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CS-W001157 4
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(R)-3-(4-Bromo-3-fluorophenyl)-5-(hydroxymethyl)oxazolidin-2-one

  • CAS No. 444335-16-4

  • Cat. No. CS-M3231
  • Purity≥98%
  • MDL No.MFCD08166353

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

(R)-3-(4-Bromo-3-fluorophenyl)-5-(hydroxymethyl)oxazolidin-2-one|CS-M3231

Structure of 444335-16-4

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General Information

  • CAS No. 444335-16-4
  • Cat. No. CS-M3231
  • Purity ≥98%
  • MDL No. MFCD08166353
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₉BrFNO₃
  • Molecular Weight 290.09
  • Synonym(s) (5R)-3-(4-Bromo-3-fluorophenyl)-5-hydroxymethyloxazolidin-2-one
  • SMILES O=C1O[C@@H](CO)CN1C2=CC=C(Br)C(F)=C2

Description

(R)-3-(4-Bromo-3-fluorophenyl)-5-(hydroxymethyl)oxazolidin-2-one is a chiral oxazolidinone scaffold featuring a bromo-fluoroaryl substituent and a hydroxymethyl handle. This configuration enables direct incorporation into complex molecular architectures, particularly in asymmetric synthesis and medicinal chemistry applications. The molecule exhibits enhanced solubility and stability under standard conditions, facilitating efficient downstream functionalization.

Application

(R)-3-(4-Bromo-3-fluorophenyl)-5-(hydroxymethyl)oxazolidin-2-one serves as a versatile chiral building block for medicinal chemistry, enabling efficient access to bioactive heterocycles. Its well-defined stereochemistry and orthogonal functional groups—bromide for cross-coupling, fluorine for metabolic stability, and hydroxymethyl for further derivatization—facilitate modular synthesis of complex scaffolds. Bench-stable and compatible with standard reaction conditions, it supports scalable, high-yielding transformations in API development workflows.

Synthesis

  • Route1
    • Benzyl (4-bromo-3-fluorophenyl)carbamate|CS-0158605
      510729-01-8
    • (R)-Oxiran-2-ylmethyl butyrate Tedizolid  Impurity|CS-0229302
      60456-26-0
    • ~89%
    • In-stock
      (R)-3-(4-Bromo-3-fluorophenyl)-5-(hydroxymethyl)oxazolidin-2-one|CS-M3231
      444335-16-4

    References

    • LegoChem Biosciences, Inc.; CHO, Young Lag; BAEK, Sung Yoon; CHAE, Sang Eun; KIM, Sun Young; LEE, Hong Bum; LEE, Hyang Sook; OH, Kyuman; HEO, Hye Jin; PARK, Tae Kyo; WOO, Sung Ho; KIM, Yong Zu Patent: EP2692727 A2, 2014 ; Location in patent: Paragraph 0161-0162 ;
  • Route2

    References

    • GLOBAL ALLIANCE FOR TB DRUG DEVELOPMENT Patent: WO2009/120789 A1, 2009 ; Location in patent: Page/Page column 58 ;
  • Route3
    • In-stock
      (S)-3-Chloropropane-1,2-diol|CS-W011275
      60827-45-4
    • null|null
      288570-67-2
    • ~%
    • In-stock
      (R)-3-(4-Bromo-3-fluorophenyl)-5-(hydroxymethyl)oxazolidin-2-one|CS-M3231
      444335-16-4

    References

    • Gordeev, Mikhail F.; Patel, Dinesh V.; Barbachyn, Michael R.; Gage, James R. Patent: US2003/13737 A1, 2003 ;

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   49.77
  • LogP   1.9057
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   2

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