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CS-W001157 4
Total: USD 88.00

2-Amino-6-iodobenzoic acid

  • CAS No. 20776-52-7

  • Cat. No. CS-0041326
  • Molecule weight263.03
  • Purity≥98%
  • MDL No.MFCD07774160

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

2-Amino-6-iodobenzoic acid|CS-0041326

Structure of 20776-52-7

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General Information

  • CAS No. 20776-52-7
  • Cat. No. CS-0041326
  • Purity ≥98%
  • MDL No. MFCD07774160
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₆INO₂
  • Molecular Weight 263.03
  • Synonym(s) Benzoic acid, 2-amino-6-iodo-
  • SMILES O=C(O)C1=C(I)C=CC=C1N

Description

2-Amino-6-iodobenzoic acid features a carboxylic acid group flanked by an amino substituent and a bulky iodine atom at the para-position relative to the amine. This combination imparts strong electron-donating character and enhanced steric profile, enabling efficient coupling in palladium-catalyzed cross-coupling reactions. The molecule demonstrates excellent bench stability and solubility in polar organic solvents, facilitating straightforward integration into synthetic workflows for bioconjugation and pharmaceutical intermediate development.

Application

2-Amino-6-iodobenzoic acid serves as a versatile building block for constructing biologically relevant heterocycles and pharmaceutical intermediates. Its ortho-amino and iodine functionalities enable sequential cross-coupling and cyclization reactions, facilitating efficient access to complex scaffolds. The compound exhibits good bench stability and compatibility with standard purification methods, making it suitable for iterative synthesis workflows in medicinal chemistry and process development.

Synthesis

  • Route1
    • null|null
      5471-78-3
    • ~14%
    • In-stock
      2-Amino-6-iodobenzoic acid|CS-0041326
      20776-52-7
    • Methyl 2-amino-6-iodobenzoate|CS-0542397
      147494-20-0

    References

    • Seltzman, Herbert H.; Berrang, Bertold D. Tetrahedron Letters, 1993 , vol. 34, # 19 p. 3083 - 3086
  • Route2
    • 2-Iodo-6-nitrobenzoic acid|CS-1351781
      89641-04-3
    • ~59%
    • In-stock
      2-Amino-6-iodobenzoic acid|CS-0041326
      20776-52-7

    References

    • Kulhanek, Jiri; Pytela, Oldrich Collection of Czechoslovak Chemical Communications, 1997 , vol. 62, # 6 p. 913 - 924
  • Route3

    References

    • Snow,R.A. et al. Journal of the American Chemical Society, 1977 , vol. 99, p. 3734 - 3744

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-H312-H332
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-P363-P403+P233-P405-P501

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Computational Chemistry Data

  • TPSA   63.32
  • LogP   1.5716
  • H_Acceptors   2
  • H_Donors   2
  • Rotatable_Bonds   1

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