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CS-W001157 4
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1-Bromonaphthalen-2-amine

  • CAS No. 20191-75-7

  • Cat. No. CS-0135297
  • Purity≥96%
  • MDL No.None

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

1-Bromonaphthalen-2-amine|CS-0135297

Structure of 20191-75-7

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General Information

  • CAS No. 20191-75-7
  • Cat. No. CS-0135297
  • Purity ≥96%
  • MDL No. None
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₈BrN
  • Molecular Weight 222.08
  • Synonym(s) 2-amino-1-bromonaphthalin
  • SMILES NC1=CC=C2C=CC=CC2=C1Br

Description

1-Bromonaphthalen-2-amine features a bromine atom at the 1-position and an amino group at the 2-position of the naphthalene core, enabling direct functionalization in cross-coupling reactions. This electron-rich scaffold integrates readily into complex molecular architectures under standard conditions.

Application

1-Bromonaphthalen-2-amine serves as a versatile building block in synthetic organic chemistry, enabling palladium-catalyzed cross-coupling reactions such as Suzuki-Miyaura and Buchwald-Hartwig couplings. Its bromo group facilitates efficient functionalization at the naphthalene C1 position, while the ortho-amino functionality supports direct metallation or incorporation into heterocyclic scaffolds. The compound exhibits good bench stability and is compatible with standard purification protocols, making it a practical choice for medicinal chemistry and materials synthesis workflows.

Synthesis

  • Route1
    • null|null
      91-59-8
    • ~97%
    • In-stock
      1-Bromonaphthalen-2-amine|CS-0135297
      20191-75-7

    References

    • Venkateswarlu, Katta; Suneel, Kanaparthy; Das, Biswanath; Reddy, Kuravallapalli Nagabhushana; Reddy, Thummala Sreenivasulu Synthetic Communications, 2009 , vol. 39, # 2 p. 215 - 219
  • Route2
    • null|null
      612-52-2
    • ~%
    • In-stock
      1-Bromonaphthalen-2-amine|CS-0135297
      20191-75-7

    References

    • Jin, Wei; Trzupek, John D.; Rayl, Thomas J.; Broward, Melinda A.; Vielhauer, George A.; Weir, Scott J.; Hwang, Inkyu; Boger, Dale L. Journal of the American Chemical Society, 2007 , vol. 129, # 49 p. 15391 - 15397
  • Route3
    • N-(Naphthalen-2-yl)acetamide|CS-W016951
      581-97-5
    • ~%
    • In-stock
      1-Bromonaphthalen-2-amine|CS-0135297
      20191-75-7

    References

    • Makosza, Mieczyslaw; Ostrowski, Stanislaw Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1991 , p. 1093 - 1097

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS08
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H312-H315-H319-H332-H335-H351-H412
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362-P405-P501

Quality Control

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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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