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

Name: 2-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline
Brand: ChemScene
Availability: InStock
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CAS No. 590418-05-6
Cat. No. CS-0037062
Purity≥97%
MDL No.MFCD09033882

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Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
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2-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline|CS-0037062

Structure of 590418-05-6

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General Information

CAS No. 590418-05-6
Cat. No. CS-0037062
Purity ≥97%
MDL No. MFCD09033882
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₃H₂₀BNO₂
Molecular Weight 233.11
Synonym(s) 2-METHYL-4-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-PHENYLAMINE
SMILES CC1=CC(=CC=C1N)B2OC(C)(C)C(C)(C)O2

Description

2-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline delivers a boronate ester group flanked by a methyl-substituted aniline scaffold, enabling efficient Suzuki-Miyaura cross-coupling under standard conditions. This bench-stable reagent integrates readily into molecular architectures requiring directed functionalization at the para-position of an aromatic amine.

Application

2-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline serves as a robust boronate building block for Suzuki-Miyaura cross-coupling reactions. Its stable pinacol boronate group enables efficient coupling with aryl and heteroaryl halides under mild conditions. The molecule exhibits excellent bench stability, tolerates a range of functional groups, and facilitates rapid access to substituted aniline scaffolds commonly found in pharmaceutical intermediates and agrochemicals.

Synthesis

Route1
- In-stock
  
  583-75-5
- In-stock
  
  73183-34-3
- ~20%
- In-stock
  
  590418-05-6
References
- EVOLVA SA; HEIM, Jutta; SCHNEIDER, Peter; ROUSSEL, Patrick; MILLIGAN, Daniel Patent: WO2012/104305 A1, 2012 ; Location in patent: Page/Page column 150 ;
Route2
- In-stock
  
  590418-04-5
- ~%
- In-stock
  
  590418-05-6
References
- Shoda, Motoshi; Kuriyama, Hiroshi Patent: US2004/44258 A1, 2004 ; Location in patent: Page 157 ;

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 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

Key Words

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

CAS No. 590418-05-6

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