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6-Iodo-2(3H)-benzoxazolone

  • CAS No. 19932-87-7

  • Cat. No. CS-0308701
  • Purity≥97%
  • MDL No.MFCD08669499

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

6-Iodo-2(3H)-benzoxazolone|CS-0308701

Structure of 19932-87-7

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General Information

  • CAS No. 19932-87-7
  • Cat. No. CS-0308701
  • Purity ≥97%
  • MDL No. MFCD08669499
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₄INO₂
  • Molecular Weight 261.02
  • Synonym(s) 6-Iodo-2,3-dihydro-1,3-benzoxazol-2-one
  • SMILES O=C1OC2=CC(I)=CC=C2N1

Description

6-Iodo-2(3H)-benzoxazolone features a reactive iodine handle at the 6-position, enabling direct coupling in transition-metal-catalyzed transformations. The benzoxazolone core provides enhanced stability and facilitates incorporation into complex heterocyclic architectures under mild conditions. This compound serves as a robust scaffold for diversification in medicinal chemistry and materials synthesis.

Application

6-Iodo-2(3H)-benzoxazolone serves as a versatile building block in transition-metal-catalyzed cross-coupling reactions, enabling efficient access to functionalized benzoxazolone scaffolds. Its iodine substituent facilitates palladium-catalyzed coupling with arylboranes, alkenylstannanes, and other nucleophiles under standard conditions. The molecule exhibits good bench stability and reacts selectively at the C6 position, offering predictable regiochemistry for downstream synthesis of bioactive heterocycles and pharmaceutical intermediates.

Synthesis

  • Route1

    References

    • Gershon, Herman; Clarke, Donald D.; McMahon, John J.; Gershon, Muriel Monatshefte fur Chemie, 2002 , vol. 133, # 10 p. 1325 - 1330
  • Route2

    References

    • PTC THERAPEUTICS, INC.; HWANG, Peter Seongwoo; TAKASUGI, James; REN, Hongyu; WILDE, Richard Gerald; TURPOFF, Anthony; AREFOLOV, Alexander; KARP, Gary Mitchell; CHEN, Guangming; CAMPBELL, Jeffrey Allen Patent: WO2006/19831 A1, 2006 ; Location in patent: Page/Page column 445 ;

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

Quality Control

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Computational Chemistry Data

  • TPSA   46
  • LogP   1.7257
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   0

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