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tert-Butyl methyl(prop-2-yn-1-yl)carbamate

  • CAS No. 124045-51-8

  • Cat. No. CS-0142817
  • Purity≥95%
  • MDL No.MFCD22548360

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

tert-Butyl methyl(prop-2-yn-1-yl)carbamate|CS-0142817

Structure of 124045-51-8

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General Information

  • CAS No. 124045-51-8
  • Cat. No. CS-0142817
  • Purity ≥95%
  • MDL No. MFCD22548360
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₁₅NO₂
  • Molecular Weight 169.22
  • Synonym(s) tert-butyl N-methyl-N-prop-2-ynylcarbamate
  • SMILES O=C(OC(C)(C)C)N(C)CC#C

Description

tert-Butyl methyl(prop-2-yn-1-yl)carbamate features a propargylic carbamate moiety flanked by a tert-butyl group and a methyl-substituted alkyne, enabling selective protection of amines under mild conditions. This stable, bench-ready reagent integrates seamlessly into multistep syntheses, delivering efficient deprotection via acidolysis without affecting other functional groups.

Application

tert-Butyl methyl(prop-2-yn-1-yl)carbamate serves as a versatile, bench-stable carbamate protecting group for amines, enabling orthogonal protection in complex molecule synthesis. Its propargylic linkage facilitates selective deprotection under mild conditions and supports efficient coupling reactions via the alkyne handle. The compound exhibits excellent functional group tolerance and simplifies purification in multistep synthetic sequences, making it well-suited for peptide derivatization and heterocycle construction.

Synthesis

  • Route1
    • null|null
      35161-71-8
    • In-stock
      Di-tert-butyl dicarbonate|CS-0017817
      24424-99-5
    • ~97%
    • In-stock
      tert-Butyl methyl(prop-2-yn-1-yl)carbamate|CS-0142817
      124045-51-8

    References

    • Tetrahedron, , vol. 67, # 52 p. 10082 - 10088
  • Route2
    • In-stock
      Boc-Propargylamine|CS-M0556
      92136-39-5
    • null|null
      74-88-4
    • ~94%
    • In-stock
      tert-Butyl methyl(prop-2-yn-1-yl)carbamate|CS-0142817
      124045-51-8

    References

    • WO2013/169401 A1, ; Page/Page column 94 ;
  • Route3

    References

    • Tetrahedron, , vol. 65, # 31 p. 6156 - 6168

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H227-H315-H319-H335
Precautionary Statements : P210-P261-P264-P271-P280-P302+P352-P304+P340-P362+P364-P370+P378-P403-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   29.54
  • LogP   1.4865
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   1

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