tert-butyl 6-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-ylcarbaMate

Base Information

• Chemical Name: tert-butyl 6-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-ylcarbaMate
• CAS No.: 1312611-41-8
• Molecular Formula: C₂₁H₂₈BNO₄
• Molecular Weight: 369.269
• Mol file: 1312611-41-8.mol

Synonyms:tert-butyl 6-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-ylcarbaMate;(6-((tert-Butoxycarbonyl)amino)naphthalen-2-yl)boronic acid pinacol ester

Chemical Property of tert-butyl 6-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-ylcarbaMate

Chemical Property:

• PSA: 56.79000
• LogP: 4.55900
• Storage Temp.: 2-8°C

Purity/Quality:

97% ^*data from raw suppliers

tert-butyl6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-ylcarbamate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
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MSDS Files:

SDS file from LookChem

Useful:

Technology Process of tert-butyl 6-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-ylcarbaMate

There total 4 articles about tert-butyl 6-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-ylcarbaMate 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: 83.0%

6-bromo-2-N-tert-butoxycarbonylaminonaphthalene (869114-68-1) + bis(pinacol)diborane (73183-34-3) → tert-butyl [6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-naphthalen-2-yl]carbamate (1312611-41-8)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; In 1,2-dichloro-ethane; at 80 ℃; for 18h;

DOI:10.1021/acs.joc.9b01844

Reference yield:

6-bromo-2-naphthoic acid (5773-80-8) → tert-butyl [6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-naphthalen-2-yl]carbamate (1312611-41-8)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine; diphenyl phosphoryl azide / 100 °C

2: potassium acetate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane / 8 h / 110 °C / Inert atmosphere

With diphenyl phosphoryl azide; potassium acetate; triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,4-dioxane;

Reference yield:

6-Bromonaphthalen-2-amine (7499-66-3) → tert-butyl [6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-naphthalen-2-yl]carbamate (1312611-41-8)

Guidance literature:

Multi-step reaction with 2 steps

1: acetic acid / 144 h / Inert atmosphere

2: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium acetate / 1,4-dioxane / 72 h / 98 °C / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium acetate; acetic acid; In 1,4-dioxane;

DOI:10.1002/ejoc.201700970

upstream raw materials:

6-bromo-2-N-tert-butoxycarbonylaminonaphthalene

bis(pinacol)diborane

6-bromo-2-naphthoic acid

6-Bromonaphthalen-2-amine

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