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CS-W001157 4
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6-Acetylbenzo[d]oxazol-2(3H)-one

  • CAS No. 54903-09-2

  • Cat. No. CS-0181805
  • Purity≥96%
  • MDL No.MFCD01664312

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

6-Acetylbenzo[d]oxazol-2(3H)-one|CS-0181805

Structure of 54903-09-2

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General Information

  • CAS No. 54903-09-2
  • Cat. No. CS-0181805
  • Purity ≥96%
  • MDL No. MFCD01664312
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₇NO₃
  • Molecular Weight 177.16
  • Synonym(s) 6-Acetyl-2-hydroxybenzoxazole
  • SMILES O=C1OC2=CC(C(C)=O)=CC=C2N1

Description

6-Acetylbenzo[d]oxazol-2(3H)-one features a fused oxazole ring system with a ketone at the 6-position, delivering enhanced stability and solubility in polar solvents. This scaffold integrates readily into bioactive molecule design, particularly in kinase inhibitors and fluorescent probes, due to its electron-deficient heterocyclic core and reactive acetyl group enabling nucleophilic additions.

Application

6-Acetylbenzo[d]oxazol-2(3H)-one serves as a versatile heterocyclic building block in medicinal chemistry, enabling efficient access to bioactive scaffolds. Its acetyl group facilitates electrophilic functionalization and participates in classic carbonyl transformations, while the oxazolone core exhibits stability under standard reaction conditions. The compound functions effectively in coupling reactions and serves as a key intermediate in the synthesis of substituted benzoxazoles with proven utility in drug discovery workflows.

Synthesis

  • Route1
    • In-stock
      2-Benzoxazolinone|CS-W016534
      59-49-4
    • null|null
      64-19-7
    • ~61%
    • In-stock
      6-Acetylbenzo[d]oxazol-2(3H)-one|CS-0181805
      54903-09-2

    References

    • Bali, Alka; Ohri, Ruchika; Deb, Pran Kishore European Journal of Medicinal Chemistry, 2012 , vol. 49, p. 397 - 405
  • Route2
    • In-stock
      2-Benzoxazolinone|CS-W016534
      59-49-4
    • null|null
      75-36-5
    • ~69%
    • In-stock
      6-Acetylbenzo[d]oxazol-2(3H)-one|CS-0181805
      54903-09-2

    References

    • Liacha, Messaoud; Yous, Said; Poupaert, Jacques H.; Depreux, Patrick; Aichaoui, Hocine Monatshefte fur Chemie, 1999 , vol. 130, # 11 p. 1393 - 1397
  • Route3
    • In-stock
      2-Benzoxazolinone|CS-W016534
      59-49-4
    • null|null
      108-24-7
    • ~69%
    • In-stock
      6-Acetylbenzo[d]oxazol-2(3H)-one|CS-0181805
      54903-09-2

    References

    • Aichaoui, Hocine; Poupaert, Jacques H.; Lesieur, Daniel; Henichart, Jean-Pierre Tetrahedron, 1991 , vol. 47, # 33 p. 6649 - 6654 Title/Abstract Full Text View citing articles Show Details Aichaoui, Hocine; Lesieur, Daniel; Henichart, Jean-Pierre Journal of Heterocyclic Chemistry, 1992 , vol. 29, # 1 p. 171 - 175

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H315-H319
Precautionary Statements : P264-P280-P302+P352-P362+P364

Quality Control

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Computational Chemistry Data

  • TPSA   63.07
  • LogP   1.3237
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   1

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