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CS-W001157 4
Total: USD 88.00

4-Amino-3-bromophenol

  • CAS No. 74440-80-5

  • Cat. No. CS-0042863
  • Purity≥95%
  • MDL No.MFCD09966089

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

4-Amino-3-bromophenol|CS-0042863

Structure of 74440-80-5

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General Information

  • CAS No. 74440-80-5
  • Cat. No. CS-0042863
  • Purity ≥95%
  • MDL No. MFCD09966089
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₆BrNO
  • Molecular Weight 188.02
  • Synonym(s) None
  • SMILES NC1=C(Br)C=C(O)C=C1

Description

4-Amino-3-bromophenol features a bromine substituent at the meta position relative to the hydroxyl group, enabling selective functionalization in synthetic sequences. The electron-donating amino group enhances reactivity at adjacent sites, while the phenolic OH facilitates hydrogen bonding and solubility in polar solvents. This compound serves as a key intermediate in pharmaceutical and agrochemical synthesis.

Application

4-Amino-3-bromophenol serves as a versatile building block in medicinal chemistry, enabling direct access to substituted anilines and heterocyclic scaffolds via standard coupling reactions. Its ortho-bromo and amino groups offer complementary reactivity for palladium-catalyzed cross-couplings and electrophilic substitutions, while the phenolic hydroxyl supports derivatization or protection strategies. The compound exhibits good bench stability and facilitates straightforward purification, making it well-suited for iterative synthesis workflows in API development.

Synthesis

  • Route1

    References

    • Parker, Kathlyn A.; Mindt, Thomas L. Organic Letters, 2002 , vol. 4, # 24 p. 4265 - 4268
  • Route2
    • null|null
      123-30-8
    • ~95%
    • In-stock
      4-Amino-3-bromophenol|CS-0042863
      74440-80-5

    References

    • Boruah, Jeena Jyoti; Das, Siva Prasad; Borah, Rupam; Gogoi, Sandhya Rani; Islam, Nashreen S. Polyhedron, 2013 , vol. 52, p. 246 - 254
  • Route3
    • null|null
      577-19-5
    • ~%
    • In-stock
      4-Amino-3-bromophenol|CS-0042863
      74440-80-5

    References

    • le Guyader,M. Bulletin de la Societe Chimique de France, 1966 , p. 1848 - 1858

Safety Information

Download SDS
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-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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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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