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 Y
3D model (Jmol)	Interactive image Interactive image
Beilstein Reference	878499
ChEBI	CHEBI:24786 N
ChemSpider	8557 Y
ECHA InfoCard	100.005.051
EC Number	205-555-4
KEGG	C19911 N
MeSH	imnodiacetic+acid
PubChem CID	8897
RTECS number	AI2975000
InChI InChI=1S/C4H7NO4/c6-3(7)1-5-2-4(8)9/h5H,1-2H2,(H,6,7)(H,8,9) Y Key: NBZBKCUXIYYUSX-UHFFFAOYSA-N Y
SMILES [o]:c(:[oH])CNCc(:[o]):[oH] OC(=O)CNCC(O)=O
Properties
Chemical formula	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 (ΔfHo298)	−933.9–−931.3 kJ mol−1
Std enthalpy of combustion (ΔcHo298)	−1.6430–−1.6406 MJ mol−1
Hazards
GHS pictograms
GHS signal word	WARNING
GHS hazard statements	H315, H319, H335
GHS precautionary statements	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	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).
N  (what is YN ?)
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. 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.

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.