2-Fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

CAS No. 1003575-43-6
Cat. No. CS-W006140
Purity≥97%
MDL No.MFCD11044430

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2-Fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline|CS-W006140

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Description

2-Fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline features a boronate ester group enabling reliable Suzuki-Miyaura coupling under mild conditions. The fluorine substituent enhances electronic modulation and metabolic stability in bioactive molecule synthesis. This bench-stable reagent combines high functional group tolerance with excellent handling properties, streamlining access to complex arylated scaffolds in medicinal chemistry and materials science applications.

Application

2-Fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline serves as a versatile boron-containing building block for Suzuki-Miyaura cross-coupling reactions. The ortho-fluoro substituent enables directed ortho-metalation and facilitates downstream functionalization, while the stable pinacol boronate group ensures excellent bench stability and compatibility with a wide range of coupling partners. This reagent functions effectively in both small-molecule synthesis and heterocyclic scaffold construction, offering predictable regioselectivity and high yields under standard reaction conditions.

General Information

CAS No. 1003575-43-6
Cat. No. CS-W006140
Purity ≥97%
MDL No. MFCD11044430
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₂H₁₇BFNO₂
Molecular Weight 237.08
Synonym(s) 3-Amino-4-fluorophenylboronic Acid Pinacol Ester
SMILES NC1=CC(B2OC(C)(C)C(C)(C)O2)=CC=C1F

Computational Chemistry Data

TPSA 44.48
LogP 1.7071
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 1

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 : H302
Precautionary Statements : P264-P270-P330-P501

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Other Classifications

Building Blocks Functional Group Fluoride

Building Blocks Functional Group Boronic Acid And Its Ester

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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2-Fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

CAS No. 1003575-43-6

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