2-Amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

Name: 2-Amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile
Brand: ChemScene
Availability: InStock
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CAS No. 934426-22-9
Cat. No. CS-0128682
Purity≥97%
MDL No.MFCD16996233

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2-Amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile|CS-0128682

Structure of 934426-22-9

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General Information

CAS No. 934426-22-9
Cat. No. CS-0128682
Purity ≥97%
MDL No. MFCD16996233
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₃H₁₇BN₂O₂
Molecular Weight 244.10
Synonym(s) (4-Amino-3-Cyanophenyl)Boronic Acid Pinacol Ester
SMILES N#CC1=CC(B2OC(C)(C)C(C)(C)O2)=CC=C1N

Description

This boronate-functionalized aryl amine integrates readily into Suzuki-Miyaura cross-coupling reactions under standard conditions. The tetramethyl-1,3,2-dioxaborolane moiety confers stability and moisture tolerance, while the para-cyano group enhances electronic modulation in downstream molecular architectures.

Application

2-Amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile serves as a versatile boron-containing building block for Suzuki-Miyaura cross-coupling reactions. The pendant boronate ester enables efficient C–C bond formation under mild conditions, while the amino and nitrile groups provide orthogonal functionality for further derivatization. Bench-stable and readily purified, it facilitates the construction of biaryl scaffolds relevant to medicinal chemistry and materials science.

Synthesis

Route1
- In-stock
  
  39263-32-6
- In-stock
  
  73183-34-3
- ~88%
- In-stock
  
  934426-22-9
References
- MYREXIS, INC.; HOLCOMB, Ryan; SUZUKI, Kazuyuki; HALTER, Robert J.; SEBAHAR, Paul R.; MCLEOD, Donald A.; SHENDEROVICH, Mark D.; YAGER, Kraig M.; BURSAVICH, Matthew Gregory; YUNGAI, Ashantai J.; RICHARDS, Burt; BARTEL, Paul L.; WETTSTEIN, Daniel A. Patent: WO2011/46970 A1, 2011 ; Location in patent: Page/Page column 91; 92 ; WO 2011/046970 A1
Route2
- In-stock
  
  132131-24-9
- In-stock
  
  73183-34-3
- ~68%
- In-stock
  
  934426-22-9
References
- ARROW THERAPEUTICS LIMITED Patent: WO2007/80401 A1, 2007 ; Location in patent: Page/Page column 26-27 ; WO 2007/080401 A1
Route3
- In-stock
  
  5922-60-1
- In-stock
  
  73183-34-3
- ~%
- In-stock
  
  934426-22-9
References
- SANOFI; ALCOUFFE, Chantal; BJEGARDE, Kirsten; MAUGER, Jacques Patent: WO2013/87744 A1, 2013 ; Location in patent: Page/Page column 27-28 ;

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-H312-H315-H319-H332-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 68.27
LogP 1.43968
H_Acceptors 4
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Boronic Acid And Its Ester

Building Blocks Functional Group Cyanide/Nitrile

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

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2-Amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

CAS No. 934426-22-9

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