2-[4-(N-Boc)piperazin-1-yl]phenylboronic acid pinacol ester

Base Information

• Chemical Name: 2-[4-(N-Boc)piperazin-1-yl]phenylboronic acid pinacol ester
• CAS No.: 1073354-59-2
• Molecular Formula: C21H35BN2O5
• Molecular Weight: 406.324
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID80585966
• Wikidata: Q82477985
• Mol file: 1073354-59-2.mol

Synonyms:2-[4-(N-Boc)piperazin-1-yl]phenylboronic acid pinacol ester;2-[4-(tert-Butoxycarbonyl)piperazine-1-yl]phenylboronic acid

Chemical Property of 2-[4-(N-Boc)piperazin-1-yl]phenylboronic acid pinacol ester

Chemical Property:

• PSA: 51.24000
• LogP: 3.04580
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 388.2533377
• Heavy Atom Count: 28
• Complexity: 551

Purity/Quality:

98%min ^*data from raw 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=C2N3CCN(CC3)C(=O)OC(C)(C)C

Technology Process of 2-[4-(N-Boc)piperazin-1-yl]phenylboronic acid pinacol ester

There total 3 articles about 2-[4-(N-Boc)piperazin-1-yl]phenylboronic acid pinacol 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: 50.0%

4-(2-bromophenyl)piperazine-1-carboxylic acid tert-butyl ester (494773-35-2) + bis(pinacol)diborane (73183-34-3) → tert-butyl 4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperazine-1-carboxylate (1073354-59-2)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 80 ℃; for 24h; Inert atmosphere;

DOI:10.1016/j.bmcl.2020.127598

Reference yield:

2,3-dibromobenzene (583-53-9) → tert-butyl 4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperazine-1-carboxylate (1073354-59-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; potassium tert-butylate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / toluene / 24 h / 80 °C / Inert atmosphere

2: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 24 h / 80 °C / Inert atmosphere

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium tert-butylate; potassium acetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In 1,4-dioxane; toluene; 1: |Buchwald-Hartwig Coupling / 2: |Miyaura Borylation Reaction;

DOI:10.1016/j.bmcl.2020.127598

Reference yield:

1-t-Butoxycarbonylpiperazine (57260-71-6) → tert-butyl 4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperazine-1-carboxylate (1073354-59-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; potassium tert-butylate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / toluene / 24 h / 80 °C / Inert atmosphere

2: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 24 h / 80 °C / Inert atmosphere

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium tert-butylate; potassium acetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In 1,4-dioxane; toluene; 1: |Buchwald-Hartwig Coupling / 2: |Miyaura Borylation Reaction;

DOI:10.1016/j.bmcl.2020.127598

upstream raw materials:

2,3-dibromobenzene

4-(2-bromophenyl)piperazine-1-carboxylic acid tert-butyl ester

bis(pinacol)diborane

1-t-Butoxycarbonylpiperazine

Refernces