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CS-W001157 4
Total: USD 88.00

Benzyl (4-nitrophenyl) carbonate

  • CAS No. 13795-24-9

  • Cat. No. CS-0156216
  • Purity≥97%
  • MDL No.MFCD00007323

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

Benzyl (4-nitrophenyl) carbonate|CS-0156216

Structure of 13795-24-9

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General Information

  • CAS No. 13795-24-9
  • Cat. No. CS-0156216
  • Purity ≥97%
  • MDL No. MFCD00007323
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₄H₁₁NO₅
  • Molecular Weight 273.24
  • Synonym(s) Carbonic acid, 4-nitrophenyl phenylmethyl ester
  • SMILES C1=CC=C(C=C1)COC(=O)OC2=CC=C(C=C2)[N+](=O)[O-]

Description

Benzyl (4-nitrophenyl) carbonate serves as a stable, bench-ready protecting group for alcohols and thiols, enabling selective deprotection under mild conditions. The electron-deficient para-nitro group enhances leaving group ability, while the benzyl moiety offers orthogonal cleavage options. This reagent integrates seamlessly into synthetic workflows requiring precise functional group management.

Application

Benzyl (4-nitrophenyl) carbonate serves as a stable, bench-ready carbonylating agent for hydroxyl and amine functional groups. It facilitates efficient O- and N-carbamylation under mild conditions, enabling rapid access to protected intermediates in peptide synthesis and medicinal chemistry workflows. The 4-nitrophenyl leaving group ensures high reactivity with nucleophiles while maintaining excellent shelf stability and ease of purification.

Synthesis

  • Route1
    • null|null
      100-02-7
    • null|null
      501-53-1
    • ~97%
    • In-stock
      Benzyl (4-nitrophenyl) carbonate|CS-0156216
      13795-24-9

    References

    • Tepe, Jetze J.; Madalengoitia, Jose S.; Slunt, Kelli M.; Werbovetz, Karl W.; Spoors, P. Grant; Macdonald, Timothy L. Journal of Medicinal Chemistry, 1996 , vol. 39, # 11 p. 2188 - 2196
  • Route2

    References

    • Chemische Berichte, , vol. 99, p. 3914 - 3924
  • Route3
    • null|null
      100-02-7
    • null|null
      1885-14-9
    • ~82%
    • In-stock
      Benzyl (4-nitrophenyl) carbonate|CS-0156216
      13795-24-9

    References

    • Boykin, David W.; Rahmathullah, M. Syed; Tidwell, Richard R.; Hall, James E. Patent: US2002/19437 A1, 2002 ;

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   78.67
  • LogP   3.3104
  • H_Acceptors   5
  • H_Donors   0
  • Rotatable_Bonds   4

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