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

Name: N-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline
Brand: ChemScene
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CAS No. 845870-55-5
Cat. No. CS-0101256
Purity≥97%
MDL No.MFCD06795668

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N-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline|CS-0101256

Structure of 845870-55-5

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General Information

CAS No. 845870-55-5
Cat. No. CS-0101256
Purity ≥97%
MDL No. MFCD06795668
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₃H₂₀BNO₂
Molecular Weight 233.12
Synonym(s) 4-(N-Methylamino)Phenylboronic Acid, Pinacol Ester
SMILES CC1(C)C(C)(C)OB(C2=CC=C(NC)C=C2)O1

Description

N-Methyl-4-(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. This bench-stable reagent integrates seamlessly into C–C bond formation workflows, delivering high functional group tolerance and predictable regioselectivity in complex molecular architectures.

Application

N-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline serves as a robust boron-containing building block for Suzuki-Miyaura cross-coupling reactions. Its stable boronate ester group enables efficient C–C bond formation under mild conditions, while the N-methyl aniline moiety provides excellent functional group tolerance and enhanced solubility. This reagent facilitates the construction of biaryl scaffolds with high reproducibility and is well-suited for both small-molecule library synthesis and process-scale applications.

Synthesis

Route1
- In-stock
  
  932-96-7
- 25015-63-8
- ~80%
- In-stock
  
  845870-55-5
- 100-61-8
References
- Synlett, , # 12 p. 1867 - 1870

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 30.49
LogP 2.0275
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 2

Other Classifications

Building Blocks Functional Group Boronic Acid And Its Ester

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

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

CAS No. 845870-55-5

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