms:375345-99-6;N-[2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethyl]methanesulfonamide;N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenethyl)methanesulfonamide;N-{2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethyl}methanesulfonamide;SCHEMBL1870103;DTXSID80467056;FCELYMGZBFPPSM-UHFFFAOYSA-N

Chemical Property of N-[2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethyl]methanesulfonamide

Chemical Property:

• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 325.1519096
• Heavy Atom Count: 22
• Complexity: 462

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC=C(C=C2)CCNS(=O)(=O)C

Technology Process of N-[2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethyl]methanesulfonamide

There total 7 articles about N-[2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethyl]methanesulfonamide 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: 91.4%

N-(t-butoxycarbonyl)-N-(methylsulfonyl)-N-(2-(4-(4,4,5,5-tetramethyl(1,3,2-dioxaborolan-2-yl))phenyl)ethyl)amine (353235-95-7) → N-[2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl]ethyl]methanesulfonamide (375345-99-6)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 18h;

Reference yield: 67.2%

N-(2-(4-iodophenyl)ethyl)-N-(methylsulfonyl)amine (353235-93-5) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → N-[2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl]ethyl]methanesulfonamide (375345-99-6)

Guidance literature:

N-(2-(4-iodophenyl)ethyl)-N-(methylsulfonyl)amine; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane; With triethylamine; In acetonitrile; at 14 - 30 ℃; for 4.25h; Inert atmosphere;

With palladium; In acetonitrile; at 75 ℃; for 24h; Inert atmosphere;

DOI:10.1021/op060180i

Reference yield:

N-(2-(4-iodophenyl)ethyl)-N-(methylsulfonyl)amine (353235-93-5) → N-[2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl]ethyl]methanesulfonamide (375345-99-6)

Guidance literature:

Multi-step reaction with 3 steps

1: dmap / dichloromethane / 20 °C

2: triethylamine / 1,1'-bis(diphenylphosphino) ferrocene-dichloropalladium (II)-CH₂Cl₂ complex / acetonitrile / 8 h / 70 - 74 °C

3: trifluoroacetic acid / dichloromethane / 18 h / 20 °C

With dmap; triethylamine; trifluoroacetic acid; 1,1'-bis(diphenylphosphino) ferrocene-dichloropalladium (II)-CH₂Cl₂ complex; In dichloromethane; acetonitrile;

upstream raw materials:

N-(t-butoxycarbonyl)-N-(methylsulfonyl)-N-(2-(4-(4,4,5,5-tetramethyl(1,3,2-dioxaborolan-2-yl))phenyl)ethyl)amine

N-(2-(4-iodophenyl)ethyl)-N-(methylsulfonyl)amine

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

N-(t-butoxycarbonyl)-N-(2-(4-iodophenyl)ethyl)-N-(methylsulfonyl)amine

Downstream raw materials:

[4-[2-[(methylsulfonyl)amino]ethyl]phenyl]boronic acid

{(2R)-2-[4-(4-{2-[(methylsulfonyl)amino]ethyl}phenyl)phenyl]-propyl}[(methylethyl)sulfonyl]amine

N,N'-([1,1'-biphenyl]-4,4'-diyldi-2,1-ethanediyl)-bis-methanesulfonamide