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

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

CAS No. 882678-96-8
Cat. No. CS-0008630
Purity≥97%
MDL No.MFCD11054038

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
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2-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline|CS-0008630

Structure of 882678-96-8

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General Information

CAS No. 882678-96-8
Cat. No. CS-0008630
Purity ≥97%
MDL No. MFCD11054038
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₃H₂₀BNO₂
Molecular Weight 233.11
Synonym(s) 3-AMino-2-Metyl phenyl boronicacid pinacol ester
SMILES NC1=CC=CC(B2OC(C)(C)C(C)(C)O2)=C1C

Description

2-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline features a boronate ester group enabling efficient Suzuki-Miyaura coupling under mild conditions. The electron-rich aniline moiety enhances reactivity, while the tetramethyl-substituted dioxaborolane imparts excellent stability and moisture tolerance. This bench-stable building block streamlines access to functionalized biaryls in medicinal chemistry and materials synthesis.

Application

2-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline serves as a versatile boron-containing building block in palladium-catalyzed cross-coupling reactions. Its stable boronate ester group enables efficient Suzuki-Miyaura coupling with aryl and heteroaryl halides, facilitating the construction of biaryl and extended conjugated systems. The molecule exhibits excellent bench stability, minimal protodeboronation, and compatibility with diverse functional groups, making it ideal for iterative synthesis workflows in medicinal chemistry and materials science.

Synthesis

Route1
- 910235-64-2
- ~99%
- In-stock
  
  882678-96-8
References
- CGI PHARMACEUTICALS, INC.; GENENTECH, INC. Patent: WO2009/137596 A1, 2009 ; Location in patent: Page/Page column 69-70 ; WO 2009/137596 A1
Route2
- In-stock
  
  87-60-5
- In-stock
  
  73183-34-3
- ~38%
- In-stock
  
  882678-96-8
References
- GENENTECH, INC.; SUMITOMO CHEMICAL COMPANY, LIMITED Patent: US2012/123122 A1, 2012 ; Location in patent: Page/Page column 14 ;
Route3
- In-stock
  
  172681-47-9
- In-stock
  
  73183-34-3
- ~%
- In-stock
  
  882678-96-8
References
- US2007/54916 A1, ; Page/Page column 108 ;

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

Quality Control

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

CAS No. 882678-96-8

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