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CS-W001157 4
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6-Bromo-1-methyl-1H-benzo[d]imidazol-2(3H)-one

  • CAS No. 305790-48-1

  • Cat. No. CS-0058751
  • Purity≥95%
  • MDL No.MFCD09759338

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

6-Bromo-1-methyl-1H-benzo[d]imidazol-2(3H)-one|CS-0058751

Structure of 305790-48-1

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General Information

  • CAS No. 305790-48-1
  • Cat. No. CS-0058751
  • Purity ≥95%
  • MDL No. MFCD09759338
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₇BrN₂O
  • Molecular Weight 227.06
  • Synonym(s) None
  • SMILES O=C1NC2=CC=C(Br)C=C2N1C

Description

6-Bromo-1-methyl-1H-benzo[d]imidazol-2(3H)-one features a brominated benzimidazolone core with a methyl group at the nitrogen, offering enhanced stability and reactivity for cross-coupling transformations. This bench-stable heterocycle serves as a key intermediate in medicinal chemistry and materials science, where its electron-deficient aromatic system facilitates selective functionalization.

Application

6-Bromo-1-methyl-1H-benzo[d]imidazol-2(3H)-one serves as a versatile building block in medicinal chemistry, enabling direct functionalization at the bromine site via Pd-catalyzed cross-coupling reactions. The methylated imidazolone core exhibits enhanced stability and solubility, facilitating purification and integration into complex heterocyclic scaffolds. Its compatibility with standard coupling protocols makes it a practical choice for constructing bioactive molecules and pharmaceutical intermediates.

Synthesis

  • Route1
    • null|null
      305790-47-0
    • ~93%
    • In-stock
      6-Bromo-1-methyl-1H-benzo[d]imidazol-2(3H)-one|CS-0058751
      305790-48-1

    References

    • Zhang, Puwen; Terefenko, Eugene A.; Wrobel, Jay; Zhang, Zhiming; Zhu, Yuan; Cohen, Jeffrey; Marschke, Keith B.; Mais, Dale Bioorganic and Medicinal Chemistry Letters, 2001 , vol. 11, # 20 p. 2747 - 2750
  • Route2
    • null|null
      77-78-1
    • tert-Butyl 5-bromo-2-oxo-2,3-dihydro-1H-benzo[d]imidazole-1-carboxylate|CS-0139084
      161468-56-0
    • ~98%
    • In-stock
      6-Bromo-1-methyl-1H-benzo[d]imidazol-2(3H)-one|CS-0058751
      305790-48-1

    References

    • AMGEN INC. Patent: WO2009/11880 A2, 2009 ; Location in patent: Page/Page column 157-158 ; WO 2009/011880 A2
  • Route3
    • In-stock
      5-Bromo-N1-methylbenzene-1,2-diamine|CS-W005679
      337915-79-4
    • null|null
      530-62-1
    • ~%
    • In-stock
      6-Bromo-1-methyl-1H-benzo[d]imidazol-2(3H)-one|CS-0058751
      305790-48-1

    References

    • MERCK SHARP and DOHME CORP.; DUDKIN, Vadim; FRALEY, Mark, E.; ARRINGTON, Kenneth, L.; LAYTON, Mark, E.; RODZINAK, Kevin, J.; PERO, Joseph, E.; REIF, Alexander, J. Patent: WO2012/21382 A1, 2012 ; Location in patent: Page/Page column 30 ; WO 2012/021382 A1

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   37.79
  • LogP   1.6291
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   0

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