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8-Bromonaphthalen-1-amine

  • CAS No. 62456-34-2

  • Cat. No. CS-0131601
  • Purity≥97%
  • MDL No.MFCD01860254

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

8-Bromonaphthalen-1-amine|CS-0131601

Structure of 62456-34-2

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General Information

  • CAS No. 62456-34-2
  • Cat. No. CS-0131601
  • Purity ≥97%
  • MDL No. MFCD01860254
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₈BrN
  • Molecular Weight 222.08
  • Synonym(s) 8-Bromo-phthalen-1-ylamine
  • SMILES NC1=C2C(Br)=CC=CC2=CC=C1

Description

8-Bromonaphthalen-1-amine features a bromine substituent at the 8-position of the naphthalene core, enhancing electrophilic reactivity and enabling direct functionalization in cross-coupling processes. This bench-stable derivative integrates readily into synthetic pathways requiring halogen-directed C–H activation or transition-metal-mediated transformations.

Application

8-Bromonaphthalen-1-amine serves as a versatile building block in synthetic organic chemistry, enabling palladium-catalyzed cross-coupling reactions and facilitating the construction of biologically relevant naphthalene-based scaffolds. The bromo group provides high reactivity in Suzuki, Stille, and Negishi couplings, while the primary amine offers orthogonal functionality for derivatization. Its bench-stable nature and compatibility with diverse reaction conditions make it a practical choice for medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • Repine, Joseph T.; Johnson, Douglas S.; White, Andrew D.; Favor, David A.; Stier, Michael A.; Yip, Judy; Rankin, Trent; Ding, Qizhu; Maiti, Samarendra N. Tetrahedron Letters, 2007 , vol. 48, # 31 p. 5539 - 5541
  • Route2

    References

    • Noland, Wayland E.; Narina, Venkata Srinivasarao; Britton, Doyle Journal of Chemical Research, 2011 , vol. 35, # 12 p. 694 - 697
  • Route3

    References

    • Vyskocil, Stepan; Meca, Ludek; Tislerova, Iva; Cisarova, Ivana; Polasek, Miroslav; Harutyunyan, Syuzanna R.; Belokon, Yuri N.; Stead, Russel M. J.; Farrugia, Louis; Lockhart, Stephen C.; Mitchell, William L.; Kocovsky, Pavel Chemistry--A European Journal, 2002 , vol. 8, # 20 p. 4633 - 4648

Safety Information

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GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501

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Computational Chemistry Data

  • TPSA   26.02
  • LogP   3.1845
  • H_Acceptors   1
  • H_Donors   1
  • Rotatable_Bonds   0

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