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CS-W001157 4
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3-Bromo-5-nitroaniline

  • CAS No. 55215-57-1

  • Cat. No. CS-W021875
  • Purity≥95%
  • MDL No.MFCD00462820

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

3-Bromo-5-nitroaniline|CS-W021875

Structure of 55215-57-1

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General Information

  • CAS No. 55215-57-1
  • Cat. No. CS-W021875
  • Purity ≥95%
  • MDL No. MFCD00462820
  • Storage RT, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₅BrN₂O₂
  • Molecular Weight 217.02
  • Synonym(s) 5-Bromo-3-nitroaniline
  • SMILES NC1=CC(Br)=CC(=C1)[N+]([O-])=O

Description

3-Bromo-5-nitroaniline features a bromine substituent flanked by electron-deficient nitro and amino groups, enabling selective coupling in cross-coupling reactions. This ortho-directing arrangement supports efficient functionalization in synthetic pathways targeting bioactive heterocycles and pharmaceutical intermediates under standard conditions.

Application

3-Bromo-5-nitroaniline serves as a versatile building block in medicinal chemistry and agrochemical synthesis, enabling direct introduction of both bromo and nitro functionalities for subsequent cross-coupling or reduction reactions. Its bench-stable crystalline form facilitates handling and purification, while the ortho-directed reactivity supports selective functionalization in multi-step sequences.

Synthesis

  • Route1

    References

    • Singh, Rajinder; Tso, Kin; Zhang, Jing; Duncton, Matthew; Alvarez, Salvador; Kolluri, Rao; Ramphal, John; Holland, Sacha Patent: US2011/130415 A1, 2011 ; Location in patent: Page/Page column 75-76 ;
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      3-Bromo-5-nitroaniline|CS-W021875
      55215-57-1

    References

    • MERCK SHARP and DOHME CORP.; MERCK CANADA INC.; ALTMAN, Michael, D.; ARRINGTON, Kenneth, L.; BURCH, Jason; COTE, Bernard; FOURNIER, Jean-Francois; GAUTHIER, Jacques, Yves; KATTAR, Solomon; KNOWLES, Sandra Lee; LIM, Jongwon; MACHACEK, Michelle, R.; NORTHRUP, Alan, B.; REUTERSHAN, Michael, H.; ROBICHAUD, Joel, S.; SCHELL, Adam, J.; SPENCER, Kerrie, B. Patent: WO2011/75560 A1, 2011 ; WO 2011/075560 A1
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      96558-80-4
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    • In-stock
      3-Bromo-5-nitroaniline|CS-W021875
      55215-57-1

    References

    • Liedholm, Brita Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1984 , vol. 38, # 10 p. 877 - 884

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS05,GHS06,GHS09
Signal Word : Danger
UN#: 2811
Class : 6.1
Packing Group : Ⅲ
Hazard Statements : H301-H315-H318-H330-H335-H410
Precautionary Statements : P260-P273-P280-P284

Quality Control

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Computational Chemistry Data

  • TPSA   69.16
  • LogP   1.9395
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   1

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