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

Name: 5-Chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 863578-21-6
Cat. No. CS-0021734
Purity≥96%
MDL No.MFCD11617915

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5-Chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline|CS-0021734

Structure of 863578-21-6

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General Information

CAS No. 863578-21-6
Cat. No. CS-0021734
Purity ≥96%
MDL No. MFCD11617915
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₂H₁₇BClNO₂
Molecular Weight 253.53
Synonym(s) 5-Chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)
SMILES NC1=CC(Cl)=CC=C1B2OC(C)(C)C(C)(C)O2

Description

This boronate ester integrates a chloro-substituted aniline scaffold, enabling direct coupling in Suzuki-Miyaura reactions. The tetramethyl-1,3,2-dioxaborolane moiety confers stability and enhanced reactivity under standard conditions. Designed for efficient C–N bond formation, this reagent facilitates rapid access to functionalized arylamines in synthetic workflows.

Application

5-Chloro-2-(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 pendant boronate ester enables efficient C–C bond formation under mild conditions, while the chloro and amine groups provide orthogonal reactivity for sequential functionalization. Bench-stable and readily purified by standard chromatography, it functions as a key intermediate in the synthesis of biaryl scaffolds and functionalized heterocycles relevant to medicinal chemistry and materials science.

Synthesis

Route1
- In-stock
  
  823-57-4
- 25015-63-8
- ~63%
- In-stock
  
  863578-21-6
References
- Japan Tobacco, Inc. Patent: EP1719773 A1, 2006 ; Location in patent: Example 1-10 ;
Route2
- In-stock
  
  823-57-4
- ~96%
- In-stock
  
  863578-21-6
References
- CONSTELLATION PHARMACEUTICALS, INC.; ALBRECHT, Brian, K.; GEHLING, Victor, S.; TAYLOR, Alexander, M.; VASWANI, Rishi, G. Patent: WO2013/184878 A1, 2013 ; Location in patent: Paragraph 00183; 00184 ;
Route3
- 108-42-9
- In-stock
  
  73183-34-3
- 25015-63-8
- ~36%
- In-stock
  
  863578-21-6
- In-stock
  
  1269233-11-5
References
- Preshlock, Sean M.; Plattner, Donald L.; Maligres, Peter E.; Krska, Shane W.; Maleczka Jr., Robert E.; Smith III, Milton R. Angewandte Chemie - International Edition, 2013 , vol. 52, # 49 p. 12915 - 12919 Angew. Chem., 2013 , vol. 125, # 49 p. 13153 - 13157,5

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 44.48
LogP 2.2214
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Chloride

Building Blocks Functional Group Boronic Acid And Its Ester

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

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

CAS No. 863578-21-6

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