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CS-W001157 4
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4-(3-(Trifluoromethyl)-3H-diazirin-3-yl)benzaldehyde

  • CAS No. 128886-88-4

  • Cat. No. CS-0008637
  • Purity≥95%
  • MDL No.MFCD22683681

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

4-(3-(Trifluoromethyl)-3H-diazirin-3-yl)benzaldehyde|CS-0008637

Structure of 128886-88-4

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General Information

  • CAS No. 128886-88-4
  • Cat. No. CS-0008637
  • Purity ≥95%
  • MDL No. MFCD22683681
  • Storage -20°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₅F₃N₂O
  • Molecular Weight 214.14
  • Synonym(s) 4-[3-(trifluoromethyl)diazirin-3-yl]benzaldehyde
  • SMILES O=CC1=CC=C(C2(C(F)(F)F)N=N2)C=C1

Description

This trifluoromethyl-substituted diazirine aldehyde integrates a photoreactive diazirine ring with an electron-deficient aromatic system, enabling site-specific protein crosslinking upon UV irradiation. The para-aldelyde functionality supports direct conjugation to biomolecules via reductive amination or hydrazone formation, while the trifluoromethyl group enhances metabolic stability and modulates electronic properties for efficient photoactivation.

Application

4-(3-(Trifluoromethyl)-3H-diazirin-3-yl)benzaldehyde serves as a versatile photoreactive building block for covalent labeling and cross-linking applications. The trifluoromethyl-substituted diazirine ring enables efficient photoactivation under UV light, facilitating irreversible attachment to proximal biomolecules. The aldehyde functionality provides a site for conjugation via reductive amination or hydrazone formation, enabling site-specific probe integration. Its bench-stable nature and compatibility with diverse functional groups make it suitable for synthetic workflows in chemical biology and target identification.

Synthesis

  • Route1
    • null|null
      4885-02-3
    • In-stock
      3-Phenyl-3-(trifluoromethyl)-3H-diazirine|CS-0008636
      73899-14-6
    • ~81%
    • In-stock
      4-(3-(Trifluoromethyl)-3H-diazirin-3-yl)benzaldehyde|CS-0008637
      128886-88-4

    References

    • Nakashima, Hiroyuki; Hashimoto, Makoto; Sadakane, Yutaka; Tomohiro, Takenori; Hatanaka, Yasumaru Journal of the American Chemical Society, 2006 , vol. 128, # 47 p. 15092 - 15093
  • Route2
    • null|null
      149183-55-1
    • ~99%
    • In-stock
      4-(3-(Trifluoromethyl)-3H-diazirin-3-yl)benzaldehyde|CS-0008637
      128886-88-4

    References

    • Delfino, Jose M.; Schreiber, Stuart L.; Richards, Frederic M. Journal of the American Chemical Society, 1993 , vol. 115, # 9 p. 3458 - 3474
  • Route3

    References

    • Resek; Bhattacharya; Khorana Journal of Organic Chemistry, 1993 , vol. 58, # 26 p. 7598 - 7601

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS02,GHS05
Signal Word : Danger
UN#: 2924
Class : 3,8
Packing Group : Ⅱ
Hazard Statements : H226-H314
Precautionary Statements : P210-P240-P242-P243-P264-P271-P280-P301+P330+P331-P304+P340-P363-P370+P378-P501

Quality Control

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Computational Chemistry Data

  • TPSA   41.79
  • LogP   2.68
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   2

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