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tert-Butyl but-3-en-1-ylcarbamate,98% (stabilized with MEHQ)

  • CAS No. 156731-40-7

  • Cat. No. CS-0033284
  • Purity95% (stabilized with MEHQ)
  • MDL No.MFCD11975862

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

tert-Butyl but-3-en-1-ylcarbamate,98% (stabilized with MEHQ)|CS-0033284

Structure of 156731-40-7

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General Information

  • CAS No. 156731-40-7
  • Cat. No. CS-0033284
  • Purity 95% (stabilized with MEHQ)
  • MDL No. MFCD11975862
  • Storage -20°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₁₇NO₂
  • Molecular Weight 171.24
  • Synonym(s) 1-(Boc-amino)-3-butene
  • SMILES O=C(OC(C)(C)C)NCCC=C

Description

tert-Butyl but-3-en-1-ylcarbamate, stabilized with MEHQ, is a bench-stable, moisture-tolerant building block featuring a terminal alkene and a protected amine. This combination enables efficient coupling reactions in synthetic workflows, where the vinyl group participates in cross-coupling or cycloaddition processes while the carbamate safeguards the amine functionality during transformation.

Application

tert-Butyl but-3-en-1-ylcarbamate serves as a versatile, bench-stable building block for late-stage functionalization and cross-coupling processes. Its pendant alkene enables efficient palladium-catalyzed transformations, while the tert-butyl carbamate group offers robust protection for primary amines with facile orthogonal deprotection. The stabilizer MEHQ prevents polymerization during storage and handling, ensuring consistent reactivity in synthetic workflows.

Synthesis

  • Route1
    • null|null
      2524-49-4
    • In-stock
      Di-tert-butyl dicarbonate|CS-0017817
      24424-99-5
    • ~59%
    • In-stock
      tert-Butyl but-3-en-1-ylcarbamate,98% (stabilized with MEHQ)|CS-0033284
      156731-40-7

    References

    • BRISTOL-MYERS SQUIBB COMPANY; BOY, Kenneth M.; GUERNON, Jason M.; MACOR, John E.; THOMPSON III, Lorin A.; WU, Yong-Jin; ZHANG, Yunhui Patent: WO2012/9309 A1, 2012 ; Location in patent: Page/Page column 56 ; WO 2012/009309 A1
  • Route2
    • null|null
      470443-12-0
    • ~93%
    • In-stock
      tert-Butyl but-3-en-1-ylcarbamate,98% (stabilized with MEHQ)|CS-0033284
      156731-40-7

    References

    • UNIVERSITY OF WOLLONGONG Patent: WO2006/74501 A1, 2006 ; Location in patent: Page/Page column 209 ;
  • Route3

    References

    • Pavlyuk, Oksana; Teller, Henrik; McMills, Mark C. Tetrahedron Letters, 2009 , vol. 50, # 23 p. 2716 - 2718

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07,GHS09
Signal Word : Warning
UN#: 3082
Class : 9
Packing Group : Ⅲ
Hazard Statements : H302-H410
Precautionary Statements : P264-P270-P273-P330-P391-P501

Quality Control

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Computational Chemistry Data

  • TPSA   38.33
  • LogP   2.0872
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   3

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