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CS-W001157 4
Total: USD 88.00

tert-Butyl 2-hydroxy-2-methylpropylcarbamate

  • CAS No. 183059-24-7

  • Cat. No. CS-W019142
  • Molecule weight189.25
  • Purity≥98%
  • MDL No.None

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

tert-Butyl 2-hydroxy-2-methylpropylcarbamate|CS-W019142

Structure of 183059-24-7

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General Information

  • CAS No. 183059-24-7
  • Cat. No. CS-W019142
  • Purity ≥98%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₁₉NO₃
  • Molecular Weight 189.25
  • Synonym(s) tert-butyl N-(2-hydroxy-2-methylpropyl)carbamate
  • SMILES O=C(OC(C)(C)C)NCC(C)(O)C

Description

tert-Butyl 2-hydroxy-2-methylpropylcarbamate features a sterically hindered carbamate group that enhances stability under standard conditions. This bench-stable derivative enables reliable protection of amine functionalities during synthetic manipulations, particularly in peptide coupling and modular synthesis workflows.

Application

tert-Butyl 2-hydroxy-2-methylpropylcarbamate serves as a stable, bench-friendly amino protecting group precursor, enabling selective N-alkylation and subsequent deprotection under mild acidic conditions. Its tertiary butyl carbamate moiety offers excellent functional group tolerance and facilitates purification via standard chromatographic methods. The pendant hydroxyl group allows for orthogonal derivatization in complex molecule synthesis, making it a practical choice for peptide analogs and heterocyclic scaffolds requiring controlled reactivity and stability during multi-step sequences.

Synthesis

  • Route1
    • In-stock
      Boc-Gly-OMe|CS-W022602
      31954-27-5
    • null|null
      75-16-1
    • ~67%
    • In-stock
      tert-Butyl 2-hydroxy-2-methylpropylcarbamate|CS-W019142
      183059-24-7

    References

    • Jones, Simon; Smanmoo, Chaiwat Tetrahedron Letters, 2004 , vol. 45, # 8 p. 1585 - 1588
  • Route2

    References

    • Novo Nordisk A/S Patent: US5977178 A1, 1999 ;
  • Route3

    References

    • Shukla, Nikunj M.; Kimbrell, Matthew R.; Malladi, Subbalakshmi S.; David, Sunil A. Bioorganic and Medicinal Chemistry Letters, 2009 , vol. 19, # 8 p. 2211 - 2214

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

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Computational Chemistry Data

  • TPSA   58.56
  • LogP   1.282
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   2

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