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CS-W001157 4
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6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)quinazolin-2-amine

  • CAS No. 882670-92-0

  • Cat. No. CS-0174004
  • Purity≥97%
  • MDL No.None

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

6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)quinazolin-2-amine|CS-0174004

Structure of 882670-92-0

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General Information

  • CAS No. 882670-92-0
  • Cat. No. CS-0174004
  • Purity ≥97%
  • MDL No. None
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₄H₁₈BN₃O₂
  • Molecular Weight 271.12
  • Synonym(s) 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-quinazolinamine
  • SMILES N1=CC2=CC(=CC=C2N=C1N)B3OC(C)(C)C(O3)(C)C

Description

6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)quinazolin-2-amine features a boronate ester handle attached to a quinazoline scaffold, enabling direct incorporation into Suzuki-Miyaura cross-coupling reactions. The tetramethyl-substituted dioxaborolane moiety ensures high stability and reactivity under standard conditions, while the electron-deficient quinazoline core supports efficient coupling with aryl halides. This structure delivers rapid access to complex heterocyclic architectures in medicinal chemistry and materials science.

Application

6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)quinazolin-2-amine serves as a versatile boronate building block for palladium-catalyzed cross-coupling reactions. The tetramethylboronate group enables efficient Suzuki-Miyaura coupling under mild conditions, facilitating the construction of biaryl and heteroaryl scaffolds. Its stability under ambient conditions, ease of purification, and compatibility with diverse functional groups make it a practical reagent for medicinal chemistry and materials synthesis.

Synthesis

  • Route1

    References

    • Hu, Essa; Tasker, Andrew; White, Ryan D.; Kunz, Roxanne K.; Human, Jason; Chen, Ning; Buerli, Roland; Hungate, Randall; Novak, Perry; Itano, Andrea; Zhang, Xuxia; Yu, Violeta; Nguyen, Yen; Tudor, Yanyan; Plant, Matthew; Flynn, Shaun; Xu, Yang; Meagher, Kristin L.; Whittington, Douglas A.; Ng, Gordon Y. Journal of Medicinal Chemistry, 2008 , vol. 51, # 11 p. 3065 - 3068
  • Route2

    References

    • DiMauro, Erin F.; Newcomb, John; Nunes, Joseph J.; Bemis, Jean E.; Boucher, Christina; Buchanan, John L.; Buckner, William H.; Cee, Victor J.; Chai, Lilly; Deak, Holly L.; Epstein, Linda F.; Faust, Ted; Gallant, Paul; Geuns-Meyer, Stephanie D.; Gore, Anu; Gu, Yan; Henkle, Brad; Hodous, Brian L.; Hsieh, Faye; Huang, Xin; Kim, Joseph L.; Lee, Josie H.; Martin, Matthew W.; Masse, Craig E.; McGowan, David C.; Metz, Daniela; Mohn, Deanna; Morgenstern, Kurt A.; Oliveira-Dos-Santos, Antonio; Patel, Vinod F.; Powers, David; Rose, Paul E.; Schneider, Stephen; Tomlinson, Susan A.; Tudor, Yan-Yan; Turci, Susan M.; Welcher, Andrew A.; White, Ryan D.; Zhao, Huilin; Zhu, Li; Zhu, Xiaotian Journal of Medicinal Chemistry, 2006 , vol. 49, # 19 p. 5671 - 5686

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-P330-P362+P364-P405-P501

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Computational Chemistry Data

  • TPSA   70.26
  • LogP   1.5112
  • H_Acceptors   5
  • H_Donors   1
  • Rotatable_Bonds   1

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