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CS-W001157 4
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3-Iodo-4-methylbenzoic acid

  • CAS No. 82998-57-0

  • Cat. No. CS-W020661
  • Purity≥98%
  • MDL No.MFCD00010392

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

3-Iodo-4-methylbenzoic acid|CS-W020661

Structure of 82998-57-0

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General Information

  • CAS No. 82998-57-0
  • Cat. No. CS-W020661
  • Purity ≥98%
  • MDL No. MFCD00010392
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₇IO₂
  • Molecular Weight 262.04
  • Synonym(s) 3-Iodo-4-methylbenzoic acid; 3-Iodo-4-Nitrobenzoic acid
  • SMILES O=C(O)C1=CC=C(C)C(I)=C1

Description

3-Iodo-4-methylbenzoic acid features a para-substituted aromatic core with iodine and methyl groups flanking a carboxylic acid moiety. This configuration enables direct functionalization in cross-coupling reactions, while the electron-deficient aryl halide facilitates palladium-catalyzed transformations. The molecule exhibits robust stability under standard handling conditions and integrates readily into complex molecular architectures requiring precise substitution patterns.

Application

3-Iodo-4-methylbenzoic acid serves as a versatile building block for Suzuki-Miyaura and Stille couplings, enabling efficient access to biaryl and heteroaryl scaffolds. The iodine handle provides high reactivity under standard palladium catalysis, while the carboxylic acid facilitates direct derivatization or salt formation. Its bench-stable crystalline form simplifies handling and purification, making it well-suited for medicinal chemistry and process development workflows.

Synthesis

  • Route1

    References

    • BRISTOL-MYERS SQUIBB COMPANY; PRACITTO, Richard; KADOW, John, F.; BENDER, John, A.; BENO, Brett, R.; GRANT-YOUNG, Katharine; HAN, Ying; HEWAWASAM, Piyasena; NICKEL, Andrew; PARCELLA, Kyle, E.; YEUNG, Kap-Sun; CHUPAK, Louis, S. Patent: WO2011/112186 A1, 2011 ; Location in patent: Page/Page column 196 ; WO 2011/112186 A1
  • Route2

    References

    • Azarifar, Davood; Khosravi, Kaveh; Najminejad, Zohreh; Soleimani, Khadijeh Journal of the Iranian Chemical Society, 2012 , vol. 9, # 3 p. 321 - 326
  • Route3

    References

    • Journal of the Chemical Society, , vol. 103, p. 236

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   37.3
  • LogP   2.29782
  • H_Acceptors   1
  • H_Donors   1
  • Rotatable_Bonds   1

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