2-(4-(2-Chloroethoxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Base Information

• Chemical Name: 2-(4-(2-Chloroethoxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS No.: 1256359-01-9
• Molecular Formula: C₁₄H₂₀BClO₃
• Molecular Weight: 282.575
• DSSTox Substance ID: DTXSID00681939
• Wikidata: Q82606127
• Mol file: 1256359-01-9.mol

Synonyms:1256359-01-9;2-(4-(2-Chloroethoxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-[4-(2-chloroethoxy)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;4-(2-Chloroethoxy)phenylboronic acid, pinacol ester;2-[4-(2-CHLORO-ETHOXY)-PHENYL]-4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLANE;DTXSID00681939;AMY27308;MFCD09746199;AKOS015850755;AS-3211;CS-0111598;4-(2-Chloroethoxy)phenylboronic acid,pinacol ester;2-[4-(2-Chloroethoxy)phenyl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

Chemical Property of 2-(4-(2-Chloroethoxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property:

• PSA: 27.69000
• LogP: 2.60340
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 282.1194024
• Heavy Atom Count: 19
• Complexity: 285

Purity/Quality:

97% ^*data from raw suppliers

4-(2-Chloroethoxy)phenylboronicacid,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=C(C=C2)OCCCl

Technology Process of 2-(4-(2-Chloroethoxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

There total 2 articles about 2-(4-(2-Chloroethoxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 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: 45.0%

1-bromo-4-(2-chloroethoxy)benzene (55162-34-0) + bis(pinacol)diborane (73183-34-3) → 2-(4-(2-chloroethoxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1256359-01-9)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 90 ℃; for 2h; Inert atmosphere;

Reference yield:

4-bromo-phenol (106-41-2) → 2-(4-(2-chloroethoxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1256359-01-9)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium carbonate / butanone / 16 h / 90 °C

2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 2 h / 90 °C / Inert atmosphere

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; potassium carbonate; In 1,4-dioxane; butanone;

Reference yield:

2-(4-(2-chloroethoxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1256359-01-9) → (E)-methyl 5-(4-(2-(3-azabicyclo[3.1.0]hexan-3-yl)ethoxy)phenyl)-4-phenyl-5-(4-(pivaloyloxy)phenyl)pent-4-enoate

Guidance literature:

Multi-step reaction with 2 steps

1: bis(benzonitrile)palladium(II) dichloride; caesium carbonate / water; N,N-dimethyl-formamide / 12 h / 45 °C

2: sodium iodide; triethylamine / N,N-dimethyl-formamide / 80 °C

With bis(benzonitrile)palladium(II) dichloride; caesium carbonate; triethylamine; sodium iodide; In water; N,N-dimethyl-formamide;

DOI:10.1021/acs.jmedchem.6b01204

upstream raw materials:

1-bromo-4-(2-chloroethoxy)benzene

bis(pinacol)diborane

4-bromo-phenol

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