Iminodiacetic acid

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| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 408567508

| ImageFile = Iminodiacetic acid.svg

| ImageFile_Ref = {{chemboximage|correct|??}}

| ImageSize = 160

| ImageName = Skeletal formula of iminodiacetic acid

| PIN = 2,2′-Azanediyldiacetic acid

| OtherNames = 2-(Carboxymethylamino)acetic acid
Diglycolamidic acid

|Section1={{Chembox Identifiers

| CASNo = 142-73-4

| CASNo_Ref = {{cascite|correct|CAS}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = XQM2L81M8Z

| PubChem = 8897

| ChemSpiderID = 8557

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| EINECS = 205-555-4

| KEGG = C19911

| KEGG_Ref = {{keggcite|changed|kegg}}

| MeSHName = imnodiacetic+acid

| ChEBI = 24786

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 461164

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| RTECS = AI2975000

| Beilstein = 878499

| SMILES = OC(=O)CNCC(O)=O

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

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = NBZBKCUXIYYUSX-UHFFFAOYSA-N

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

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|Section2={{Chembox Properties

| C=4 | H=7 | N=1 | O=4

| Appearance = Colourless crystals

| Density = 1.436 g mL−1

| LogP = 1.84

| pKa = 1.873

| pKb = 12.124

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|Section3={{Chembox Thermochemistry

| DeltaHf = −933.9–−931.3 kJ mol−1

| DeltaHc = −1.6430–−1.6406 MJ mol−1

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|Section4={{Chembox Hazards

| GHSPictograms = {{gHS exclamation mark}}

| GHSSignalWord = WARNING

| HPhrases = {{h-phrases|315|319|335}}

| PPhrases = {{p-phrases|261|305+351+338}}

| FlashPtC = 178

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|Section5={{Chembox Related

| OtherFunction_label = alkanoic acids

| OtherFunction = {{unbulleted list|Acetylcysteine|Glycylglycine|Nitrilotriacetic acid|N-Oxalylglycine|Tiopronin|Bucillamine|Oxalyldiaminopropionic acid}}

| OtherCompounds = N-Acetylglycinamide

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Iminodiacetic acid is the organic compound with the formula HN(CH2CO2H)2, often abbreviated to IDA. A white solid, the compound is a dicarboxylic acid amine (the nitrogen atom forms a secondary amino group, not an imino group as the name suggests). IDA is a popular chelating ligand, first introduced in the early 1950s by Schwarzenbach.{{cite journal |last=Schwarzenbach |first=G |year=1952 |title=Der Chelateffekt |journal=Helv. Chim. Acta|volume=35|pages=2344–2359|doi=10.1002/hlca.19520350721 |issue=7}}

Ligand

The iminodiacetate dianion is typically a tridentate ligand, forming metal complexes by forming two, fused, five membered chelate rings. IDA thus forms stronger complexes than the bidentate ligand glycine and weaker complexes than the tetradentate ligand nitrilotriacetic acid.

File:Ferric(ida)2 anion.svg

IDA can also act as a bidentate ligand through its two carboxylate groups. Several technetium-99m complexes with bidentate IDA are used in cholescintigraphy scans (the so-called "hepatobiliary iminodiacetic acid scans") to evaluate the health and function of the gallbladder.{{cite web|url = http://www.mayoclinic.com/health/hida-scan/AN00424|title = HIDA scan (cholescintigraphy): Why is it performed?|access-date = 11 December 2007|last = Michael|first = Picco|publisher = Mayo Clinic}}{{cite book|first1 = Gerbail T.|last1 = Krishnamurthy|first2 = Shakuntala|last2 = Krishnamurthy|title = Nuclear Hepatology: A Textbook of Hepatobiliary Diseases|chapter = Imaging Agents|pages = 54–57|url = https://books.google.com/books?id=IXaPDIiGeg4C&q=iminodiacetic+acid|access-date = 19 December 2015|date = 2009|publisher = Springer|isbn = 978-3-642-00647-0}}

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.

Other applications

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.

Synthesis

A most efficient iminodiacetic synthesis dehydrogenates diethanolamine over a catalyst.{{cite patent|country=EP|number=1125633|title=Process for preparing carboxylic acids by dehydrogenating alcohols|pubdate=3 Jan 2007|assignee=Degussa AG|invent1=Monika Berweiler|invent2=Andreas Freund|invent3=Walter Girke|invent4=Matthias Höpp}}

Related compounds

References