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

Name: 4-Chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline
Brand: ChemScene
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CAS No. 1073371-77-3
Cat. No. CS-0044874
Purity≥97%
MDL No.MFCD06795672

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Excepted Quantity	$0.00
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4-Chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline|CS-0044874

Structure of 1073371-77-3

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General Information

CAS No. 1073371-77-3
Cat. No. CS-0044874
Purity ≥97%
MDL No. MFCD06795672
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₂H₁₇BClNO₂
Molecular Weight 253.53
Synonym(s) 4-chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenamine
SMILES NC1=CC=C(Cl)C=C1B2OC(C)(C)C(C)(C)O2

Description

This boronate-functionalized aniline integrates seamlessly into Suzuki-Miyaura cross-coupling reactions, offering enhanced stability and predictable reactivity. The para-chloro substituent enables selective derivatization, while the tetramethyl-dioxaborolane moiety ensures robustness under standard conditions. A bench-stable building block for complex molecular architectures in medicinal chemistry and materials science.

Application

4-Chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline serves as a versatile boron-based building block in Suzuki-Miyaura cross-coupling reactions. The arylboronate group enables efficient coupling with aryl and heteroaryl halides under mild conditions, while the aniline functionality provides a handle for further derivatization. Bench-stable and compatible with diverse functional groups, it facilitates rapid access to biaryl scaffolds common in medicinal chemistry and materials science.

Synthesis

Route1
- In-stock
  
  873-38-1
- 25015-63-8
- ~%
- In-stock
  
  1073371-77-3
References
- Angewandte Chemie - International Edition, , vol. 51, # 24 p. 5920 - 5923
Route2
- 106-47-8
- ~%
- In-stock
  
  1073371-77-3
References
- Angewandte Chemie - International Edition, , vol. 52, # 49 p. 12915 - 12919 Angew. Chem., , 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

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

CAS No. 1073371-77-3

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