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5-Bromo-2-methoxybenzonitrile

  • CAS No. 144649-99-0

  • Cat. No. CS-0042159
  • Purity≥97%
  • MDL No.MFCD00143429

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

5-Bromo-2-methoxybenzonitrile|CS-0042159

Structure of 144649-99-0

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General Information

  • CAS No. 144649-99-0
  • Cat. No. CS-0042159
  • Purity ≥97%
  • MDL No. MFCD00143429
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₆BrNO
  • Molecular Weight 212.04
  • Synonym(s) 5-Bromo-o-anisyl cyanide
  • SMILES N#CC1=CC(Br)=CC=C1OC

Description

5-Bromo-2-methoxybenzonitrile features a bromine substituent at the 5-position and a methoxy group at the 2-position, flanking a nitrile moiety on a benzene ring. This electron-deficient aryl halide enables efficient cross-coupling reactions under palladium catalysis. The methoxy group enhances solubility while maintaining stability under standard conditions.

Application

5-Bromo-2-methoxybenzonitrile serves as a versatile building block in medicinal chemistry and materials science, enabling palladium-catalyzed cross-coupling reactions due to its well-defined bromine and nitrile functionalities. The methoxy group enhances solubility and modulates electronic properties, while the molecule exhibits excellent bench stability and facilitates straightforward purification. Its orthogonal reactivity profile supports sequential functionalization in complex molecule synthesis.

Synthesis

  • Route1

    References

    • Glaxo Group Limited Patent: US2009/197871 A1, 2009 ; Location in patent: Page/Page column 53-54 ; US 20090197871 A1
  • Route2

    References

    • Raynham, Tony Michael; Hammonds, Timothy Robin; Gilliatt, Julia Helen; Charles, Mark David; Pave, Gregoire Alexandre; Foxton, Caroline Heather; Carr, James Lindsay; Mistry, Neela Sumit Patent: US2009/247519 A1, 2009 ; Location in patent: Page/Page column 143 ;
  • Route3

    References

    • Anbarasan, Pazhamalai; Neumann, Helfried; Beller, Matthias Chemistry - A European Journal, 2011 , vol. 17, # 15 p. 4217 - 4222

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+H332
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P501

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Computational Chemistry Data

  • TPSA   33.02
  • LogP   2.32938
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   1

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