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2-Amino-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-nicotinonitrile

  • CAS No. 1246372-66-6

  • Cat. No. CS-0183545
  • Purity≥97%
  • MDL No.None

*For research and further manufacturing use only, not for direct human use.

2-Amino-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-nicotinonitrile|CS-0183545

Structure of 1246372-66-6

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General Information

  • CAS No. 1246372-66-6
  • Cat. No. CS-0183545
  • Purity ≥97%
  • MDL No. None
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₁₆BN₃O₂
  • Molecular Weight 245.09
  • Synonym(s) 2-Amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinonitrile
  • SMILES CC1(C)C(C)(C)OB(C2=CNC(=N)C(=C2)C#N)O1

Description

This boronate-functionalized nicotinonitrile integrates readily into Suzuki-Miyaura coupling reactions under standard conditions. The tetramethyl-dioxaborolane moiety provides exceptional stability and moisture tolerance, enabling efficient cross-coupling with aryl halides. The para-nitrogen functionality enhances electronic modulation in complex heterocyclic systems, offering a reliable handle for constructing bioactive scaffolds.

Application

2-Amino-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-nicotinonitrile serves as a versatile boronate building block for Suzuki-Miyaura cross-coupling reactions. The tetramethylboronate moiety enables stable, room-temperature handling and broad functional group tolerance. It facilitates efficient C–C bond formation with aryl and heteroaryl halides, making it ideal for constructing substituted nicotinonitrile scaffolds commonly found in medicinal chemistry and agrochemical research.

Synthesis

  • Route1

    References

    • OTSUKA PHARMACEUTICAL CO., LTD.; ABUDUSAIMI, Mamuti; YE, Fangguo; SUN, Jiangqin; MIYAMOTO, Hisashi; CHENG, Jay-Fei; OKA, Daisuke Patent: WO2013/29548 A1, 2013 ; Location in patent: Page/Page column 87 ;
  • Route2

    References

    • OTSUKA PHARMACEUTICAL CO., LTD.; ABUDUSAIMI, Mamuti; YE, Fangguo; SUN, Jiangqin; MIYAMOTO, Hisashi; CHENG, Jay-Fei; OKA, Daisuke Patent: WO2013/29548 A1, 2013 ;

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   81.89
  • LogP   0.66505
  • H_Acceptors   4
  • H_Donors   2
  • Rotatable_Bonds   1

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