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1224844-66-9

1224844-66-9 Structure

1224844-66-9 Structure
IdentificationBack Directory
[Name]

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

1224844-66-9
[Synonyms]

2-aminobenzo[d]oxazol-5-ylboronic acid pinacol ester
5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-benzoxazol-2-amine
2-Amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoxazole
2-Benzoxazolamine, 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-
5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2yl)benzo[d]oxazol-2-amine
5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-benzoxazol-2-amine
[Molecular Formula]

C13H17BN2O3
[MDL Number]

MFCD13182075
[MOL File]

1224844-66-9.mol
[Molecular Weight]

260.1
Chemical PropertiesBack Directory
[Boiling point ]

411.7±37.0 °C(Predicted)
[density ]

1.19±0.1 g/cm3(Predicted)
[storage temp. ]

under inert gas (nitrogen or Argon) at 2–8 °C
[pka]

1.75±0.10(Predicted)
[Appearance]

Light yellow to brown Solid
Safety DataBack Directory
[Symbol(GHS) ]

GHS hazard pictograms
GHS07
[Signal word ]

Warning
[Hazard statements ]

H302+H312+H332-H315-H319-H335
[Precautionary statements ]

P261-P280-P305+P351+P338
Hazard InformationBack Directory
[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.
[Synthesis]

Bis(pinacolato)diboron

73183-34-3

5-BROMOBENZO[D]OXAZOL-2-AMINE

64037-07-6

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

1224844-66-9

Specific operation: 127 g of 2-amino-5-bromobenzoxazole, 182 g of pinacol ester of bisboronic acid, 45 g of 1,1'-bis(diphenylphosphino)ferrocene palladium dichloride (dppf palladium chloride) and 180 g of potassium acetate were added to 2 L of 1,4-dioxane. The mixture was refluxed under nitrogen protection for 3 h. After cooling to room temperature, the mixture was filtered and the filtrate was concentrated to give the crude product 2-aminobenzoxazole-5-boronate. The crude product was dissolved in 500 mL of petroleum ether, stirred for 1 hr and filtered, and the filter cake was dried under vacuum at 50 °C to give 110 g of purified 2-amino benzoxazole-5-boronic acid ester in 89.5% yield.

[References]

[1] Patent: CN105130973, 2018, B. Location in patent: Paragraph 0053; 0069-0071
[2] Patent: WO2013/23184, 2013, A1. Location in patent: Paragraph 00233; 00234
[3] Patent: US2018/65983, 2018, A1
[4] Patent: WO2010/51042, 2010, A1. Location in patent: Page/Page column 27; 133; 219
[5] Patent: WO2013/71272, 2013, A1. Location in patent: Paragraph 00256-00275
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