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CS-W001157 4
Total: USD 88.00

2-Hydroxy-3-nitrobenzonitrile

  • CAS No. 28177-79-9

  • Cat. No. CS-0102183
  • Purity≥96%
  • MDL No.MFCD00234257

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

2-Hydroxy-3-nitrobenzonitrile|CS-0102183

Structure of 28177-79-9

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General Information

  • CAS No. 28177-79-9
  • Cat. No. CS-0102183
  • Purity ≥96%
  • MDL No. MFCD00234257
  • Storage RT, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₄N₂O₃
  • Molecular Weight 164.12
  • Synonym(s) 2-HYDROXY-3-NITRO-BENZONITRILE
  • SMILES N#CC1=CC=CC([N+]([O-])=O)=C1O

Description

2-Hydroxy-3-nitrobenzonitrile features a strategically positioned hydroxyl group flanked by electron-withdrawing nitro and nitrile functionalities, enabling its use in constructing complex heterocycles. This ortho-substituted scaffold offers enhanced reactivity in coupling processes under standard conditions.

Application

2-Hydroxy-3-nitrobenzonitrile serves as a versatile building block in synthetic organic chemistry, enabling the construction of substituted heterocycles and functionalized aromatic scaffolds. Its ortho-directed reactivity facilitates efficient cyclizations and metal-catalyzed couplings. The molecule exhibits good bench stability, tolerates common functional groups, and simplifies purification due to its crystalline nature and distinct polarity profile.

Synthesis

  • Route1

    References

    • SmithKline Beecham Corporation Patent: US6248785 B1, 2001 ; US 6248785 B1
  • Route2

    References

    • BOEHRINGER INGELHEIM PHARMA GMBH and CO. KG Patent: WO2004/39764 A1, 2004 ; Location in patent: Page/Page column 88 ; WO 2004/039764 A1
  • Route3
    • null|null
      151-50-8
    • null|null
      528-29-0
    • ~4%
    • In-stock
      2,2'-Oxybis(nitrobenzene)|CS-0018713
      2217-65-4
    • In-stock
      2-Hydroxy-3-nitrobenzonitrile|CS-0102183
      28177-79-9
    • null|null
      88-75-5

    References

    • Gorvin, John H. Journal of Chemical Research, Miniprint, 1991 , # 4 p. 738 - 762

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
Precautionary Statements : P264-P270-P330-P501

Quality Control

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Computational Chemistry Data

  • TPSA   87.16
  • LogP   1.17208
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   1

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