5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2yl)benzo[d]oxazol-2-amine

Base Information

• Chemical Name: 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2yl)benzo[d]oxazol-2-amine
• CAS No.: 1224844-66-9
• Molecular Formula: C13H17BN2O3
• Molecular Weight: 260.101
• Hs Code.: 2934999090
• Mol file: 1224844-66-9.mol

Synonyms:5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2yl)benzo[d]oxazol-2-amine;2-aminobenzo[d]oxazol-5-ylboronic acid pinacol ester

Chemical Property of 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2yl)benzo[d]oxazol-2-amine

Chemical Property:

• Boiling Point: 411.7±37.0 °C(Predicted)
• PKA: 1.75±0.10(Predicted)
• PSA: 71.24000
• Density: 1.19±0.1 g/cm3(Predicted)
• LogP: 1.63930
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C

Purity/Quality:

98% ^*data from raw suppliers

2-Aminobenzo[d]oxazol-5-ylboronicAcidPinacolEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 2-Aminobenzo[d]oxazol-5-ylboronic acid pinacol ester is a useful intermediate for the development of small-molecular inhibitors (mTOR inhibitors) that targets cancer.

Technology Process of 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2yl)benzo[d]oxazol-2-amine

There total 5 articles about 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2yl)benzo[d]oxazol-2-amine 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: 89.5%

bis(pinacol)diborane (73183-34-3) + 5-bromo-1,3-benzoxazol-2-amine (64037-07-6) → 5-( 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazol-2-amine (1224844-66-9)

Guidance literature:

With dichloro[1,1'-bis(diphenylphosphino)ferrocene]palladium cesium chloride; potassium acetate; In 1,4-dioxane; for 3h; Inert atmosphere; Reflux;

Reference yield:

2-amino-4-bromo-phenol (40925-68-6) → 5-( 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazol-2-amine (1224844-66-9)

Guidance literature:

Multi-step reaction with 2 steps

1: methanol / 15 h / 18 - 37 °C / Large scale

2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate / 1,4-dioxane / 18 - 103 °C / Inert atmosphere; Reflux; Large scale

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; In 1,4-dioxane; methanol;

Reference yield:

4-bromo-phenol (106-41-2) → 5-( 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazol-2-amine (1224844-66-9)

Guidance literature:

Multi-step reaction with 4 steps

1: nitric acid; sulfuric acid / 0.5 h / 0 °C

2: tin(II) chloride dihdyrate / ethanol / 2 h / 75 °C

3: methanol / 35 °C

4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 5 h / 80 °C

With methanol; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tin(II) chloride dihdyrate; sulfuric acid; nitric acid; potassium acetate; In 1,4-dioxane; ethanol;

upstream raw materials:

bis(pinacol)diborane

5-bromo-1,3-benzoxazol-2-amine

2-amino-4-bromo-phenol

4-bromo-phenol

Downstream raw materials:

2-amino-benzooxazole-5-boronic acid hydrochloride

2-(4-(8-(2-aminobenzo[d]oxazol-5-yl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)phenyl)-2-methylpropanenitril

(6-(2-aminobenzo[d]oxazol-5-yl)imidazo[1,2-a]pyridin-3-yl)(morpholino)methanone

INK128

Refernces

• 1、 -. "PI3Kalpha selective inhibitor and preparation method and application thereof". Paragraph 0078-0080. . Retrieved 2021/08/06.
• 2、 -. "TRICYCLIC PI3K INHIBITOR COMPOUNDS AND METHODS OF USE". . . Retrieved 2018/03/25.