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CS-W001157 4
Total: USD 88.00

Methyl 2-(4-bromophenyl)-2,2-dimethylacetate

  • CAS No. 154825-97-5

  • Cat. No. CS-W018999
  • Purity≥98%
  • MDL No.MFCD02683357

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

Methyl 2-(4-bromophenyl)-2,2-dimethylacetate|CS-W018999

Structure of 154825-97-5

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General Information

  • CAS No. 154825-97-5
  • Cat. No. CS-W018999
  • Purity ≥98%
  • MDL No. MFCD02683357
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₁₃BrO₂
  • Molecular Weight 257.12
  • Synonym(s) P-Bromo-Alpha,Alpha-Dimethyl Phenylacetic
  • SMILES BrC1=CC=C(C=C1)C(C(=O)OC)(C)C

Description

Methyl 2-(4-bromophenyl)-2,2-dimethylacetate is a bench-stable, moisture-tolerant building block featuring a sterically hindered quaternary carbon center. The para-bromophenyl group imparts enhanced reactivity in palladium-catalyzed cross-coupling processes, while the ester functionality enables straightforward derivatization. This compound integrates efficiently into complex molecular architectures requiring robust aryl-alkyl linkages.

Application

Methyl 2-(4-bromophenyl)-2,2-dimethylacetate serves as a versatile building block for Suzuki-Miyaura coupling reactions, enabling efficient construction of biaryl scaffolds. The bromophenyl group exhibits high reactivity under standard palladium catalysis, while the sterically hindered gem-dimethylacetyl moiety provides excellent bench stability and facilitates straightforward purification. Its compatibility with diverse reaction conditions makes it a reliable intermediate in the synthesis of functionalized aromatic compounds and pharmaceutical precursors.

Synthesis

  • Route1
    • In-stock
      Methyl 4-bromophenylacetate|CS-M1488
      41841-16-1
    • null|null
      74-88-4
    • ~95%
    • In-stock
      Methyl 2-(4-bromophenyl)-2,2-dimethylacetate|CS-W018999
      154825-97-5

    References

    • JONES, Philip; DIFRANCESCO, Maria, Emilia; PETROCCHI, Alessia; MARSZALEK, Joe; LIU, Gang; KANG, Zhijun; CARROLL, Christopher, L.; MCAFOOS, Timothy; CZAKO, Barbara Patent: WO2014/31928 A2, 2014 ; Location in patent: Paragraph 0398 ;
  • Route2
    • null|null
      67-56-1
    • In-stock
      2-(4-Bromophenyl)-2-methylpropanoic acid|CS-M1477
      32454-35-6
    • ~97%
    • In-stock
      Methyl 2-(4-bromophenyl)-2,2-dimethylacetate|CS-W018999
      154825-97-5

    References

    • Dawar, Pankaj; Raju, M. Bagavan; Ramakrishna, Ramesha Andagar Synthetic Communications, 2014 , vol. 44, # 6 p. 836 - 846
  • Route3
    • In-stock
      Methyl 2-(4-bromophenyl)propanoate|CS-0096048
      83636-46-8
    • null|null
      74-88-4
    • ~%
    • In-stock
      Methyl 2-(4-bromophenyl)-2,2-dimethylacetate|CS-W018999
      154825-97-5

    References

    • WO2005/19161 A1, ; Page/Page column 65 ; WO 2005/019161 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   26.3
  • LogP   2.8997
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   2

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