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CS-W001157 4
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(2-Bromo-5-(trifluoromethyl)phenyl)methanol

  • CAS No. 869725-53-1

  • Cat. No. CS-W019561
  • Purity≥97%
  • MDL No.MFCD04973761

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

(2-Bromo-5-(trifluoromethyl)phenyl)methanol|CS-W019561

Structure of 869725-53-1

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General Information

  • CAS No. 869725-53-1
  • Cat. No. CS-W019561
  • Purity ≥97%
  • MDL No. MFCD04973761
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₆BrF₃O
  • Molecular Weight 255.03
  • Synonym(s) 2-Bromo-5-Trilfuoromethylbenzyl Alcohol
  • SMILES OCC1=CC(C(F)(F)F)=CC=C1Br

Description

This boronate moiety integrates a trifluoromethyl group and a bromo substituent on a phenyl ring, delivering enhanced electron-withdrawing character and improved stability under standard conditions. The methanol functionality enables direct coupling or oxidation to carboxylic acid derivatives in synthetic sequences.

Application

(2-Bromo-5-(trifluoromethyl)phenyl)methanol serves as a versatile building block in medicinal chemistry, enabling palladium-catalyzed cross-coupling reactions due to its stable bromo and benzyl alcohol functionalities. The trifluoromethyl group imparts enhanced metabolic stability and lipophilicity, while the benzylic alcohol allows for derivatization via oxidation or protection. Its bench-stable nature and compatibility with standard reaction conditions facilitate efficient synthesis of complex arylated scaffolds.

Synthesis

  • Route1

    References

    • Xue, Chu-Biao; Chen, Lihua; Cao, Ganfeng; Zhang, Ke; Wang, Anlai; Meloni, David; Glenn, Joseph; Anand, Rajan; Xia, Michael; Kong, Ling; Huang, Taisheng; Feng, Hao; Zheng, Changsheng; Li, Mei; Galya, Laurine; Zhou, Jiacheng; Shin, Niu; Baribaud, Fredric; Solomon, Kim; Scherle, Peggy; Zhao, Bitao; Diamond, Sharon; Emm, Tom; Keller, Douglas; Contel, Nancy; Yeleswaram, Swamy; Vaddi, Kris; Hollis, Gregory; Newton, Robert; Friedman, Steven; Metcalf, Brian ACS Medicinal Chemistry Letters, 2010 , vol. 1, # 9 p. 483 - 487
  • Route2

    References

    • WO2006/56854 A1, ; Page/Page column 56 ;
  • Route3
    • null|null
      50-00-0
    • In-stock
      1-Bromo-2-iodo-4-(trifluoromethyl)benzene|CS-W013907
      640280-28-0
    • ~60%
    • In-stock
      (2-Bromo-5-(trifluoromethyl)phenyl)methanol|CS-W019561
      869725-53-1

    References

    • Severin, Rene; Mujahidin, Didin; Reimer, Jessica; Doye, Sven Heterocycles, 2007 , vol. 74, # C p. 683 - 700

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   20.23
  • LogP   2.9602
  • H_Acceptors   1
  • H_Donors   1
  • Rotatable_Bonds   1

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