8-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-benzo[b][1,4]oxazin-3(4H)-one

Name: 8-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-benzo[b][1,4]oxazin-3(4H)-one
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CAS No. 1551418-99-5
Cat. No. CS-0369237
Purity≥95%
MDL No.MFCD30290233

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8-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-benzo[b][1,4]oxazin-3(4H)-one|CS-0369237

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General Information

CAS No. 1551418-99-5
Cat. No. CS-0369237
Purity ≥95%
MDL No. MFCD30290233
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₄H₁₈BNO₄
Molecular Weight None
Synonym(s) 3-Oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-8-boronic Acid Pinacol Ester
SMILES O=C1COC2=C(B3OC(C)(C)C(C)(C)O3)C=CC=C2N1

Description

8-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-benzo[b][1,4]oxazin-3(4H)-one features a boronate ester handle appended to a fused oxazine scaffold, enabling direct coupling in Suzuki-Miyaura transformations. This bench-stable reagent integrates readily into complex molecule assembly, delivering efficient access to functionalized heterocyclic architectures under mild conditions.

Application

8-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-benzo[b][1,4]oxazin-3(4H)-one serves as a versatile boronate building block for palladium-catalyzed cross-coupling reactions. Its oxazinone core provides structural rigidity and metabolic stability, while the pinacol boronate group enables efficient C–C bond formation under mild conditions. The compound exhibits excellent bench stability, facile purification, and broad functional group tolerance, making it well-suited for iterative synthesis of complex heterocyclic scaffolds in medicinal chemistry and materials science applications.

Safety Information

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GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H315-H319
Precautionary Statements : P264-P280-P302+P352-P362

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Computational Chemistry Data

TPSA 56.79
LogP 1.3167
H_Acceptors 4
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds Other aromatic heterocycles compounds

Key Words

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8-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-benzo[b][1,4]oxazin-3(4H)-one

CAS No. 1551418-99-5

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