Iminodiacetic acid
 | |
| Names | |
|---|---|
| Preferred IUPAC name
2,2'-Azanediyldiacetic acid | |
| Other names
2-(Carboxymethylamino)acetic acid Diglycolamidic acid | |
| Identifiers | |
142-73-4  | |
| 3D model (Jmol) | Interactive image Interactive image |
| 878499 | |
| ChEBI | CHEBI:24786  |
| ChEMBL | ChEMBL461164 |
| ChemSpider | 8557 |
| ECHA InfoCard | 100.005.051 |
| EC Number | 205-555-4 |
| KEGG | C19911 |
| MeSH | imnodiacetic+acid |
| PubChem | 8897 |
| RTECS number | AI2975000 |
| |
| |
| Properties | |
| C4H7NO4 | |
| Molar mass | 133.10 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 |
−933.9–−931.3 kJ mol−1 |
| Std enthalpy of combustion (ΔcH |
−1.6430–−1.6406 MJ mol−1 |
| Hazards | |
| GHS pictograms |  |
| GHS signal word | WARNING |
| H315, H319, H335 | |
| P261, P305+351+338 | |
| EU classification (DSD) |
 Xi |
| R-phrases | R36/37/38 |
| S-phrases | S26, S36 |
| Flash point | 178 °C (352 °F; 451 K) |
| Related compounds | |
| Related alkanoic acids |
|
| 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.
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 also used in capillary electrophoresis for modulating peptide mobility.
See also
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.