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CS-W001157 4
Total: USD 88.00

2-Amino-6-bromophenol

  • CAS No. 28165-50-6

  • Cat. No. CS-W004671
  • Purity≥98%
  • MDL No.MFCD08277300

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

2-Amino-6-bromophenol|CS-W004671

Structure of 28165-50-6

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General Information

  • CAS No. 28165-50-6
  • Cat. No. CS-W004671
  • Purity ≥98%
  • MDL No. MFCD08277300
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₆BrNO
  • Molecular Weight 188.02
  • Synonym(s) 3-BROMO-2-HYDROXYANILINE
  • SMILES OC1=C(Br)C=CC=C1N

Description

2-Amino-6-bromophenol features a bromine atom at the para position relative to a hydroxyl group, delivering high reactivity for coupling reactions. The amino group enhances electron density, enabling efficient participation in electrophilic substitutions and metal-catalyzed transformations. This bench-stable compound serves as a key intermediate in the synthesis of functionalized heterocycles and bioactive molecules.

Application

2-Amino-6-bromophenol serves as a versatile building block in medicinal chemistry and materials synthesis, enabling direct access to substituted heterocycles via cyclization or coupling reactions. Its ortho-directed reactivity facilitates regioselective functionalization, while the amino and phenolic groups offer complementary handles for derivatization. The compound exhibits good bench stability and is readily purified by recrystallization, supporting efficient integration into multi-step synthetic sequences.

Synthesis

  • Route1

    References

    • Costales, Abran; Mathur, Michelle; Ramurthy, Savithri; Lan, Jiong; Subramanian, Sharadha; Jain, Rama; Atallah, Gordana; Setti, Lina; Lindvall, Mika; Appleton, Brent A.; Ornelas, Elizabeth; Feucht, Paul; Warne, Bob; Doyle, Laura; Basham, Stephen E.; Aronchik, Ida; Jefferson, Anne B.; Shafer, Cynthia M. Bioorganic and Medicinal Chemistry Letters, 2014 , vol. 24, # 6 p. 1592 - 1596
  • Route2
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    • In-stock
      2-Amino-6-bromophenol|CS-W004671
      28165-50-6

    References

    • Zhao, Shu-Hai; Berger, Jacob; Clark, Robin D.; Sethofer, Steven G.; Krauss, Nancy E.; Brothers, Julie M.; Martin, Renee S.; Misner, Dinah L.; Schwab, Dietmar; Alexandrova, Ludmila Bioorganic and Medicinal Chemistry Letters, 2007 , vol. 17, # 12 p. 3504 - 3507
  • Route3

    References

    • Novak, Michael; Rovin, Lise H.; Pelecanou, Maria; Mulero, Julio J.; Lagerman, Robert K. Journal of Organic Chemistry, 1987 , vol. 52, # 10 p. 2002 - 2010

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07,GHS09
Signal Word : Warning
UN#: 3077
Class : 9
Packing Group : Ⅲ
Hazard Statements : H302-H410
Precautionary Statements : P264-P270-P273-P330-P391-P501

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Computational Chemistry Data

  • TPSA   46.25
  • LogP   1.7369
  • H_Acceptors   2
  • H_Donors   2
  • Rotatable_Bonds   0

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