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CS-W001157 4
Total: USD 88.00

5-Bromo-3-methylbenzo[d]isoxazole

  • CAS No. 66033-76-9

  • Cat. No. CS-D0883
  • Purity≥96%
  • MDL No.MFCD08669459

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

5-Bromo-3-methylbenzo[d]isoxazole|CS-D0883

Structure of 66033-76-9

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General Information

  • CAS No. 66033-76-9
  • Cat. No. CS-D0883
  • Purity ≥96%
  • MDL No. MFCD08669459
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₆BrNO
  • Molecular Weight 212.04
  • Synonym(s) 5-BroMo-3-Methyl-1,2-benzoxazole
  • SMILES CC1=NOC2=C1C=C(Br)C=C2

Description

5-Bromo-3-methylbenzo[d]isoxazole is a heteroaromatic scaffold featuring a bromine substituent and a methyl group at regioselective positions, enabling direct functionalization in cross-coupling reactions. This bench-stable, moisture-tolerant compound integrates readily into complex molecular architectures, serving as a key building block for bioactive molecule synthesis.

Application

5-Bromo-3-methylbenzo[d]isoxazole serves as a versatile building block for the synthesis of bioactive heterocycles, enabling palladium-catalyzed cross-coupling reactions with high functional group tolerance. The bromo substituent facilitates Suzuki, Stille, and Negishi couplings, while the methyl group enhances metabolic stability in downstream pharmaceutical scaffolds. Its bench-stable crystalline form simplifies handling and purification in multi-step synthetic sequences.

Synthesis

  • Route1
    • null|null
      1416157-63-5
    • ~66%
    • In-stock
      5-Bromo-3-methylbenzo[d]isoxazole|CS-D0883
      66033-76-9

    References

    • Cystic Fibrosis Foundation Therapeutics, Inc. Patent: US8334292 B1, 2012 ; Location in patent: Page/Page column 55 ; US 8334292 B1
  • Route2
    • null|null
      92832-02-5
    • ~89%
    • In-stock
      5-Bromo-3-methylbenzo[d]isoxazole|CS-D0883
      66033-76-9

    References

    • Chen, Cheng-Yi; Andreani, Teresa; Li, Hongmei Organic Letters, 2011 , vol. 13, # 23 p. 6300 - 6303
  • Route3
    • null|null
      1215858-74-4
    • ~66%
    • In-stock
      5-Bromo-3-methylbenzo[d]isoxazole|CS-D0883
      66033-76-9

    References

    • Udd, Sandra; Jokela, Reija; Franzen, Robert; Tois, Jan Tetrahedron Letters, 2010 , vol. 51, # 7 p. 1030 - 1033

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

Quality Control

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Computational Chemistry Data

  • TPSA   26.03
  • LogP   2.89872
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   0

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