2-[3-azido-5-(azidomethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Base Information

Chemical Name:2-[3-azido-5-(azidomethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
CAS No.:1157852-36-2
Molecular Formula:C₁₃H₁₇BN₆O₂
Molecular Weight:300.128
Hs Code.:

Synonyms:2-[3-azido-5-(azidomethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

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Chemical Property of 2-[3-azido-5-(azidomethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

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Technology Process of 2-[3-azido-5-(azidomethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

There total 5 articles about 2-[3-azido-5-(azidomethyl)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: 59.3%

: 1157852-35-1
1-azido-3-(azidomethyl)-5-iodobenzene

: 73183-34-3
bis(pinacol)diborane

: 1157852-36-2
2-[3-azido-5-(azidomethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Guidance literature:: 1-azido-3-(azidomethyl)-5-iodobenzene; bis(pinacol)diborane; With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; In dimethyl sulfoxide; at 20 - 80 ℃;

With hydrogenchloride; water; In dimethyl sulfoxide;
DOI:10.1016/j.bmc.2009.01.070

Reference yield:

: 1620809-38-2
(3-ethoxycarbonyl-5-iodo)phenylboronic acid pinacol ester

: 1157852-36-2
2-[3-azido-5-(azidomethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Guidance literature:: Multi-step reaction with 4 steps

1: trimethylsilylazide; copper(l) chloride; potassium fluoride / methanol / 7 h / 20 - 70 °C

2: diisobutylaluminium hydride / hexane; tetrahydrofuran / 3 h / -78 °C / Inert atmosphere

3: diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 25 h / 20 °C / Inert atmosphere

4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / dimethyl sulfoxide / 3 h / 20 - 80 °C / Inert atmosphere

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium fluoride; trimethylsilylazide; diphenyl phosphoryl azide; potassium acetate; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; copper(l) chloride; In tetrahydrofuran; methanol; hexane; dimethyl sulfoxide; toluene; 4: |Miyaura Borylation Reaction;
DOI:10.1002/ejoc.201402516

Reference yield:

: 58313-23-8
3-iodobenzoic acid methyl ester

: 1157852-36-2
2-[3-azido-5-(azidomethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Guidance literature:: Multi-step reaction with 5 steps

1: (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine / hexane / 39 h / 20 °C / Inert atmosphere

2: trimethylsilylazide; copper(l) chloride; potassium fluoride / methanol / 7 h / 20 - 70 °C

3: diisobutylaluminium hydride / hexane; tetrahydrofuran / 3 h / -78 °C / Inert atmosphere

4: diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 25 h / 20 °C / Inert atmosphere

5: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / dimethyl sulfoxide / 3 h / 20 - 80 °C / Inert atmosphere

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium fluoride; (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; trimethylsilylazide; diphenyl phosphoryl azide; potassium acetate; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; 4,4'-di-tert-butyl-2,2'-bipyridine; copper(l) chloride; In tetrahydrofuran; methanol; hexane; dimethyl sulfoxide; toluene; 5: |Miyaura Borylation Reaction;
DOI:10.1002/ejoc.201402516