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CS-W001157 4
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tert-Butyl 3-(hydroxymethyl)benzylcarbamate

  • CAS No. 226070-69-5

  • Cat. No. CS-0041674
  • Purity≥97%
  • MDL No.MFCD06411554

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

tert-Butyl 3-(hydroxymethyl)benzylcarbamate|CS-0041674

Structure of 226070-69-5

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General Information

  • CAS No. 226070-69-5
  • Cat. No. CS-0041674
  • Purity ≥97%
  • MDL No. MFCD06411554
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₃H₁₉NO₃
  • Molecular Weight 237.29
  • Synonym(s) tert-butyl [3-(hydroxymethyl)benzyl]carbamate
  • SMILES CC(C)(C)OC(=O)NCC1=CC=CC(CO)=C1

Description

tert-Butyl 3-(hydroxymethyl)benzylcarbamate features a benzylcarbamate scaffold with a pendant hydroxymethyl group, enabling direct functionalization or derivatization. The tert-butyl carbamate moiety provides stable protection under standard conditions, while the benzylic alcohol offers a handle for oxidation or coupling reactions. This compound serves as a key intermediate in medicinal chemistry and peptide synthesis.

Application

tert-Butyl 3-(hydroxymethyl)benzylcarbamate serves as a versatile benzylamine-based building block for medicinal chemistry and process synthesis. The pendant hydroxymethyl group enables direct oxidation to aldehyde or carboxylic acid, while the tert-butyl carbamate (Boc) moiety provides stable protection of the amine under acidic conditions. This combination facilitates sequential functionalization and orthogonal deprotection workflows in complex molecule assembly.

Synthesis

  • Route1

    References

    • SUNESIS PHARMACEUTICALS; BIOGEN IDEC, INC. Patent: WO2008/5457 A2, 2008 ; Location in patent: Page/Page column 56 ; WO 2008/005457 A2
  • Route2

    References

    • Procopiou, Panayiotis A.; Barrett, John W.; Barton, Nicholas P.; Begg, Malcolm; Clapham, David; Copley, Royston C. B.; Ford, Alison J.; Graves, Rebecca H.; Hall, David A.; Hancock, Ashley P.; Hill, Alan P.; Hobbs, Heather; Hodgson, Simon T.; Jumeaux, Coline; Lacroix, Yannick M. L.; Miah, Afjal H.; Morriss, Karen M. L.; Needham, Deborah; Sheriff, Emma B.; Slack, Robert J.; Smith, Claire E.; Sollis, Steven L.; Staton, Hugo Journal of Medicinal Chemistry, 2013 , vol. 56, # 5 p. 1946 - 1960
  • Route3
    • null|null
      391957-11-2
    • In-stock
      Di-tert-butyl dicarbonate|CS-0017817
      24424-99-5
    • ~45%
    • In-stock
      tert-Butyl 3-(hydroxymethyl)benzylcarbamate|CS-0041674
      226070-69-5

    References

    • PHARMACIA CORPORATION Patent: WO2005/18557 A2, 2005 ; Location in patent: Page/Page column 282-283 ; WO 2005/018557 A2

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-H332-H335
Precautionary Statements : P260-P261-P264-P270-P271-P280-P301+P310-P302+P352-P304+P340-P304+P341-P305+P351+P338-P312-P330-P332+P313-P337+P313-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

  • TPSA   58.56
  • LogP   2.2036
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   3

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