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56781

Sigma-Aldrich

Iminodiacetic acid

≥98.0% (T), for peptide synthesis

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Synonym(s):
IDA
Linear Formula:
HN(CH2COOH)2
CAS Number:
Molecular Weight:
133.10
Beilstein/REAXYS Number:
878499
EC Number:
MDL number:
UNSPSC Code:
12352106
PubChem Substance ID:
NACRES:
NA.22

grade

purum

Quality Level

assay

≥98.0% (T)

form

solid

mp

243 °C (dec.) (lit.)

application(s)

peptide synthesis

SMILES string

OC(=O)CNCC(O)=O

InChI

1S/C4H7NO4/c6-3(7)1-5-2-4(8)9/h5H,1-2H2,(H,6,7)(H,8,9)

InChI key

NBZBKCUXIYYUSX-UHFFFAOYSA-N

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Application

Iminodiacetic acid (IDA) can be used as a tridentate ligand to chelate metal ions. Some of the common applications of IDA include:
  • Synthesis of N-methyliminodiacetic acid (MIDA), which is an essential precursor for the synthesis of highly versatile MIDA boronates for cross coupling reactions.
  • Synthesis of metal complexes of iminodiacetic acid with a radionuclide, especially 99mTc are as radiotracers for cholescintigraphy scans and for radiopharmaceutical applications.
  • Synthesis of lanthanide hybrid frameworks via self-assembly of lanthanide ions (Ln3+) with iminodiacetic acid under hydrothermal conditions.
  • Preparation of a thermosensitive macroporous protein-imprinted hydrogel for the recognition of protein by metal coordinate interaction.
  • Synthesis of IDA functionalized styrene-divinyl benzene co-polymeric beads for the removal of heavy metal ions like Cd(II), Cr(VI), Ni(II) and Pb(II) from their aqueous solutions.

pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Eye Irrit. 2

wgk_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Der chelateffekt.
Schwarzenbach VG.
Helvetica Chimica Acta, 35(7), 2344-2359 (1952)
Iminodiacetic acid functionalized cation exchange resin for adsorptive removal of Cr (VI), Cd (II), Ni (II) and Pb (II) from their aqueous solutions.
Misra RK.
Journal of Hazardous Materials, 185(2-3), 1508-1512 (2011)
General method for synthesis of 2-heterocyclic N-methyliminodiacetic acid boronates.
Dick GR.
Organic Letters, 12(10), 2314-2317 (2010)
Influence of the Denticity of Ligand Systems on the in vitro and in vivo Behavior of 99mTc (I)-Tricarbonyl Complexes: A Hint for the Future Functionalization of Biomolecules.
Schibli R.
Bioconjugate Chemistry, 11(3), 345-351 (2000)
Serendipity in technetium-99m dimethyl iminodiacetic acid cholescintigraphy: diagnosis of nonbiliary disorders in suspected acute cholecystitis.
Weissmann HS.
Radiology, 135(2), 449-454 (1980)

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