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Revision as of 10:55, 18 January 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: ChEMBL.← Previous edit Latest revision as of 14:28, 7 July 2024 edit undoAlistair1978 (talk | contribs)Extended confirmed users35,879 editsm typo 
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{{chembox {{chembox
| Verifiedfields = changed
| Watchedfields = changed | Watchedfields = changed
| verifiedrevid = 396495109 | verifiedrevid = 408567508
| ImageFile = Iminodiacetic acid.png | ImageFile = Iminodiacetic acid.svg
| ImageFile_Ref = {{chemboximage|correct|??}}
| ImageSize = | ImageSize = 160
| IUPACName = 2-(carboxymethylamino)acetic acid
| ImageName = Skeletal formula of iminodiacetic acid
| OtherNames = Diglycolamidic acid
| PIN = 2,2′-Azanediyldiacetic acid
⚫ | Section1={{Chembox Identifiers
| OtherNames = 2-(Carboxymethylamino)acetic acid<br />Diglycolamidic acid
| InChI = 1/C4H7NO4/c6-3(7)1-5-2-4(8)9/h5H,1-2H2,(H,6,7)(H,8,9)
⚫ |Section1={{Chembox Identifiers
| InChIKey = NBZBKCUXIYYUSX-UHFFFAOYAF
⚫ | 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 = 461164
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | 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 = 1S/C4H7NO4/c6-3(7)1-5-2-4(8)9/h5H,1-2H2,(H,6,7)(H,8,9)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = NBZBKCUXIYYUSX-UHFFFAOYSA-N | StdInChIKey = NBZBKCUXIYYUSX-UHFFFAOYSA-N
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
⚫ | CASNo = 142-73-4
⚫ }}
⚫ | CASNo_Ref = {{cascite|correct|CAS}}
⚫ |Section2={{Chembox Properties
⚫ | EC-number = 205-555-4
| PubChem = 8897 | C=4 | H=7 | N=1 | O=4
| Appearance = Colourless crystals
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫ | Density = 1.436 g mL<sup>−1</sup>
⚫ | ChemSpiderID = 8557
| LogP = 1.84
⚫ | SMILES = O=C(O)CNCC(=O)O
| pKa = 1.873
| pKb = 12.124
⚫ }}
⚫ |Section3={{Chembox Thermochemistry
| DeltaHf = −933.9–−931.3 kJ mol<sup>−1</sup>
| DeltaHc = −1.6430–−1.6406 MJ mol<sup>−1</sup>
}}
|Section4={{Chembox Hazards
| GHSPictograms = {{gHS exclamation mark}}
| GHSSignalWord = '''WARNING'''
| HPhrases = {{h-phrases|315|319|335}}
| PPhrases = {{p-phrases|261|305+351+338}}
| FlashPtC = 178
}}
|Section5={{Chembox Related
| OtherFunction_label = alkanoic acids
| OtherFunction = {{unbulleted list|]|]|]|]|]|]|]}}
| OtherCompounds = ]
}} }}
⚫ | Section2={{Chembox Properties
| C = 4 | H = 7 | N = 1 | O = 4
| Appearance =
⚫ | Density = 1.436 g/cm<sup>3</sup>
| MeltingPt = 247.5 °C
| BoilingPt =
| Solubility =
⚫ }}
⚫ | Section3 = {{Chembox Hazards
| EUIndex = not listed
| FlashPt = 178 °C
| Autoignition =
⚫ }}
}} }}


'''Iminodiacetic acid''', HN(CH<sub>2</sub>CO<sub>2</sub>H)<sub>2</sub>, often abbreviated to '''IDA''', is an ]. The iminodiacetate anion can act as a ] ] to form a metal complex with two, fused, five membered ] rings.<ref>{{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}}</ref> The proton on the nitrogen atom can be replaced by a carbon atom of a polymer to create an ], such as ]. '''Iminodiacetic acid''' is the ] with the formula HN(CH<sub>2</sub>CO<sub>2</sub>H)<sub>2</sub>, often abbreviated to '''IDA'''. A white solid, the compound is a ] ] (the nitrogen atom forms a secondary amino group, not an ] group as the name suggests). The iminodiacetate dianion is a ] ], forming metal complexes by forming two, fused, five membered ] rings.<ref name=AnnieP/> The proton on the nitrogen atom can be replaced by a carbon atom of a polymer to create an ], such as ]. Complexes of IDA and EDTA were introduced in the early 1950s by Schwarzenbach.<ref>{{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}}</ref>


]
IDA forms stronger complexes than the bidentate ligand ] and weaker complexes than the tetradentate ligand ].
IDA forms stronger complexes than the bidentate ligand ] and weaker complexes than the tetradentate ligand ]. It can also act as a bidentate ligand through its two carboxylate groups. Several ] complexes are used in ] scans (also known as ''hepatobiliary iminodiacetic acid scans'') to evaluate the health and function of the ].<ref>{{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 = ]}}</ref><ref>{{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 = ]|isbn = 978-3-642-00647-0}}</ref>
]{{clear-left}}


Iminodiacetic acid is an important intermediate in one of the two main industrial processes used to manufacture the herbicide ]. It is used in ] for modulating ]. It is also used as a precursor for the manufacture of the ] ].
==See also==

* ]
==Related compounds==
* ] (MIDA)
* ]
* ] (NTA)
* N-hydroxyiminodiacetic acid (HIDA), {{chem2|HON(CH2CO2H)2}} (] = 87339-38-6)<ref>{{cite journal |doi=10.1002/ejoc.200601053 |title=Stabilizing Factors for Vanadium(IV) in Amavadin |date=2007 |last1=Hubregtse |first1=Ton |last2=Hanefeld |first2=Ulf |last3=Arends |first3=Isabel W. C. E. |journal=European Journal of Organic Chemistry |volume=2007 |issue=15 |pages=2413–2422 }}</ref> See ].


==References== ==References==
{{reflist}} {{Reflist}}


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