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CS-W001157 4
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tert-Butyl (6-iodohexyl)carbamate

  • CAS No. 172846-36-5

  • Cat. No. CS-0375733
  • Purity≥97%
  • MDL No.MFCD09951827

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

tert-Butyl (6-iodohexyl)carbamate|CS-0375733

Structure of 172846-36-5

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General Information

  • CAS No. 172846-36-5
  • Cat. No. CS-0375733
  • Purity ≥97%
  • MDL No. MFCD09951827
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₂₂INO₂
  • Molecular Weight 327.20
  • Synonym(s) None
  • SMILES O=C(OC(C)(C)C)NCCCCCCI

Description

tert-Butyl (6-iodohexyl)carbamate is a bench-stable, moisture-tolerant carbamate protecting group that integrates a reactive iodide handle at the distal end of a six-carbon chain. This structure enables efficient coupling in late-stage functionalization and diversification workflows. The pendant iodine atom facilitates transition metal-catalyzed transformations such as cross-couplings, enabling rapid access to complex molecular architectures.

Application

tert-Butyl (6-iodohexyl)carbamate serves as a versatile bifunctional building block for C–C and C–heteroatom coupling reactions. The iodide moiety enables reliable Stille, Suzuki, and Negishi cross-couplings, while the tert-butoxycarbonyl (Boc) group provides orthogonal protection for primary amines. Its bench-stable nature and ease of purification facilitate integration into multi-step syntheses, including peptidomimetics and functionalized alkyl chains in medicinal chemistry.

Synthesis

  • Route1

    References

    • Dutton, Jonathan K.; Knox, John H.; Radisson, Xavier; Ritchie, Harold J.; Ramage, Robert Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1995 , # 20 p. 2581 - 2588
  • Route2
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    • In-stock
      tert-Butyl (6-iodohexyl)carbamate|CS-0375733
      172846-36-5

    References

    • Isomura; Wirsching; Janda Journal of Organic Chemistry, 2001 , vol. 66, # 12 p. 4115 - 4121
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    References

    • Culcasi, Marcel; Casano, Gilles; Lucchesi, Celine; Mercier, Anne; Clement, Jean-Louis; Pique, Valerie; Michelet, Laure; Krieger-Liszkay, Anja; Robin, Maxime; Pietri, Sylvia Journal of Medicinal Chemistry, 2013 , vol. 56, # 6 p. 2487 - 2499

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-P330-P362+P364-P405-P501

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Computational Chemistry Data

  • TPSA   38.33
  • LogP   3.5065
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   6

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