Iminodiacetic acid

Iminodiacetic acid

Names
IUPAC name 2-(Carboxymethylamino)acetic acid
Other names Diglycolamidic acid
Identifiers
Beilstein Reference	878499
CAS Registry Number	142-73-4 Y
ChEBI	CHEBI:24786 N
ChEMBL	ChEMBL461164 Y
ChemSpider	8557 Y
EC number	205-555-4
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
Jmol-3D images	Image Image
KEGG	C19911 N
MeSH	imnodiacetic+acid
PubChem	8897
RTECS number	AI2975000
SMILES [o]:c(:[oH])CNCc(:[o]):[oH] OC(=O)CNCC(O)=O
Properties
Molecular 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	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 noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
N verify (what is: Y/N?)
Infobox references

Iminodiacetic acid, HN(CH₂CO₂H)₂, often abbreviated to IDA, is a dicarboxylic acid amine (note that 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.

A metal complex with the iminodiacetate anion

By capillary electrophoresis IDA is typically used for modulating peptide mobility.

See also

• HIDA scan

References