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CS-W001157 4
Total: USD 88.00

3-Amino-4-nitrophenol

  • CAS No. 16292-90-3

  • Cat. No. CS-0018956
  • Purity≥98%
  • MDL No.MFCD13185928

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

3-Amino-4-nitrophenol|CS-0018956

Structure of 16292-90-3

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General Information

  • CAS No. 16292-90-3
  • Cat. No. CS-0018956
  • Purity ≥98%
  • MDL No. MFCD13185928
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₆N₂O₃
  • Molecular Weight 154.12
  • Synonym(s) 1,1'-(1,4-Phenylene)bis[3-(2-chloroethyl)urea]
  • SMILES OC1=CC=C([N+]([O-])=O)C(N)=C1

Description

3-Amino-4-nitrophenol delivers a strategically positioned amino group adjacent to a nitro functionality, enabling direct conjugation in dye synthesis and pharmaceutical intermediates. This electron-deficient phenolic scaffold supports controlled reactivity under standard conditions, integrating readily into complex molecular architectures with predictable regiochemistry.

Application

3-Amino-4-nitrophenol serves as a versatile building block in medicinal chemistry and materials science, enabling the synthesis of heterocyclic scaffolds and functional dyes. Its ortho-dipolar functionality facilitates direct coupling reactions and regioselective derivatization under mild conditions. The compound exhibits sufficient bench stability for routine handling and is compatible with common protecting group strategies, making it well-suited for multi-step synthetic sequences requiring precise nitrogen and oxygen reactivity control.

Synthesis

  • Route1

    References

    • Imoto, Mitsutaka; Matsui, Yasunori; Takeda, Motonori; Tamaki, Akihiro; Taniguchi, Hisaji; Mizuno, Kazuhiko; Ikeda, Hiroshi Journal of Organic Chemistry, 2011 , vol. 76, # 15 p. 6356 - 6361
  • Route2
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      3-Amino-4-nitrophenol|CS-0018956
      16292-90-3

    References

    • Meldola; Stephens Journal of the Chemical Society, 1906 , vol. 89, p. 924
  • Route3
    • 3-Acetamidophenyl acetate|CS-0061069
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      3-Amino-4-nitrophenol|CS-0018956
      16292-90-3

    References

    • Meldola; Stephens Journal of the Chemical Society, 1906 , vol. 89, p. 924

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

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Computational Chemistry Data

  • TPSA   89.39
  • LogP   0.8826
  • H_Acceptors   4
  • H_Donors   2
  • Rotatable_Bonds   1

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