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CS-W001157 4
Total: USD 88.00

4-(((tert-Butoxycarbonyl)amino)methyl)benzoic acid

  • CAS No. 33233-67-9

  • Cat. No. CS-W007869
  • Purity≥97%
  • MDL No.MFCD00228182

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

4-(((tert-Butoxycarbonyl)amino)methyl)benzoic acid|CS-W007869

Structure of 33233-67-9

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General Information

  • CAS No. 33233-67-9
  • Cat. No. CS-W007869
  • Purity ≥97%
  • MDL No. MFCD00228182
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₃H₁₇NO₄
  • Molecular Weight 251.28
  • Synonym(s) benzoic acid, 4-[[[(1,1-dimethylethoxy)carbonyl]amino]methyl]-
  • SMILES OC(C1=CC=C(CNC(OC(C)(C)C)=O)C=C1)=O

Description

This protected amino acid derivative features a tert-butoxycarbonyl group that stabilizes the amine functionality, enabling straightforward deprotection under mild acidic conditions. The para-substituted benzoic acid moiety provides a rigid aromatic handle for conjugation or incorporation into peptide-based systems, offering enhanced solubility and compatibility in synthetic workflows.

Application

4-(((tert-Butoxycarbonyl)amino)methyl)benzoic acid serves as a versatile building block for the synthesis of biologically relevant scaffolds, enabling efficient introduction of both carboxylic acid and protected amine functionalities. Its tert-butyl carbamate group offers excellent bench stability and compatibility with standard peptide coupling protocols, while the aromatic methylamine linker facilitates selective transformations. The molecule functions effectively in multi-step syntheses requiring orthogonal protection strategies.

Synthesis

  • Route1

    References

    • CHROMA THERAPEUTICS LTD. Patent: WO2008/40934 A1, 2008 ; Location in patent: Page/Page column 57-58 ; WO 2008/040934 A1
  • Route2

    References

    • CHROMA THERAPEUTICS LTD Patent: WO2006/117549 A1, 2006 ; Location in patent: Page/Page column 147 ; WO 2006/117549 A1
  • Route3
    • In-stock
      Di-tert-butyl dicarbonate|CS-0017817
      24424-99-5
    • 4-(Aminomethyl)benzoic acid hydrochloride|CS-0669874
      67688-72-6
    • ~53%
    • In-stock
      4-(((tert-Butoxycarbonyl)amino)methyl)benzoic acid|CS-W007869
      33233-67-9

    References

    • EVOTEC NEUROSCIENCES GMBH; MADDEN, James; HALLETT, David James; PARKES, Alastair; RAOOF, Ali; WANG, Xialou Patent: WO2010/20556 A1, 2010 ; Location in patent: Page/Page column 68 ; WO 2010/020556 A1

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   75.63
  • LogP   2.4095
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   3

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