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CS-W001157 4
Total: USD 88.00

1-(2,6-Dichloro-3-nitrophenyl)ethanone

  • CAS No. 223785-76-0

  • Cat. No. CS-0155134
  • Purity≥97%
  • MDL No.MFCD17170414

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

1-(2,6-Dichloro-3-nitrophenyl)ethanone|CS-0155134

Structure of 223785-76-0

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General Information

  • CAS No. 223785-76-0
  • Cat. No. CS-0155134
  • Purity ≥97%
  • MDL No. MFCD17170414
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₅Cl₂NO₃
  • Molecular Weight 234.04
  • Synonym(s) 2',6'-dichloro-3'-nitroacetophenone
  • SMILES CC(=O)C1=C(C=CC(=C1Cl)[N+](=O)[O-])Cl

Description

1-(2,6-Dichloro-3-nitrophenyl)ethanone features a nitro-substituted aromatic core paired with a ketone-functionalized side chain, delivering high reactivity in electrophilic coupling reactions. The electron-deficient ring enhances its utility in C–C bond formation, while the dichloro substitution pattern ensures structural rigidity and improved solubility under standard conditions.

Application

1-(2,6-Dichloro-3-nitrophenyl)ethanone serves as a versatile building block in medicinal chemistry, enabling the construction of substituted heterocycles and functionalized aryl scaffolds. Its dual electron-withdrawing groups (nitro and acetyl) enhance electrophilicity for nucleophilic aromatic substitution and facilitate downstream transformations such as reduction, coupling, and cyclization. The compound exhibits good bench stability and is amenable to standard purification techniques, making it well-suited for iterative synthesis workflows in API development.

Synthesis

  • Route1

    References

    • Breslin; Kukla; Ludovici; Mohrbacher; Ho; Miranda; Rodgers; Hitchens; Leo; Gauthier; Scott; De Clercq; Pauwels; Andries; Janssen Journal of Medicinal Chemistry, 1995 , vol. 38, # 5 p. 771 - 793

Safety Information

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GHS Pictogram :
GHS No : GHS06
Signal Word : Danger
UN#: 2810
Class : 6.1
Packing Group : Ⅲ
Hazard Statements : H301-H311-H331
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P361-P405-P501

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Computational Chemistry Data

  • TPSA   60.21
  • LogP   3.1042
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   2

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