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

Name: 3-Chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline
Brand: ChemScene
Availability: InStock
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CAS No. 877160-63-9
Cat. No. CS-0101270
Purity≥97%
MDL No.MFCD09864184

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3-Chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline|CS-0101270

Structure of 877160-63-9

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General Information

CAS No. 877160-63-9
Cat. No. CS-0101270
Purity ≥97%
MDL No. MFCD09864184
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₂H₁₇BClNO₂
Molecular Weight 253.53
Synonym(s) 4-Amino-2-chlorophenylboronic acid, pinacol ester
SMILES NC1=CC=C(B2OC(C)(C)C(C)(C)O2)C(Cl)=C1

Description

3-Chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline features a boronate ester group enabling efficient Suzuki-Miyaura coupling under standard conditions. The electron-rich aryl moiety integrates seamlessly into complex molecular architectures, while the tetramethyl-substituted dioxaborolane enhances stability and reactivity. This bench-stable compound serves as a key building block for functionalized biaryls in medicinal chemistry and materials science.

Application

3-Chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline serves as a versatile boronate building block for Suzuki-Miyaura cross-coupling reactions. The pendant boronate ester group enables efficient coupling with aryl halides and pseudohalides under mild conditions, while the ortho-chloro substituent provides a site for further functionalization. Its stability, ease of handling, and compatibility with diverse reaction conditions make it ideal for constructing complex biaryl scaffolds in medicinal chemistry and materials science applications.

Synthesis

Route1
- In-stock
  
  73183-34-3
- ~%
- In-stock
  
  877160-63-9
References
- Journal of Organic Chemistry, , vol. 79, # 5 p. 1979 - 1988
Route2
- 121-87-9
- ~%
- In-stock
  
  877160-63-9
References
- Journal of Organic Chemistry, , vol. 79, # 5 p. 1979 - 1988

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

CAS No. 877160-63-9

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