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CS-W001157 4
Total: USD 88.00

3-(4-(bromomethyl)phenyl)-3-(trifluoromethyl)-3H-diazirine

  • CAS No. 92367-11-8

  • Cat. No. CS-0008639
  • Purity≥95%
  • MDL No.MFCD19442581

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

3-(4-(bromomethyl)phenyl)-3-(trifluoromethyl)-3H-diazirine|CS-0008639

Structure of 92367-11-8

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General Information

  • CAS No. 92367-11-8
  • Cat. No. CS-0008639
  • Purity ≥95%
  • MDL No. MFCD19442581
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₆BrF₃N₂
  • Molecular Weight 279.06
  • Synonym(s) 4-[3-(Trifluoromethyl)-3H-diazirin-3-yl]benzyl Bromide
  • SMILES FC(C1(C2=CC=C(CBr)C=C2)N=N1)(F)F

Description

This diazirine derivative features a bromomethyl group flanking a trifluoromethyl-substituted aromatic ring, enabling efficient photoaffinity labeling. The electron-deficient diazirine moiety integrates readily into bioconjugation workflows under standard conditions.

Application

3-(4-(Bromomethyl)phenyl)-3-(trifluoromethyl)-3H-diazirine serves as a versatile photoaffinity labeling probe, enabling site-specific protein crosslinking upon UV irradiation. The trifluoromethyl group enhances metabolic stability and lipophilicity, while the bromomethyl moiety facilitates downstream conjugation via nucleophilic substitution. Its bench-stable crystalline form and compatibility with standard synthetic workflows make it ideal for probing biomolecular interactions in drug discovery and chemical biology applications.

Synthesis

  • Route1

    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
    • 3-(P-tolyl)-3-(trifluoromethyl)-3h-diazirine|CS-0874787
      87736-85-4
    • ~88%
    • In-stock
      3-(4-(bromomethyl)phenyl)-3-(trifluoromethyl)-3H-diazirine|CS-0008639
      92367-11-8

    References

    • Latli, Bachir; Morimoto, Hiromi; Williams, Philip G.; Casida, John E. Journal of Labelled Compounds and Radiopharmaceuticals, 1998 , vol. 41, # 3 p. 191 - 199
  • Route3
    • null|null
      13057-17-5
    • In-stock
      3-Phenyl-3-(trifluoromethyl)-3H-diazirine|CS-0008636
      73899-14-6
    • ~28%
    • In-stock
      3-(4-(bromomethyl)phenyl)-3-(trifluoromethyl)-3H-diazirine|CS-0008639
      92367-11-8

    References

    • Nakashima, Hiroyuki; Hashimoto, Makoto; Sadakane, Yutaka; Tomohiro, Takenori; Hatanaka, Yasumaru Journal of the American Chemical Society, 2006 , vol. 128, # 47 p. 15092 - 15093

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-P233-P240-P241-P242-P243-P260-P264-P280-P301+P330+P331-P304+P340-P363-P370+P378-P405-P501

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Computational Chemistry Data

  • TPSA   24.72
  • LogP   3.7624
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   2

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