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CS-W001157 4
Total: USD 88.00

6-Bromo-2-methylbenzodoxazole

  • CAS No. 151230-42-1

  • Cat. No. CS-0006594
  • Purity≥97%
  • MDL No.MFCD06659628

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

6-Bromo-2-methylbenzodoxazole|CS-0006594

Structure of 151230-42-1

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General Information

  • CAS No. 151230-42-1
  • Cat. No. CS-0006594
  • Purity ≥97%
  • MDL No. MFCD06659628
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₆BrNO
  • Molecular Weight 212.04
  • Synonym(s) 6-Bromo-2-methylbenzo[d]oxazole
  • SMILES CC1=NC2=CC=C(Br)C=C2O1

Description

6-Bromo-2-methylbenzoxazole is a halogenated heterocyclic scaffold featuring a bromine atom at the 6-position and a methyl group at the 2-position. This electron-deficient benzoxazole derivative exhibits enhanced reactivity in palladium-catalyzed cross-coupling reactions, enabling efficient C–C bond formation under standard conditions. The steric profile of the methyl substituent improves regioselectivity, while the bromine moiety serves as a reliable coupling handle. This compound functions effectively as a building block in medicinal chemistry and materials science applications.

Application

6-Bromo-2-methylbenzoxazole serves as a versatile heterocyclic building block in medicinal chemistry and materials science. Its bromine substituent enables palladium-catalyzed cross-coupling reactions, while the methyl group enhances lipophilicity and metabolic stability. The benzoxazole core provides rigidity and improved binding affinity in target-directed synthesis. This compound exhibits excellent bench stability, ease of purification, and compatibility with standard synthetic workflows.

Synthesis

  • Route1
    • null|null
      1445-45-0
    • In-stock
      2-Amino-5-bromophenol|CS-W003015
      38191-34-3
    • ~82%
    • In-stock
      6-Bromo-2-methylbenzodoxazole|CS-0006594
      151230-42-1

    References

    • US2012/253040 A1, ; Page/Page column 31 ;
  • Route2
    • In-stock
      2-Amino-5-bromophenol|CS-W003015
      38191-34-3
    • null|null
      78-39-7
    • ~63%
    • In-stock
      6-Bromo-2-methylbenzodoxazole|CS-0006594
      151230-42-1

    References

    • WO2012/151525 A1, ; Page/Page column 128 ; WO 2012/151525 A1
  • Route3
    • null|null
      16394-40-4
    • ~77%
    • In-stock
      6-Bromo-2-methylbenzodoxazole|CS-0006594
      151230-42-1

    References

    • Monatshefte fuer Chemie, , vol. 124, # 4 p. 367 - 380

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS05,GHS07
Signal Word : Danger
UN#: 1759
Class : 8
Packing Group : Ⅲ
Hazard Statements : H302-H315-H318-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-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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