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CS-W001157 4
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2-Iodo-5-nitrobenzoic acid

  • CAS No. 19230-50-3

  • Cat. No. CS-0041122
  • Purity≥97%
  • MDL No.MFCD00234256

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

2-Iodo-5-nitrobenzoic acid|CS-0041122

Structure of 19230-50-3

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General Information

  • CAS No. 19230-50-3
  • Cat. No. CS-0041122
  • Purity ≥97%
  • MDL No. MFCD00234256
  • Storage RT, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₄INO₄
  • Molecular Weight 293.02
  • Synonym(s) benzoic acid, 2-iodo-5-nitro-
  • SMILES O=C(O)C1=CC([N+]([O-])=O)=CC=C1I

Description

2-Iodo-5-nitrobenzoic acid features a carboxylic acid group flanked by iodine and nitro substituents at adjacent positions on the benzene ring. This electron-deficient aryl iodide enables direct coupling in transition-metal-catalyzed reactions, while the ortho-iodo and para-nitro groups enhance reactivity and stability under standard conditions.

Application

2-Iodo-5-nitrobenzoic acid serves as a versatile building block in transition-metal-catalyzed cross-coupling reactions, enabling efficient construction of biaryl and functionalized heterocyclic scaffolds. The iodide group facilitates reliable Suzuki, Stille, and Negishi couplings, while the nitro and carboxylic acid functionalities provide orthogonal handles for further derivatization. Its bench-stable crystalline form simplifies handling and purification, making it well-suited for iterative synthesis in medicinal chemistry and materials development.

Synthesis

  • Route1

    References

    • Cui, Li-Qian; Dong, Zhi-Lei; Liu, Kai; Zhang, Chi Organic Letters, 2011 , vol. 13, # 24 p. 6488 - 6491
  • Route2

    References

    • Iinuma, Masataka; Moriyama, Katsuhiko; Togo, Hideo Synlett, 2013 , vol. 24, # 13 art. no. ST-2013-U0386-L, p. 1707 - 1711
  • Route3

    References

    • Barbasiewicz, Michal; Blocki, Krzysztof; Malinska, Maura; Pawlowski, Robert Dalton Transactions, 2013 , vol. 42, # 2 p. 355 - 358

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-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

  • TPSA   80.44
  • LogP   1.8976
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   2

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