Iminodiacetic acid

Iminodiacetic acid
Names
	Preferred IUPAC name 2,2'-Azanediyldiacetic acid
	Other names 2-(Carboxymethylamino)acetic acid; Diglycolamidic acid
Identifiers
CAS Number	142-73-4 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	878499
ChEBI	CHEBI:24786 ;
ChEMBL	ChEMBL461164 ;
ChemSpider	8557 ;
ECHA InfoCard	100.005.051
EC Number	205-555-4;
KEGG	C19911 ;
MeSH	imnodiacetic+acid
PubChem CID	8897;
RTECS number	AI2975000;
CompTox Dashboard (EPA)	DTXSID2027098 ;
	InChI InChI=1S/C4H7NO4/c6-3(7)1-5-2-4(8)9/h5H,1-2H2,(H,6,7)(H,8,9) Key: NBZBKCUXIYYUSX-UHFFFAOYSA-N ;
	SMILES OC(=O)CNCC(O)=O;
Properties
Chemical formula	C4H7NO4
Molar mass	133.103 g·mol−1
Appearance	Colourless crystals
Density	1.436 g mL−1
log P	1.84
Acidity (pKa)	1.873
Basicity (pKb)	12.124
Thermochemistry
Std enthalpy of; formation (ΔfH⦵298)	−933.9–−931.3 kJ mol−1
Std enthalpy of; combustion (ΔcH⦵298)	−1.6430–−1.6406 MJ mol−1
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P305+P351+P338
Flash point	178 °C (352 °F; 451 K)
Related compounds
Related alkanoic acids	Acetylcysteine; Glycylglycine; Nitrilotriacetic acid; N-Oxalylglycine; Tiopronin; Bucillamine; Oxalyldiaminopropionic acid;
Related compounds	N-Acetylglycinamide
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Iminodiacetic acid, HN(CH₂CO₂H)₂, often abbreviated to IDA, is a dicarboxylic acid amine (the nitrogen atom forms a secondary amino group, not an imino group as the name suggests). The iminodiacetate anion can act as a tridentate ligand to form a metal complex with two, fused, five membered chelate rings.^[1] The proton on the nitrogen atom can be replaced by a carbon atom of a polymer to create an ion-exchange resin, such as chelex 100.

A tridentate metal complex with the iminodiacetate anion

IDA forms stronger complexes than the bidentate ligand glycine and weaker complexes than the tetradentate ligand nitrilotriacetic acid. It can also act as a bidentate ligand through its two carboxylate groups. Several technetium-99m complexes are used in cholescintigraphy scans (also known as hepatobiliary iminodiacetic acid scans) to evaluate the health and function of the gallbladder.^[2]^[3]

Iminodiacetic acid is an important intermediate in one of the two main industrial processes used to manufacture the herbicide glyphosate. It is used in capillary electrophoresis for modulating peptide mobility. It is also used as a precursor for the manufacture of the indicator xylenol orange.

References

^ Schwarzenbach, G (1952). "Der Chelateffekt". Helv. Chim. Acta. 35 (7): 2344–2359. doi:10.1002/hlca.19520350721.
^ Michael, Picco. "HIDA scan (cholescintigraphy): Why is it performed?". Mayo Clinic. Retrieved 11 December 2007.
^ Krishnamurthy, Gerbail T.; Krishnamurthy, Shakuntala (2009). "Imaging Agents". Nuclear Hepatology: A Textbook of Hepatobiliary Diseases. Springer. pp. 54–57. ISBN 978-3-642-00647-0. Retrieved 19 December 2015.

[1] Schwarzenbach, G (1952). "Der Chelateffekt". Helv. Chim. Acta. 35 (7): 2344–2359. doi:10.1002/hlca.19520350721.

[2] Michael, Picco. "HIDA scan (cholescintigraphy): Why is it performed?". Mayo Clinic. Retrieved 11 December 2007.

[3] Krishnamurthy, Gerbail T.; Krishnamurthy, Shakuntala (2009). "Imaging Agents". Nuclear Hepatology: A Textbook of Hepatobiliary Diseases. Springer. pp. 54–57. ISBN 978-3-642-00647-0. Retrieved 19 December 2015.

[1]

[2]

[3]

See also

References