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CS-W001157 4
Total: USD 88.00

2-Bromo-N-phenylacetamide

  • CAS No. 5326-87-4

  • Cat. No. CS-D0368
  • Purity≥98%
  • MDL No.MFCD00462518

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

2-Bromo-N-phenylacetamide|CS-D0368

Structure of 5326-87-4

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General Information

  • CAS No. 5326-87-4
  • Cat. No. CS-D0368
  • Purity ≥98%
  • MDL No. MFCD00462518
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₈BrNO
  • Molecular Weight 214.06
  • Synonym(s) N-Phenyl-2-bromoacetamide
  • SMILES O=C(NC1=CC=CC=C1)CBr

Description

2-Bromo-N-phenylacetamide features a bromine atom at the alpha position relative to the amide carbonyl, enhancing its reactivity in nucleophilic substitution and coupling processes. This bench-stable compound integrates readily into synthetic sequences requiring electrophilic functionality, particularly in the construction of aryl-substituted heterocycles and bioactive intermediates.

Application

2-Bromo-N-phenylacetamide serves as a versatile building block in synthetic organic chemistry, enabling efficient access to substituted anilines and heterocyclic scaffolds via palladium-catalyzed cross-coupling reactions. Its bromo group facilitates reliable C–C and C–N bond formation under standard coupling conditions, while the amide functionality provides stability and compatibility with diverse reaction environments. The compound exhibits excellent bench stability and is readily purified by recrystallization, making it well-suited for iterative synthesis in medicinal chemistry and process development workflows.

Synthesis

  • Route1
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      598-21-0
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      74497-02-2
    • ~80%
    • In-stock
      2-Bromo-N-phenylacetamide|CS-D0368
      5326-87-4

    References

    • Samanta, Sanjay; Lim, Ting Liang; Lam, Yulin ChemMedChem, 2013 , vol. 8, # 6 p. 994 - 1001
  • Route2
    • null|null
      22118-09-8
    • null|null
      74497-02-2
    • ~87%
    • In-stock
      2-Bromo-N-phenylacetamide|CS-D0368
      5326-87-4

    References

    • Vloon; Kruk; Pandit; Hofs; McVie Journal of Medicinal Chemistry, 1987 , vol. 30, # 1 p. 20 - 24
  • Route3
    • null|null
      79-08-3
    • null|null
      74497-02-2
    • ~82%
    • In-stock
      2-Bromo-N-phenylacetamide|CS-D0368
      5326-87-4

    References

    • Smith III, Amos B.; Savinov, Sergey N.; Manjappara, Uma V.; Chaiken, Irwin M. Organic Letters, 2002 , vol. 4, # 23 p. 4041 - 4044

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS05,GHS07
Signal Word : Danger
UN#: 3261
Class : 8
Packing Group : Ⅱ
Hazard Statements : H302-H314
Precautionary Statements : P260-P264-P270-P280-P301+P330+P331-P304+P340-P363-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   29.1
  • LogP   2.02
  • H_Acceptors   1
  • H_Donors   1
  • Rotatable_Bonds   2

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