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CS-W001157 4
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1-(2-Bromoethyl)-3-methoxybenzene

  • CAS No. 2146-61-4

  • Cat. No. CS-0046308
  • Purity≥98%
  • MDL No.MFCD07369789

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

1-(2-Bromoethyl)-3-methoxybenzene|CS-0046308

Structure of 2146-61-4

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General Information

  • CAS No. 2146-61-4
  • Cat. No. CS-0046308
  • Purity ≥98%
  • MDL No. MFCD07369789
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₁₁BrO
  • Molecular Weight 215.09
  • Synonym(s) 3-Methoxyphenethyl bromide
  • SMILES COC1=CC(CCBr)=CC=C1

Description

1-(2-Bromoethyl)-3-methoxybenzene features a bromoethyl chain appended to a methoxy-substituted benzene ring, enabling direct functionalization in cross-coupling and nucleophilic substitution reactions. The electron-donating methoxy group enhances reactivity at the ortho position, while the terminal bromide offers high chemoselectivity for transition metal-catalyzed transformations. This compound serves as a key intermediate in synthesizing bioactive molecules and functional polymers.

Application

1-(2-Bromoethyl)-3-methoxybenzene serves as a versatile synthetic building block for the construction of functionalized aromatic ethers and heterocyclic systems. The bromoethyl side chain enables efficient Suzuki, Negishi, and Sonogashira coupling reactions, while the methoxy group provides moderate electron-donating character and ortho-directing influence. Its bench-stable crystalline form facilitates handling and purification, making it well-suited for iterative synthesis in medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • Collins, David J.; Fallon, Gary D.; Skene, Colin E. Australian Journal of Chemistry, 1992 , vol. 45, # 1 p. 71 - 97
  • Route2

    References

    • Bioorganic and Medicinal Chemistry, , vol. 8, # 7 p. 1757 - 1766
  • Route3

    References

    • Bioorganic and Medicinal Chemistry, , vol. 8, # 7 p. 1757 - 1766

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS05,GHS07
Signal Word : Danger
UN#: 3265
Class : 8
Packing Group : Ⅱ
Hazard Statements : H302-H314
Precautionary Statements : P260-P264-P270-P280-P301+P330+P331-P304+P340-P330-P363-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   9.23
  • LogP   2.6326
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   3

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