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(3-BROMO-BENZYL)-CARBAMIC ACID TERT-BUTYL ESTER

  • CAS No. 171663-13-1

  • Cat. No. CS-0036109
  • Purity≥98%
  • MDL No.None

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

(3-BROMO-BENZYL)-CARBAMIC ACID TERT-BUTYL ESTER|CS-0036109

Structure of 171663-13-1

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General Information

  • CAS No. 171663-13-1
  • Cat. No. CS-0036109
  • Purity ≥98%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₁₆BrNO₂
  • Molecular Weight 286.17
  • Synonym(s) Tert-butyl 3-bromobenzylcarbamate
  • SMILES CC(C)(C)OC(=NCC1=CC(=CC=C1)Br)O

Description

tert-Butyl (3-bromobenzyl)carbamate delivers a protected amine handle via a stable carbamate linkage, enabling straightforward deprotection under mild acidic conditions. The meta-bromophenyl moiety supports direct functionalization in cross-coupling reactions and provides a robust anchor for synthetic diversification in medicinal chemistry and materials development.

Application

tert-Butyl (3-bromobenzyl)carbamate serves as a versatile protecting group for primary amines, enabling selective functionalization in complex molecule synthesis. The ortho-bromo substituent provides a handle for subsequent cross-coupling reactions, while the tert-butyl carbamate moiety offers excellent bench stability and facile removal under mild acidic conditions. Its compatibility with palladium-catalyzed transformations and broad functional group tolerance make it a reliable building block for medicinal chemistry and API intermediate development.

Synthesis

  • Route1

    References

    • GALDERMA RESEARCH and DEVELOPMENT, S.N.C. Patent: WO2006/18325 A1, 2006 ; Location in patent: Page/Page column 28 - 29 ; WO 2006/018325 A1
  • Route2

    References

    • AXYS PHARMACEUTICALS, INC. Patent: WO2004/62661 A1, 2004 ; Location in patent: Page/Page column 24 ; WO 2004/062661 A1
  • Route3

    References

    • Eisai Co., Ltd. Patent: EP1380562 A1, 2004 ; Location in patent: Page 108 ;

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   41.82
  • LogP   3.6782
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   2

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