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CS-W001157 4
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Benzyl N-[1-(hydroxymethyl)cyclopropyl]carbamate

  • CAS No. 103500-22-7

  • Cat. No. CS-M2548
  • Molecule weight221.25
  • Purity≥97%
  • MDL No.MFCD16294221

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

Benzyl N-[1-(hydroxymethyl)cyclopropyl]carbamate|CS-M2548

Structure of 103500-22-7

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General Information

  • CAS No. 103500-22-7
  • Cat. No. CS-M2548
  • Purity ≥97%
  • MDL No. MFCD16294221
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₁₅NO₃
  • Molecular Weight 221.25
  • Synonym(s) N-[1-(Hydroxymethyl)Cyclopropyl]Carbamic Acid Phenylmethyl Ester
  • SMILES O=C(OCC1=CC=CC=C1)NC2(CO)CC2

Description

Benzyl N-[1-(hydroxymethyl)cyclopropyl]carbamate features a cyclopropyl ring bearing a hydroxymethyl group and a carbamate linkage, enabling its use in peptide synthesis and medicinal chemistry. The benzylic carbamate serves as a stable, removable protecting group for amines under standard conditions. This compound delivers precise functionalization in complex molecule assembly.

Application

Benzyl N-[1-(hydroxymethyl)cyclopropyl]carbamate serves as a versatile chiral building block in medicinal chemistry, enabling the synthesis of cyclopropyl-containing scaffolds via selective deprotection and functionalization. The benzyl carbamate group offers excellent bench stability and orthogonal cleavage under mild hydrogenolysis conditions, while the hydroxymethyl functionality permits further derivatization through oxidation or protection. Its compatibility with standard coupling reactions and ease of purification make it a practical choice for API intermediate development.

Synthesis

  • Route1

    References

    • WO2008/64157 A1, ; Page/Page column 103 ;
  • Route2
    • Ethyl 1-(((benzyloxy)carbonyl)amino)cyclopropanecarboxylate|CS-0699111
      85452-41-1
    • ~89%
    • In-stock
      Benzyl N-[1-(hydroxymethyl)cyclopropyl]carbamate|CS-M2548
      103500-22-7

    References

    • Journal of Medicinal Chemistry, , vol. 29, # 10 p. 1840 - 1846
  • Route3
    • Ethyl 1-(((benzyloxy)carbonyl)amino)cyclopropanecarboxylate|CS-0699111
      85452-41-1
    • ~44%
    • null|null
      103500-23-8
    • In-stock
      Benzyl N-[1-(hydroxymethyl)cyclopropyl]carbamate|CS-M2548
      103500-22-7

    References

    • Journal of Medicinal Chemistry, , vol. 29, # 10 p. 1840 - 1846

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   1.4377
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   4

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