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CS-W001157 4
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N-(5-Bromopentyl)phthalimide

  • CAS No. 954-81-4

  • Cat. No. CS-0019374
  • Purity≥97%
  • MDL No.MFCD00060522

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

N-(5-Bromopentyl)phthalimide|CS-0019374

Structure of 954-81-4

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General Information

  • CAS No. 954-81-4
  • Cat. No. CS-0019374
  • Purity ≥97%
  • MDL No. MFCD00060522
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₃H₁₄BrNO₂
  • Molecular Weight 296.16
  • Synonym(s) N-(5-Bromopentyl)phthalamide; 2-(5-bromopentyl)-2,3-dihydro-1H-isoindole-1,3-di one
  • SMILES O=C1N(CCCCCBr)C(C2=C1C=CC=C2)=O

Description

N-(5-Bromopentyl)phthalimide features a brominated alkyl chain tethered to the nitrogen of phthalimide, enabling efficient conjugation in synthetic workflows. This electrophilic handle facilitates nucleophilic substitution reactions under mild conditions, offering a reliable route to functionalized derivatives for medicinal chemistry and polymer synthesis.

Application

N-(5-Bromopentyl)phthalimide serves as a versatile bifunctional building block in synthetic organic chemistry, enabling efficient introduction of both phthalimido and alkyl bromide moieties. The bromide group facilitates nucleophilic substitution reactions, while the phthalimide acts as a robust nitrogen protecting group. Its stability under standard reaction conditions and compatibility with diverse functional groups make it particularly useful for synthesizing heterocyclic scaffolds and peptide analogs via straightforward alkylation protocols.

Synthesis

  • Route1
    • null|null
      85-44-9
    • ~%
    • In-stock
      N-(5-Bromopentyl)phthalimide|CS-0019374
      954-81-4

    References

    • Synthetic Communications, , vol. 15, # 14 p. 1277 - 1290
  • Route2
    • null|null
      111-24-0
    • null|null
      1074-82-4
    • ~73%
    • In-stock
      N-(5-Bromopentyl)phthalimide|CS-0019374
      954-81-4

    References

    • Ignasik, Michalina; Bajda, Marek; Guzior, Natalia; Prinz, Michaela; Holzgrabe, Ulrike; Malawska, Barbara Archiv der Pharmazie, 2012 , vol. 345, # 7 p. 509 - 516
  • Route3
    • null|null
      136918-14-4
    • null|null
      111-24-0
    • ~78%
    • In-stock
      N-(5-Bromopentyl)phthalimide|CS-0019374
      954-81-4

    References

    • Constant; Carden; Lhomme Journal of Heterocyclic Chemistry, 1985 , vol. 22, # 4 p. 1035 - 1040

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07,GHS09
Signal Word : Warning
UN#: 3077
Class : 9
Packing Group : Ⅲ
Hazard Statements : H302-H315-H317-H319-H335-H410
Precautionary Statements : P261-P264-P270-P271-P272-P273-P280-P302+P352-P304+P340-P330-P362+P364-P391-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   37.38
  • LogP   2.8478
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   5

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