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

Name: methyl 3-amino-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate
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CAS No. 850689-26-8
Cat. No. CS-0006835
Purity≥98%
MDL No.MFCD18072669

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methyl 3-amino-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate|CS-0006835

Structure of 850689-26-8

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General Information

CAS No. 850689-26-8
Cat. No. CS-0006835
Purity ≥98%
MDL No. MFCD18072669
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₄H₂₀BNO₄
Molecular Weight 277.12
Synonym(s) METHYL3-AMINO-4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZOATE(WX192109)
SMILES O=C(OC)C1=CC=C(B2OC(C)(C)C(C)(C)O2)C(N)=C1

Description

Methyl 3-amino-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate is a boronate ester featuring a para-substituted aryl group with an electron-rich amino moiety. This bench-stable reagent integrates seamlessly into Suzuki-Miyaura cross-coupling reactions, enabling efficient C–C bond formation under mild conditions. The tetramethyl-1,3,2-dioxaborolan-2-yl group enhances stability and reactivity, while the methyl ester facilitates downstream functionalization.

Application

Methyl 3-amino-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate serves as a versatile Suzuki-Miyaura coupling building block, enabling efficient C–C bond formation under mild conditions. The boronate ester group exhibits high stability and functional group tolerance, while the amino and ester functionalities provide orthogonal reactivity for downstream modifications. Its bench-stable nature and ease of purification make it well-suited for iterative synthesis in medicinal chemistry and process development workflows.

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 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

Key Words

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

CAS No. 850689-26-8

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