2H-1,4-Benzoxazine, 3,4-dihydro-7-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-

Base Information

• Chemical Name: 2H-1,4-Benzoxazine, 3,4-dihydro-7-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-
• CAS No.: 1361110-64-6
• Molecular Formula: C14H20BNO3
• Molecular Weight: 261.1245
• Hs Code.: 2934999090
• Mol file: 1361110-64-6.mol

Synonyms:2H-1,4-Benzoxazine, 3,4-dihydro-7-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-;7-(4,4,5,5-TetraMethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine;7-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,4-dihydro-2H-benzo[1,4]oxazine

Chemical Property of 2H-1,4-Benzoxazine, 3,4-dihydro-7-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-

Chemical Property:

• Boiling Point: 390.3±42.0 °C(Predicted)
• PKA: 3.93±0.20(Predicted)
• PSA: 39.72000
• Density: 1.12±0.1 g/cm3(Predicted)
• LogP: 1.92810
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C

Purity/Quality:

NLT 98% ^*data from raw suppliers

7-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 3,4-Dihydro-2H-1,4-benzoxazine-7-boronic acid pinacol ester is a useful intermediate for the synthesis of naphthamides which functions as VEGFR-2 kinase inhibitors for cancer treatment.

Technology Process of 2H-1,4-Benzoxazine, 3,4-dihydro-7-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-

There total 4 articles about 2H-1,4-Benzoxazine, 3,4-dihydro-7-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)- 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: 75.0%

7-bromo-3,4-dihydro-2H-benzo[b][1,4]oxazine (105679-22-9) + bis(pinacol)diborane (73183-34-3) → 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine (1361110-64-6)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 110 ℃; for 16h; Sealed tube;

DOI:10.1021/jm201561r

Reference yield:

5-bromo-2-nitrophenol (27684-84-0) → 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine (1361110-64-6)

Guidance literature:

Multi-step reaction with 4 steps

1: iron; ammonium chloride / ethanol; water / 0.5 h / 50 - 70 °C

2: caesium carbonate / acetonitrile / 20 °C

3: borane-THF / tetrahydrofuran / 1 h / Inert atmosphere; Reflux

4: 1,1'-bis-(diphenylphosphino)ferrocene; potassium acetate / 1,4-dioxane / 4 h / 110 °C / Inert atmosphere

With 1,1'-bis-(diphenylphosphino)ferrocene; borane-THF; potassium acetate; iron; ammonium chloride; caesium carbonate; In tetrahydrofuran; 1,4-dioxane; ethanol; water; acetonitrile;

DOI:10.1021/ml5000417

Reference yield:

2-amino-5-bromophenol (38191-34-3) → 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine (1361110-64-6)

Guidance literature:

Multi-step reaction with 3 steps

1: caesium carbonate / acetonitrile / 20 °C

2: borane-THF / tetrahydrofuran / 1 h / Inert atmosphere; Reflux

3: 1,1'-bis-(diphenylphosphino)ferrocene; potassium acetate / 1,4-dioxane / 4 h / 110 °C / Inert atmosphere

With 1,1'-bis-(diphenylphosphino)ferrocene; borane-THF; potassium acetate; caesium carbonate; In tetrahydrofuran; 1,4-dioxane; acetonitrile;

DOI:10.1021/ml5000417

upstream raw materials:

7-bromo-3,4-dihydro-2H-benzo[b][1,4]oxazine

bis(pinacol)diborane

5-bromo-2-nitrophenol

2-amino-5-bromophenol

Downstream raw materials:

N-phenyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-benzo[b][1,4]oxazine-4(3H)-carboxamide

7-(3-amino-1H-indazol-4-yl)-N-phenyl-2H-benzo[b][1,4]oxazine-4(3H)-carboxamide

Refernces

• 1、 Trabanco, Andrés A.,Tresadern, Gary,MacDonald, Gregor J.,Vega, Juan Antonio,De Lucas, Ana Isabel,Matesanz, Encarnación,García, Aránzazu,Linares, María Lourdes,Alonso De Diego, Sergio A.,Alonso, José Manuel,Oehlrich, Daniel,Ahnaou, Abdelah,Drinkenburg, Wilhelmus,MacKie, Claire,Andrés, José Ignacio,Lavreysen, Hilde,Cid, José María. "Imidazo[1,2-a]pyridines: Orally active positive allosteric modulators of the metabotropic glutamate 2 receptor". experimental part. p. 2688 - 2701. Retrieved 2012/06/01.