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CS-W001157 4
Total: USD 88.00

4-Benzyloxy-3,3-dimethylbut-1-yne

  • CAS No. 1092536-54-3

  • Cat. No. CS-M2008
  • Molecule weight188.27
  • Purity≥98%
  • MDL No.MFCD23106327

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

4-Benzyloxy-3,3-dimethylbut-1-yne|CS-M2008

Structure of 1092536-54-3

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General Information

  • CAS No. 1092536-54-3
  • Cat. No. CS-M2008
  • Purity ≥98%
  • MDL No. MFCD23106327
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₃H₁₆O
  • Molecular Weight 188.27
  • Synonym(s) 2,2-dimethylbut-3-ynoxymethylbenzene
  • SMILES CC(COCC1=CC=CC=C1)(C)C#C

Description

4-Benzyloxy-3,3-dimethylbut-1-yne features a benzyl ether-functionalized alkyne with steric protection from the dimethyl-substituted terminus. This bench-stable building block enables direct incorporation into copper-catalyzed azide-alkyne cycloaddition (CuAAC) reactions, offering reliable conjugation in bioorthogonal labeling and polymer synthesis workflows.

Application

4-Benzyloxy-3,3-dimethylbut-1-yne serves as a versatile building block for the synthesis of functionalized alkynes and heterocyclic scaffolds. Its terminal alkyne functionality enables efficient copper-catalyzed coupling reactions, while the benzyloxy group offers orthogonal protection and enhanced solubility. The sterically hindered dimethyl-substituted chain improves stability and simplifies purification, making it well-suited for iterative synthetic sequences in medicinal chemistry and materials science applications.

Synthesis

  • Route1
    • (4-(Benzyloxy)-3,3-dimethylbut-1-yn-1-yl)trimethylsilane|CS-M2011
      1294504-65-6
    • ~%
    • In-stock
      4-Benzyloxy-3,3-dimethylbut-1-yne|CS-M2008
      1092536-54-3

    References

    • VERTEX PHARMACEUTICALS INCORPORATED; KESHAVARZ-SHOKRI, Ali; ZHANG, Beili; ALCACIO, Tim, Edward; LEE, Elaine, Chungmin; ZHANG, Yuegang; KRAWIEC, Mariusz Patent: WO2011/119984 A1, 2011 ; Location in patent: Page/Page column 54 ; WO 2011/119984 A1
  • Route2
    • null|null
      1402615-92-2
    • ~96%
    • In-stock
      4-Benzyloxy-3,3-dimethylbut-1-yne|CS-M2008
      1092536-54-3

    References

    • Ozawa, Tsukasa; Kanematsu, Makoto; Yokoe, Hiromasa; Yoshida, Masahiro; Shishido, Kozo Journal of Organic Chemistry, 2012 , vol. 77, # 20 p. 9240 - 9249,10 Title/Abstract Full Text Show Details Ozawa, Tsukasa; Kanematsu, Makoto; Yokoe, Hiromasa; Yoshida, Masahiro; Shishido, Kozo Journal of Organic Chemistry, 2012 , vol. 77, # 20 p. 9240 - 9249
  • Route3
    • null|null
      38216-93-2
    • null|null
      60190-80-9
    • ~79%
    • In-stock
      4-Benzyloxy-3,3-dimethylbut-1-yne|CS-M2008
      1092536-54-3

    References

    • Taber, Douglass F.; Bai, Sha; Guo, Peng-fei Tetrahedron Letters, 2008 , vol. 49, # 48 p. 6904 - 6906

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
Precautionary Statements : P264-P270-P330-P501

Quality Control

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Computational Chemistry Data

  • TPSA   9.23
  • LogP   2.8626
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   4

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