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

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

CAS No. 948592-80-1
Cat. No. CS-0037883
Purity≥97%
MDL No.None

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4-Methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline|CS-0037883

Structure of 948592-80-1

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General Information

CAS No. 948592-80-1
Cat. No. CS-0037883
Purity ≥97%
MDL No. None
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₃H₂₀BNO₂
Molecular Weight 233.11
Synonym(s) 4-Methyl-2-(4,4,5,5-tetraMethyl-[1,3,2]dioxaborolan-2-yl)-phenylaMine
SMILES CC1=CC(=C(C=C1)N)B2OC(C)(C)C(C)(C)O2

Description

4-Methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline features a boronate ester group enabling reliable Suzuki-Miyaura coupling under standard conditions. The para-methyl substituent enhances electron density at the aryl ring, while the tetramethylcyclopentadienone moiety ensures excellent stability and moisture tolerance during handling. This compound integrates seamlessly into C–C bond formation workflows for complex heterocycles and functionalized biaryls.

Application

4-Methyl-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. Its stable boronate ester group enables efficient C–C bond formation under mild conditions, with excellent functional group tolerance and bench stability. The molecule functions effectively in the synthesis of substituted anilines, biaryl scaffolds, and complex heterocycles relevant to pharmaceutical and agrochemical development.

Synthesis

Route1
- In-stock
  
  583-68-6
- 25015-63-8
- ~87%
- In-stock
  
  948592-80-1
References
- Zhou, Fei; Driver, Tom G. Organic Letters, 2014 , vol. 16, # 11 p. 2916 - 2919
Route2
- In-stock
  
  29289-13-2
- 25015-63-8
- ~61%
- In-stock
  
  948592-80-1
References
- Soto, Sara; Vaz, Esther; Dell'Aversana, Carmela; Alvarez, Rosana; Altucci, Lucia; De Lera, Angel R. Organic and Biomolecular Chemistry, 2012 , vol. 10, # 10 p. 2101 - 2112
Route3
- In-stock
  
  583-68-6
- In-stock
  
  73183-34-3
- ~%
- In-stock
  
  948592-80-1
References
- Agarwal, Piyush K.; Saifuddin, Mohammad; Kundu, Bijoy Tetrahedron, 2010 , vol. 66, # 4 p. 862 - 870

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
Precautionary Statements : P264-P270-P330-P501

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Computational Chemistry Data

TPSA 44.48
LogP 1.87642
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Boronic Acid And Its Ester

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

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

CAS No. 948592-80-1

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