Methyl 4-amino-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

Name: Methyl 4-amino-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate
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CAS No. 524916-42-5
Cat. No. CS-0174001
Purity≥98%
MDL No.None

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Methyl 4-amino-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate|CS-0174001

Structure of 524916-42-5

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General Information

CAS No. 524916-42-5
Cat. No. CS-0174001
Purity ≥98%
MDL No. None
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₄H₂₀BNO₄
Molecular Weight 277.12
Synonym(s) Benzoic acid, 4-amino-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-,methyl ester
SMILES CC1(C(C)(OB(O1)C2=C(N)C=CC(C(OC)=O)=C2)C)C

Description

Methyl 4-amino-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate features a boronate ester group enabling efficient Suzuki-Miyaura cross-coupling under mild conditions. The para-amino substituent imparts enhanced reactivity and solubility in polar solvents, while the tetramethyl-substituted dioxaborolane ring ensures high stability and moisture tolerance. This compound integrates readily into complex molecular architectures with minimal side reactions.

Application

Methyl 4-amino-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate serves as a versatile boron-containing building block for Suzuki-Miyaura cross-coupling reactions. The boronate ester group enables reliable C–C bond formation under mild conditions, while the methyl ester and primary amine functionalities provide orthogonal handles for further derivatization. Bench-stable and compatible with diverse reaction conditions, it facilitates efficient synthesis of biaryl and heteroaryl scaffolds relevant to medicinal chemistry and materials science.

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+P364

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Computational Chemistry Data

TPSA 70.78
LogP 1.3546
H_Acceptors 5
H_Donors 1
Rotatable_Bonds 2

Other Classifications

Building Blocks Functional Group Boronic Acid And Its Ester

Building Blocks Functional Group Ester

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

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Methyl 4-amino-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

CAS No. 524916-42-5

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