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1-(Bromomethyl)-4-chloro-2-fluorobenzene

  • CAS No. 71916-82-0

  • Cat. No. CS-0128822
  • Purity≥98%
  • MDL No.MFCD00831105

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

1-(Bromomethyl)-4-chloro-2-fluorobenzene|CS-0128822

Structure of 71916-82-0

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General Information

  • CAS No. 71916-82-0
  • Cat. No. CS-0128822
  • Purity ≥98%
  • MDL No. MFCD00831105
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₅BrClF
  • Molecular Weight 223.47
  • Synonym(s) 4-Chloro-2-fluorobenzyl bromide
  • SMILES FC1=CC(Cl)=CC=C1CBr

Description

1-(Bromomethyl)-4-chloro-2-fluorobenzene features a bromomethyl group flanked by electron-withdrawing chlorine and fluorine substituents, enhancing electrophilic reactivity. This ortho-fluoro, para-chloro aryl halide integrates readily into cross-coupling reactions and serves as a selective building block for functionalized aromatic systems under standard conditions.

Application

1-(Bromomethyl)-4-chloro-2-fluorobenzene serves as a versatile aryl building block for transition-metal-catalyzed couplings, enabling efficient construction of biaryl and heterocyclic scaffolds. The bromomethyl group facilitates nucleophilic substitution and cross-coupling reactions, while the ortho-fluoro and para-chloro substituents provide orthogonal reactivity and enhanced stability under standard synthetic conditions. Its bench-stable nature and compatibility with palladium-catalyzed transformations make it well-suited for iterative synthesis in medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • Kelly, Stephen M.; Schad, Hanspeter Helvetica Chimica Acta, 1985 , vol. 68, p. 1444 - 1452
  • Route2

    References

    • Al-Darwich; Plenevaux; Lemaire; Fiore; Christiaens; Comar; Luxen Journal of Fluorine Chemistry, 1996 , vol. 80, # 2 p. 117 - 124
  • Route3

    References

    • Helvetica Chimica Acta, , vol. 68, p. 1444 - 1452

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS05
Signal Word : Danger
UN#: 1760
Class : 8
Packing Group : Ⅲ
Hazard Statements : H227-H290-H314
Precautionary Statements : P210-P234-P260-P264-P280-P301+P330+P331-P304+P340-P363-P390-P405-P406-P501

Quality Control

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Computational Chemistry Data

  • TPSA   0
  • LogP   3.374
  • H_Acceptors   0
  • H_Donors   0
  • Rotatable_Bonds   1

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