N-(2-Hydroxyethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)benzamide

Base Information

• Chemical Name: N-(2-Hydroxyethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)benzamide
• CAS No.: 1073353-51-1
• Molecular Formula: C₁₅H₂₂BNO₄
• Molecular Weight: 291.155
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID80592130
• Wikidata: Q82486066
• Mol file: 1073353-51-1.mol

Synonyms:1073353-51-1;4-(2-HYDROXYETHYLCARBAMOYL)PHENYLBORONIC ACID, PINACOL ESTER;N-(2-HYDROXYETHYL)-4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZAMIDE;4-(2-Hydroxyethylcarbamoyl)phenylboronic acid pinacol ester;N-[2-HYDROXYETHYL]BENZAMIDE-4-BORONIC ACID, PINACOL ESTER;SCHEMBL15648726;DTXSID80592130;LOKVHTSZMDAUEL-UHFFFAOYSA-N;YSB35351;MFCD06795648;AKOS015960093;AB29166;BS-25173;DA-15834;CS-0176491;F75629;J-001793;N-(2-Hydroxyethyl)-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide;N-[2-hydroxyethyl]benzamide-4-boronic acid, pinacol ester, AldrichCPR

Chemical Property of N-(2-Hydroxyethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)benzamide

Chemical Property:

• PSA: 67.79000
• LogP: 1.09880
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 291.1641883
• Heavy Atom Count: 21
• Complexity: 362

Purity/Quality:

98%min ^*data from raw suppliers

4-(2-Hydroxyethylcarbamoyl)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)C(=O)NCCO
• Uses: 4-(2-Hydroxyethylcarbamoyl)phenylboronic acid, pinacol ester

Technology Process of N-(2-Hydroxyethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)benzamide

There total 2 articles about N-(2-Hydroxyethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)benzamide 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:

N-(2-hydroxyethyl)-p-bromobenzamide (57728-67-3) + bis(pinacol)diborane (73183-34-3) → N-(2-hydroxyethyl)benzamide-4-boronic acid pinacol ester (1073353-51-1)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In N,N-dimethyl-formamide; at 100 ℃; for 3h; Inert atmosphere;

DOI:10.1021/acs.jmedchem.0c02118

Reference yield:

2-(4-bromobenzamido)ethyl 4-bromobenzoate (951885-58-8) → N-(2-hydroxyethyl)benzamide-4-boronic acid pinacol ester (1073353-51-1)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium hydroxide / tetrahydrofuran; water / 16 h / 60 °C

2: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 3 h / 100 °C / Inert atmosphere

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; potassium hydroxide; In tetrahydrofuran; water; N,N-dimethyl-formamide; 2: |Miyaura Borylation Reaction;

DOI:10.1021/acs.jmedchem.0c02118

Reference yield:

N-(2-hydroxyethyl)benzamide-4-boronic acid pinacol ester (1073353-51-1) + 4-bromo-7-azaindole (348640-06-2) → N-(2-hydroxyethyl)-4-(1H-pyrrolo[2,3-b]pyridin-4-yl)-benzamide

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydrogencarbonate; In water; N,N-dimethyl-formamide; at 100 ℃; for 18h; Inert atmosphere;

DOI:10.1021/acs.jmedchem.0c02118

upstream raw materials:

2-(4-bromobenzamido)ethyl 4-bromobenzoate

N-(2-hydroxyethyl)-p-bromobenzamide

bis(pinacol)diborane

Refernces