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CS-W001157 4
Total: USD 88.00

4-Methylbenzoic anhydride

  • CAS No. 13222-85-0

  • Cat. No. CS-W022217
  • Purity≥95%
  • MDL No.MFCD00048100

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

4-Methylbenzoic anhydride|CS-W022217

Structure of 13222-85-0

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General Information

  • CAS No. 13222-85-0
  • Cat. No. CS-W022217
  • Purity ≥95%
  • MDL No. MFCD00048100
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₆H₁₄O₃
  • Molecular Weight 254.28
  • Synonym(s) P-TOLUIC ANHYDRIDE
  • SMILES O=C(OC(C1=CC=C(C)C=C1)=O)C2=CC=C(C)C=C2

Description

4-Methylbenzoic anhydride delivers a reactive acylating moiety for efficient amide bond formation. The para-methyl group enhances electron density at the carbonyl, improving reactivity while maintaining bench-stable handling. This anhydride integrates readily into synthetic workflows requiring selective derivatization of amines and alcohols under mild conditions.

Application

4-Methylbenzoic anhydride serves as a versatile acylating agent in synthetic organic chemistry, enabling efficient ester and amide formation under mild conditions. Its benzylic methyl group enhances stability and facilitates purification, while the aromatic anhydride core exhibits high reactivity toward nucleophiles. This reagent functions reliably in standard bench-scale transformations, including peptide coupling and heterocycle functionalization, offering predictable yields and minimal side reactions.

Synthesis

  • Route1
    • null|null
      874-60-2
    • ~98%
    • In-stock
      4-Methylbenzoic anhydride|CS-W022217
      13222-85-0

    References

    • Hu, Yulai; Wang, Jin-Xian; Li, Shihua Synthetic Communications, 1997 , vol. 27, # 2 p. 243 - 248
  • Route2
    • null|null
      874-60-2
    • In-stock
      p-Toluic acid|CS-D0602
      99-94-5
    • ~93%
    • In-stock
      4-Methylbenzoic anhydride|CS-W022217
      13222-85-0

    References

    • Fife, Wilmer K.; Zhang, Zhi-dong Tetrahedron Letters, 1986 , vol. 27, # 41 p. 4933 - 4936
  • Route3
    • null|null
      201230-82-2
    • In-stock
      1-Iodo-4-methylbenzene|CS-W009210
      624-31-7
    • ~95%
    • In-stock
      4-Methylbenzoic anhydride|CS-W022217
      13222-85-0

    References

    • Li, Yang; Xue, Dong; Wang, Chao; Liu, Zhao-Tie; Xiao, Jianliang Chemical Communications, 2012 , vol. 48, # 9 p. 1320 - 1322

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

Quality Control

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Computational Chemistry Data

  • TPSA   43.37
  • LogP   3.30064
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   2

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