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CS-W001157 4
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1-Bromo-3-ethylbenzene

  • CAS No. 2725-82-8

  • Cat. No. CS-0020133
  • Purity≥98%
  • MDL No.MFCD00156128

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

1-Bromo-3-ethylbenzene|CS-0020133

Structure of 2725-82-8

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General Information

  • CAS No. 2725-82-8
  • Cat. No. CS-0020133
  • Purity ≥98%
  • MDL No. MFCD00156128
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₉Br
  • Molecular Weight 185.06
  • Synonym(s) (3-Ethylphenyl)bromide; 3-Bromo-1-ethylbenzene; 3-Ethylbromobenzene; 3-Bromoethylbenzene
  • SMILES CCC1=CC(Br)=CC=C1

Description

1-Bromo-3-ethylbenzene features a bromine substituent ortho to an ethyl group on the benzene ring, enabling selective cross-coupling reactions. This configuration delivers enhanced regiocontrol in palladium-catalyzed transformations, particularly Suzuki-Miyaura and Stille couplings. The molecule exhibits favorable stability under standard reaction conditions and integrates readily into complex molecular architectures.

Application

1-Bromo-3-ethylbenzene serves as a versatile aryl halide building block in cross-coupling reactions, enabling efficient C–C bond formation under palladium-catalyzed conditions. The ortho-ethyl substituent provides steric and electronic modulation, enhancing regioselectivity in Suzuki-Miyaura and Negishi couplings. Bench-stable and readily purified by distillation, it functions reliably in the synthesis of functionalized biaryls and complex pharmaceutical intermediates.

Synthesis

  • Route1

    References

    • Takeda Chemical Industries, Ltd. Patent: EP1402900 A1, 2004 ;
  • Route2

    References

    • Dong, Hailin; Berke, Heinz Journal of Organometallic Chemistry, 2011 , vol. 696, # 9 p. 1803 - 1808
  • Route3

    References

    • Takeda Chemical Industries, Ltd. Patent: EP1402900 A1, 2004 ;

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   0
  • LogP   3.0115
  • H_Acceptors   0
  • H_Donors   0
  • Rotatable_Bonds   1

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