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CS-W001157 4
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2-(Oxiran-2-ylmethyl)isoindoline-1,3-dione

  • CAS No. 5455-98-1

  • Cat. No. CS-0020844
  • Purity≥95%
  • MDL No.MFCD00005896

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

2-(Oxiran-2-ylmethyl)isoindoline-1,3-dione|CS-0020844

Structure of 5455-98-1

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General Information

  • CAS No. 5455-98-1
  • Cat. No. CS-0020844
  • Purity ≥95%
  • MDL No. MFCD00005896
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₉NO₃
  • Molecular Weight 203.19
  • Synonym(s) N-Glycidyphthalimide
  • SMILES O=C1C2=C(C(N1CC3OC3)=O)C=CC=C2

Description

This oxirane-functional isoindoline derivative integrates a reactive epoxide ring with a rigid, electron-deficient isoindoline scaffold. The strained oxirane moiety enables selective nucleophilic ring opening under mild conditions, facilitating conjugation to amines or thiols in bioconjugation workflows. Designed for stability during storage and ease of handling, this compound serves as a robust linker in the synthesis of targeted therapeutics and functionalized polymers.

Application

2-(Oxiran-2-ylmethyl)isoindoline-1,3-dione serves as a versatile bifunctional building block, enabling efficient construction of complex heterocyclic scaffolds. The epoxide moiety facilitates regioselective ring-opening reactions with nucleophiles, while the phthalimide group offers excellent stability and compatibility with standard synthetic protocols. Its bench-stable nature and predictable reactivity make it ideal for modular synthesis in medicinal chemistry and process development workflows.

Synthesis

  • Route1
    • null|null
      1074-82-4
    • null|null
      3132-64-7
    • ~51%
    • In-stock
      2-(Oxiran-2-ylmethyl)isoindoline-1,3-dione|CS-0020844
      5455-98-1

    References

    • Kirin Beer Kabushiki Kaisha Patent: US6875884 B1, 2005 ; Location in patent: Page/Page column 26; 203-204 ; US 6875884 B1
  • Route2
    • null|null
      1074-82-4
    • null|null
      106-89-8
    • ~92%
    • In-stock
      2-(Oxiran-2-ylmethyl)isoindoline-1,3-dione|CS-0020844
      5455-98-1

    References

    • Meyer, Joerg; Keul, Helmut; Moeller, Martin Macromolecules, 2011 , vol. 44, # 11 p. 4082 - 4091
  • Route3

    References

    • Carruthers, Nicholas I.; Spitler, James M.; Wong, Shing-Chun; Blythin, David J.; Chen, Xiao; Shue, Ho-Jane; She, Hoyan S.; Lee, Joe F.; Rizzo, Charles; Ting, Pauline C.; West Jr., Robert E. Bioorganic and Medicinal Chemistry Letters, 1998 , vol. 8, # 21 p. 3059 - 3064

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS05
Signal Word : Danger
UN#: 3261
Class : 8
Packing Group : Ⅲ
Hazard Statements : H318
Precautionary Statements : P260-P264-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P363-P405-P501

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Computational Chemistry Data

  • TPSA   49.91
  • LogP   0.6814
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   2

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