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4-Nitro-2-amino-1-ethylbenzene

  • CAS No. 20191-74-6

  • Cat. No. CS-0012535
  • Purity≥96%
  • MDL No.MFCD00034056

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

4-Nitro-2-amino-1-ethylbenzene|CS-0012535

Structure of 20191-74-6

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General Information

  • CAS No. 20191-74-6
  • Cat. No. CS-0012535
  • Purity ≥96%
  • MDL No. MFCD00034056
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₁₀N₂O₂
  • Molecular Weight 166.18
  • Synonym(s) Aniline, 2-ethyl-5-nitro- ; 2-Ethyl-5-nitroaniline; 2-Ethyl-5-nitrobenzenamine; Pazopanib Impurity 53
  • SMILES CCC1=CC=C([N+]([O-])=O)C=C1N

Description

4-Nitro-2-amino-1-ethylbenzene features a para-nitro group and ortho-amino functionality on an ethyl-substituted benzene ring, enabling dual reactivity in coupling and functionalization processes. This electron-deficient scaffold integrates readily into complex molecular architectures under standard conditions.

Application

4-Nitro-2-amino-1-ethylbenzene serves as a versatile building block for the synthesis of functionalized aromatic scaffolds, enabling direct access to substituted anilines and heterocycles via standard coupling and cyclization protocols. The ortho-amino and para-nitro groups offer complementary reactivity for sequential transformations, while the ethyl substituent enhances solubility and modulates electronic effects. Its bench-stable nature and compatibility with common reaction conditions facilitate efficient purification and integration into multi-step syntheses.

Synthesis

  • Route1
    • null|null
      578-54-1
    • ~58%
    • In-stock
      4-Nitro-2-amino-1-ethylbenzene|CS-0012535
      20191-74-6

    References

    • Harris, Philip A.; Boloor, Amogh; Cheung, Mui; Kumar, Rakesh; Crosby, Renae M.; Davis-Ward, Ronda G.; Epperly, Andrea H.; Hinkle, Kevin W.; Hunter III, Robert N.; Johnson, Jennifer H.; Knick, Victoria B.; Laudeman, Christopher P.; Luttrell, Deirdre K.; Mook, Robert A.; Nolte, Robert T.; Rudolph, Sharon K.; Szewczyk, Jerzy R.; Truesdale, Anne T.; Veal, James M.; Wang, Liping; Stafford, Jeffrey A. Journal of Medicinal Chemistry, 2008 , vol. 51, # 15 p. 4632 - 4640
  • Route2
    • 1-Ethyl-2,4-dinitrobenzene|CS-0585791
      1204-29-1
    • ~49%
    • In-stock
      4-Nitro-2-amino-1-ethylbenzene|CS-0012535
      20191-74-6

    References

    • AMGEN INC.; MEMORY PHARMACEUTICALS CORPORATION Patent: WO2007/103260 A1, 2007 ; Location in patent: Page/Page column 56-57 ; WO 2007/103260 A1
  • Route3
    • N-(2-ethylphenyl)acetamide|CS-0316169
      33098-65-6
    • ~%
    • 2-Ethyl-4-nitroaniline|CS-0312404
      6853-29-8
    • In-stock
      4-Nitro-2-amino-1-ethylbenzene|CS-0012535
      20191-74-6

    References

    • US2013/178460 A1, ; Page/Page column 0169 ;

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   69.16
  • LogP   1.7394
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   2

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