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9-Bromoacridine

  • CAS No. 4357-57-7

  • Cat. No. CS-0255162
  • Purity≥97%
  • MDL No.None

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

9-Bromoacridine|CS-0255162

Structure of 4357-57-7

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General Information

  • CAS No. 4357-57-7
  • Cat. No. CS-0255162
  • Purity ≥97%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₃H₈BrN
  • Molecular Weight 258.11
  • Synonym(s) Acridine,9-bromo
  • SMILES BrC1=C(C=CC=C2)C2=NC3=CC=CC=C31

Description

9-Bromoacridine is a brominated acridine derivative featuring a planar, electron-rich heteroaromatic core. This structure enables effective DNA intercalation and fluorescence enhancement in biological labeling applications. The bromine substituent facilitates further functionalization via palladium-catalyzed coupling reactions. Bench-stable and soluble in common organic solvents, it serves as a robust scaffold for probe development.

Application

9-Bromoacridine serves as a versatile building block in synthetic organic chemistry, enabling palladium-catalyzed cross-coupling reactions for the construction of biaryl scaffolds. Its bromine substituent provides high reactivity in Suzuki, Stille, and Negishi couplings, while the acridine core offers inherent stability and fluorescence utility. The compound exhibits excellent bench stability and facilitates straightforward purification, making it well-suited for applications in medicinal chemistry and materials science.

Synthesis

  • Route1

    References

    • Kawai, Hidetoshi; Takeda, Takashi; Fujiwara, Kenshu; Suzuki, Takanori Journal of the American Chemical Society, 2005 , vol. 127, # 35 p. 12172 - 12173
  • Route2
    • Thio-acridone|CS-1297598
      6540-78-9
    • ~%
    • In-stock
      9-Bromoacridine|CS-0255162
      4357-57-7

    References

    • Edinger; Arnold Journal fuer Praktische Chemie (Leipzig), 1901 , vol. <2> 64, p. 471 Full Text Show Details Edinger Chemische Berichte, 1900 , vol. 33, p. 3770 Full Text Show Details Kalle and Co. Patent: DE122607 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 6, p. 492
  • Route3
    • Acridone Oxcarbazepine Impurity|CS-0228810
      578-95-0
    • ~%
    • In-stock
      9-Bromoacridine|CS-0255162
      4357-57-7

    References

    • Singer, Berndt; Maas, Gerhard Zeitschrift fuer Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1984 , vol. 39, # 10 p. 1399 - 1408

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS05,GHS06
Signal Word : Danger
UN#: 2811
Class : 6.1
Packing Group : Ⅲ
Hazard Statements : H301-H315-H318-H335-H413
Precautionary Statements : P261-P264-P270-P271-P273-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   12.89
  • LogP   4.1505
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   0

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