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

Name: 2-Chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline
Brand: ChemScene
Availability: InStock
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CAS No. 721960-43-6
Cat. No. CS-0101292
Purity≥97%
MDL No.MFCD09998359

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
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2-Chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline|CS-0101292

Structure of 721960-43-6

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General Information

CAS No. 721960-43-6
Cat. No. CS-0101292
Purity ≥97%
MDL No. MFCD09998359
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₂H₁₇BClNO₂
Molecular Weight 253.53
Synonym(s) 4-Amino-3-Chlorophenylboronic Acid,Pinacol Ester
SMILES NC1=CC=C(B2OC(C)(C)C(C)(C)O2)C=C1Cl

Description

2-Chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline features a boronate ester group enabling efficient Suzuki-Miyaura coupling, while the ortho-chloro substituent provides a handle for further functionalization. This bench-stable reagent integrates seamlessly into cross-coupling workflows, offering predictable reactivity and compatibility with diverse reaction conditions.

Application

2-Chloro-4-(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 boronate ester group enables efficient coupling with aryl and heteroaryl halides under mild conditions, while the ortho-chloro substituent provides a site for further functionalization. Its bench-stable, crystalline nature facilitates handling and purification, making it well-suited for iterative synthesis of biaryl scaffolds in medicinal chemistry and materials science applications.

Synthesis

Route1
- In-stock
  
  38762-41-3
- In-stock
  
  73183-34-3
- ~43%
- In-stock
  
  721960-43-6
References
- BOEHRINGER INGELHEIM INTERNATIONAL GmbH; BOEHRINGER INGELHEIM PHARMA GmbH and CO KG Patent: WO2005/118575 A1, 2005 ; Location in patent: Page/Page column 80-81 ; WO 2005/118575 A1
Route2
- In-stock
  
  38762-41-3
- 25015-63-8
- ~49%
- In-stock
  
  721960-43-6
References
- X-CEPTOR THERAPEUTICS, INC.; SANKYO COMPANY, LIMITED Patent: WO2004/58717 A1, 2004 ; Location in patent: Page 80 ; WO 2004/058717 A1

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

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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

Key Words

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

CAS No. 721960-43-6

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