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CS-W001157 4
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(E)-2-(3-Chloroprop-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

  • CAS No. 153724-93-7

  • Cat. No. CS-0175025
  • Purity≥95%
  • MDL No.MFCD09260446

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

(E)-2-(3-Chloroprop-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-0175025

Structure of 153724-93-7

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General Information

  • CAS No. 153724-93-7
  • Cat. No. CS-0175025
  • Purity ≥95%
  • MDL No. MFCD09260446
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₁₆BClO₂
  • Molecular Weight 202.49
  • Synonym(s) 3-Chloropropenyl-1-boronic acid pinacol ester,2-(3-Chloro-propenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane
  • SMILES CC1(C(C)(OB(O1)/C=C/CCl)C)C

Application

(E)-2-(3-Chloroprop-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane serves as a stable, bench-ready boron building block for palladium-catalyzed cross-coupling reactions. Its (E)-configured vinyl boronate enables stereoselective incorporation into conjugated systems, while the tetramethyl-substituted dioxaborolane enhances stability and functional group tolerance. The molecule facilitates efficient coupling with aryl, heteroaryl, and vinyl halides, offering reliable access to functionalized alkenes in synthetic and medicinal chemistry workflows.

Synthesis

  • Route1
    • In-stock
      2,3-Dimethylbutane-2,3-diol|CS-0015356
      76-09-5
    • (E)-(3-Chloroprop-1-en-1-yl)boronic acid|CS-1639085
      491879-29-9
    • ~98%
    • In-stock
      (E)-2-(3-Chloroprop-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-0175025
      153724-93-7

    References

    • Ban, Hyun Seung; Usui, Taikou; Nabeyama, Wataru; Morita, Hidetoshi; Fukuzawa, Kaori; Nakamura, Hiroyuki Organic and Biomolecular Chemistry, 2009 , vol. 7, # 21 p. 4415 - 4427
  • Route2
    • In-stock
      2,3-Dimethylbutane-2,3-diol|CS-0015356
      76-09-5
    • null|null
      37490-26-9
    • ~%
    • In-stock
      (E)-2-(3-Chloroprop-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-0175025
      153724-93-7

    References

    • Synthesis, , # 11 p. 1814 - 1820
  • Route3
    • In-stock
      2,3-Dimethylbutane-2,3-diol|CS-0015356
      76-09-5
    • null|null
      624-65-7
    • ~%
    • In-stock
      (E)-2-(3-Chloroprop-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-0175025
      153724-93-7

    References

    • European Journal of Organic Chemistry, , # 16 p. 2823 - 2830

Safety Information

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Precautionary Statements : N/A

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Computational Chemistry Data

  • TPSA   18.46
  • LogP   2.4128
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   2

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