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CS-W001157 4
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Methyl 4-bromo-3-(trifluoromethyl)benzoate

  • CAS No. 107317-58-8

  • Cat. No. CS-W019106
  • Molecule weight283.04
  • Purity≥98%
  • MDL No.None

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

Methyl 4-bromo-3-(trifluoromethyl)benzoate|CS-W019106

Structure of 107317-58-8

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General Information

  • CAS No. 107317-58-8
  • Cat. No. CS-W019106
  • Purity ≥98%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₆BrF₃O₂
  • Molecular Weight 283.04
  • Synonym(s) None
  • SMILES O=C(OC)C1=CC=C(Br)C(C(F)(F)F)=C1

Description

Methyl 4-bromo-3-(trifluoromethyl)benzoate features a trifluoromethyl group positioned ortho to a bromine substituent on the aromatic ring, enhancing electron-withdrawing character and metabolic stability. This combination enables efficient cross-coupling reactions under palladium catalysis, delivering complex substituted arenes with high regiocontrol. The ester functionality supports further derivatization via hydrolysis or nucleophilic substitution.

Application

Methyl 4-bromo-3-(trifluoromethyl)benzoate serves as a versatile building block in medicinal chemistry and materials science, enabling palladium-catalyzed cross-coupling reactions due to its stable bromo and ester functionalities. The trifluoromethyl group enhances metabolic stability and lipophilicity, while the methyl ester allows for straightforward derivatization. Its bench-stable nature and compatibility with standard synthetic protocols facilitate efficient access to complex aromatic scaffolds.

Synthesis

  • Route1
    • null|null
      67-56-1
    • 2-Ethyl-2-(methoxymethyl)-[1,1-biphenyl]-4-carboxylic acid|CS-0931915
      1141473-97-3
    • ~91%
    • In-stock
      Methyl 4-bromo-3-(trifluoromethyl)benzoate|CS-W019106
      107317-58-8

    References

    • MERCK SERONO S.A.; QUATTROPANI, Anna; GERBER, Patrick; DORBAIS, Jerome Patent: WO2010/100142 A1, 2010 ; Location in patent: Page/Page column 54 ; WO 2010/100142 A1
  • Route2
    • null|null
      67-56-1
    • In-stock
      4-Bromo-3-(trifluoromethyl)benzoic acid|CS-W008399
      161622-14-6
    • ~97%
    • In-stock
      Methyl 4-bromo-3-(trifluoromethyl)benzoate|CS-W019106
      107317-58-8

    References

    • Huber, John D.; Bentzien, Joerg; Boyer, Stephen J.; Burke, Jennifer; De Lombaert, Stephane; Eickmeier, Christian; Guo, Xin; Haist, James V.; Hickey, Eugene R.; Kaplita, Paul; Karmazyn, Morris; Kemper, Raymond; Kennedy, Charles A.; Kirrane, Thomas; Madwed, Jeffrey B.; Mainolfi, Elizabeth; Nagaraja, Nelamangara; Soleymanzadeh, Fariba; Swinamer, Alan; Eldrup, Anne B. Journal of Medicinal Chemistry, 2012 , vol. 55, # 16 p. 7114 - 7140
  • Route3

    References

    • EP2017263 A1, ; Page/Page column 248-249 ; EP 2017263 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   3.2545
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   1

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