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CS-W001157 4
Total: USD 88.00

Diethyl 4-bromobenzylphosphonate

  • CAS No. 38186-51-5

  • Cat. No. CS-0005897
  • Purity≥97%
  • MDL No.MFCD05663693

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

Diethyl 4-bromobenzylphosphonate|CS-0005897

Structure of 38186-51-5

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General Information

  • CAS No. 38186-51-5
  • Cat. No. CS-0005897
  • Purity ≥97%
  • MDL No. MFCD05663693
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₁₆BrO₃P
  • Molecular Weight 307.12
  • Synonym(s) Diethyl(4-Bromobenzyl)Phosphonate
  • SMILES O=P(OCC)(OCC)CC1=CC=C(Br)C=C1

Description

Diethyl 4-bromobenzylphosphonate features a brominated benzyl group linked to a phosphonate ester, enabling direct functionalization in cross-coupling reactions. This bench-stable reagent integrates readily into synthetic sequences requiring aryl halide equivalents, offering high compatibility with palladium-catalyzed transformations and efficient access to phosphonate-containing architectures.

Application

Diethyl 4-bromobenzylphosphonate serves as a versatile building block for C–C bond formation via Negishi and Suzuki-Miyaura coupling reactions. The bromide moiety enables palladium-catalyzed cross-coupling with arylboranes and organozinc reagents, while the phosphonate group supports Stetter and Michael addition reactions. Its bench-stable nature and compatibility with diverse functional groups facilitate efficient synthesis of biaryl and heterocyclic scaffolds in medicinal chemistry workflows.

Synthesis

  • Route1
    • N'-(4-bromobenzylidene)-4-methylbenzenesulfonohydrazide|CS-0191666
      19350-68-6
    • null|null
      762-04-9
    • ~88%
    • In-stock
      Diethyl 4-bromobenzylphosphonate|CS-0005897
      38186-51-5

    References

    • Miao, Wenjun; Gao, Yuzhen; Li, Xueqin; Gao, Yuxing; Tang, Guo; Zhao, Yufen Advanced Synthesis and Catalysis, 2012 , vol. 354, # 14-15 p. 2659 - 2664
  • Route2
    • In-stock
      α,4-Dibromotoluene|CS-W009136
      589-15-1
    • null|null
      122-52-1
    • ~99%
    • In-stock
      Diethyl 4-bromobenzylphosphonate|CS-0005897
      38186-51-5

    References

    • Urbani, Maxence; Ohkubo, Kei; Islam, D. M. Shafiqul; Fukuzumi, Shunichi; Langa, Fernando Chemistry - A European Journal, 2012 , vol. 18, # 24 p. 7473 - 7485
  • Route3

    References

    • Rout, Laxmidhar; Regati, Sridhar; Zhao, Cong-Gui Advanced Synthesis and Catalysis, 2011 , vol. 353, # 18 p. 3340 - 3346

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

Quality Control

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Computational Chemistry Data

  • TPSA   35.53
  • LogP   4.2152
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   6

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