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CS-W001157 4
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4-Bromo-2-methylbenzonitrile

  • CAS No. 67832-11-5

  • Cat. No. CS-W002196
  • Purity≥97%
  • MDL No.MFCD00041461

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

4-Bromo-2-methylbenzonitrile|CS-W002196

Structure of 67832-11-5

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General Information

  • CAS No. 67832-11-5
  • Cat. No. CS-W002196
  • Purity ≥97%
  • MDL No. MFCD00041461
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₆BrN
  • Molecular Weight 196.04
  • Synonym(s) 5-Bromo-2-cyanotoluene
  • SMILES N#Cc1ccc(cc1C)Br

Description

4-Bromo-2-methylbenzonitrile is a halogenated aromatic nitrile featuring a bromine atom at the para position relative to the cyano group and a methyl substituent ortho to the nitrile. This electronic and steric profile enables efficient coupling in cross-coupling reactions, particularly Suzuki-Miyaura and Negishi transformations, under standard conditions. The molecule exhibits bench-stable handling characteristics and good solubility in common organic solvents, facilitating integration into multi-step synthesis workflows.

Application

4-Bromo-2-methylbenzonitrile serves as a versatile building block in medicinal chemistry and agrochemical synthesis, enabling palladium-catalyzed cross-coupling reactions due to its stable aryl bromide and nitrile functionalities. The ortho-methyl group enhances electronic modulation and provides steric control in subsequent transformations. Its bench-stable nature and compatibility with diverse reaction conditions facilitate efficient access to substituted biaryls, heterocycles, and complex scaffolds in multi-step syntheses.

Synthesis

  • Route1

    References

    • Journal of Organic Chemistry, , vol. 27, p. 1426 - 1430
  • Route2
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    • In-stock
      4-Bromo-2-methylbenzonitrile|CS-W002196
      67832-11-5

    References

    • Journal of Organic Chemistry, , vol. 27, p. 1426 - 1430
  • Route3

    References

    • Journal of Organic Chemistry, , vol. 27, p. 1426 - 1430

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
Precautionary Statements : P264-P270-P330-P501

Quality Control

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Computational Chemistry Data

  • TPSA   23.79
  • LogP   2.6292
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   0

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