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CS-W001157 4
Total: USD 88.00

2,2'-(Methylazanediyl)diacetic acid

  • CAS No. 4408-64-4

  • Cat. No. CS-W007872
  • Purity≥97%
  • MDL No.MFCD00004284

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

2,2'-(Methylazanediyl)diacetic acid|CS-W007872

Structure of 4408-64-4

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General Information

  • CAS No. 4408-64-4
  • Cat. No. CS-W007872
  • Purity ≥97%
  • MDL No. MFCD00004284
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₉NO₄
  • Molecular Weight 147.13
  • Synonym(s) None
  • SMILES CN(CC(O)=O)CC(O)=O

Description

N-Methyliminodiacetic acid features a methyl-substituted imino backbone that enhances solubility and metal-chelating efficiency. This derivative integrates readily into coordination complexes, offering improved stability in aqueous systems compared to unsubstituted analogs. The molecule’s polar carboxylate groups enable strong binding to transition metals, making it valuable for purification and catalytic applications.

Application

N-Methyliminodiacetic acid serves as a versatile bifunctional building block in synthetic chemistry, enabling efficient chelation and coordination in metal complexation. Its methylated iminodiacetic framework provides enhanced lipophilicity and metabolic stability compared to parent analogs, facilitating applications in radiolabeling agents and pharmaceutical intermediates. The molecule exhibits robust bench stability, tolerates diverse reaction conditions, and simplifies purification due to its polar yet crystalline nature—ideal for use in peptide conjugation, macrocyclic ligand synthesis, and the construction of targeted therapeutics.

Synthesis

  • Route1
    • null|null
      50-00-0
    • In-stock
      Iminodiacetic acid|CS-W013399
      142-73-4
    • ~86%
    • In-stock
      2,2'-(Methylazanediyl)diacetic acid|CS-W007872
      4408-64-4

    References

    • Ballmer, Steven G.; Gillis, Eric P.; Burke, Martin D.; Morton, Daniel; Davies, Huw M. L. Organic Syntheses, 2009 , vol. 86, p. 344 - 359
  • Route2
    • null|null
      1380504-17-5
    • ~%
    • In-stock
      2,2'-(Methylazanediyl)diacetic acid|CS-W007872
      4408-64-4
    • null|null
      1380504-25-5

    References

    • He, Zhi; Zajdlik, Adam; St. Denis, Jeffrey D.; Assem, Naila; Yudin, Andrei K. Journal of the American Chemical Society, 2012 , vol. 134, # 24 p. 9926 - 9929
  • Route3
    • In-stock
      Sarcosine|CS-W018511
      107-97-1
    • null|null
      79-11-8
    • ~49%
    • In-stock
      2,2'-(Methylazanediyl)diacetic acid|CS-W007872
      4408-64-4

    References

    • Kawashiro, Katsuhiro; Morimoto, Shiro; Yoshida, Hideyuki Bulletin of the Chemical Society of Japan, 1984 , vol. 57, # 4 p. 1097 - 1103

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H315-H319-H335
Precautionary Statements : P261-P264-P271-P280-P302+P352-P304+P340-P362-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   77.84
  • LogP   -0.9126
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   4

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