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tert-Butyl (1-(bromomethyl)cyclopropyl)carbamate

  • CAS No. 387845-49-0

  • Cat. No. CS-0088314
  • Purity≥97%
  • MDL No.MFCD23701521

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

tert-Butyl (1-(bromomethyl)cyclopropyl)carbamate|CS-0088314

Structure of 387845-49-0

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General Information

  • CAS No. 387845-49-0
  • Cat. No. CS-0088314
  • Purity ≥97%
  • MDL No. MFCD23701521
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₁₆BrNO₂
  • Molecular Weight 250.13
  • Synonym(s) Tert-butyl n-[1-(bromomethyl)cyclopropyl]carbamate
  • SMILES BrCC1(NC(OC(C)(C)C)=O)CC1

Description

tert-Butyl (1-(bromomethyl)cyclopropyl)carbamate delivers a cyclopropyl ring tethered to a bromomethyl group, enabling direct functionalization at the strained ring junction. The tert-butyl carbamate moiety provides stability and ease of removal under mild acidic conditions. This reagent facilitates efficient incorporation of cyclopropyl motifs into complex molecular architectures.

Application

tert-Butyl (1-(bromomethyl)cyclopropyl)carbamate serves as a versatile building block for cyclopropyl-containing scaffolds in medicinal chemistry. The bromomethyl group enables efficient nucleophilic substitution, facilitating C–C and C–heteroatom bond formation under mild conditions. Its tert-butyl carbamate protection offers excellent bench stability and compatibility with diverse reaction environments, simplifying purification and enabling sequential functionalization. This reagent is particularly valuable for constructing bioactive cyclopropyl motifs in API development.

Synthesis

  • Route1

    References

    • Charton, Yves; Guillonneau, Claude; Lockhart, Brian; Lestage, Pierre; Goldstein, Solo Bioorganic and Medicinal Chemistry Letters, 2008 , vol. 18, # 6 p. 2188 - 2193

Safety Information

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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   38.33
  • LogP   2.4386
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   2

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