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tert-Butyl (4-(hydroxymethyl)phenyl)carbamate

  • CAS No. 144072-29-7

  • Cat. No. CS-0032275
  • Purity≥98%
  • MDL No.MFCD04974271

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

tert-Butyl (4-(hydroxymethyl)phenyl)carbamate|CS-0032275

Structure of 144072-29-7

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General Information

  • CAS No. 144072-29-7
  • Cat. No. CS-0032275
  • Purity ≥98%
  • MDL No. MFCD04974271
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₁₇NO₃
  • Molecular Weight None
  • Synonym(s) tert-butyl N-[4-(hydroxyMethyl)phenyl]carbaMate
  • SMILES O=C(OC(C)(C)C)NC1=CC=C(CO)C=C1

Description

tert-Butyl (4-(hydroxymethyl)phenyl)carbamate features a benzyl alcohol handle appended to a tert-butyl carbamate-protected amine, enabling straightforward deprotection under mild acidic conditions. This stable, bench-ready reagent integrates readily into synthetic sequences requiring temporary nitrogen protection and offers compatibility with diverse functional groups.

Application

tert-Butyl (4-(hydroxymethyl)phenyl)carbamate serves as a stable, bench-friendly protecting group for primary amines, enabling selective functionalization of phenolic hydroxyls in para-substituted aryl systems. Its orthogonal stability allows for sequential transformations in complex molecule synthesis, with the carbamate cleavable under mild acidic conditions to reveal the free amine. Widely employed in medicinal chemistry and API development, it facilitates efficient access to functionalized aromatic scaffolds with high reproducibility and ease of purification.

Synthesis

  • Route1

    References

    • ENZON PHARMACEUTICALS, INC. Patent: WO2008/34124 A2, 2008 ; Location in patent: Page/Page column 72-73 ;
  • Route2

    References

    • EP2123637 A1, ; Page/Page column 75 ;
  • Route3
    • In-stock
      Di-tert-butyl dicarbonate|CS-0017817
      24424-99-5
    • 4-Aminobenzoic acid Conivaptan Impurity|CS-0213989
      150-13-0
    • ~10%
    • In-stock
      tert-Butyl (4-(hydroxymethyl)phenyl)carbamate|CS-0032275
      144072-29-7

    References

    • Byun, Ji Hun; Kim, HyeYun; Kim, YoungSoo; Mook-Jung, Inhee; Kim, Dong Jin; Lee, Won Koo; Yoo, Kyung Ho Bioorganic and Medicinal Chemistry Letters, 2008 , vol. 18, # 20 p. 5591 - 5593

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H315-H319-H335
Precautionary Statements : P260-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

  • TPSA   58.56
  • LogP   2.5259
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   2

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