N-Methyliminodiacetic acid
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| Names | |
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| Other names
N-(Carboxymethyl)-N-methyl-glycine
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| Identifiers | |
3D model (JSmol)
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| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.022.326 |
| EC Number |
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PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C5H9NO4 | |
| Molar mass | 147.130 g·mol−1 |
| Appearance | white solid |
| Melting point | 223–225 °C (433–437 °F; 496–498 K) |
| Hazards | |
| GHS labelling:[1] | |
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| Warning | |
| H315, H319, H335 | |
| P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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N-Methyliminodiacetic acid is an organic compound with the formula CH3N(CH2CO2H)2. It is a white solid, which as its conjugate base CH3N(CH2CO−2)2 is used as a chelating agent for iron.[2] It is a component of organoboron reagents as well.[3]
Synthesis and reaction
It is prepared from imidodiacetic acid by N-methylation using the Eschweiler–Clarke reaction:[4]
MIDA boronates are derivatives with the formula CH3N(CH2CO2)2BR, where R is a cross-coupling partner.[5]
Related compounds
- Imidodiacetic acid (IDA)
- N-(2-Carboxyethyl)iminodiacetic acid
- Nitrilotriacetic acid (NTA)
- N-Hydroxyiminodiacetic acid (HIDA), HON(CH2CO2H)2 (registry number = 87339–38–6).[6] See HIDA scan.
References
- ^ "N-Methyliminodiacetic acid". pubchem.ncbi.nlm.nih.gov.
- ^ Lovley, D. R.; Woodward, J. C.; Chapelle, F. H. (1996). "Rapid Anaerobic Benzene Oxidation with a Variety of Chelated Fe(III) Forms". Applied and Environmental Microbiology. 62 (1): 288–291. Bibcode:1996ApEnM..62..288L. doi:10.1128/aem.62.1.288-291.1996. PMC 1388759. PMID 16535218.
- ^ Dailey, Ian; Burke, Martin D. (2010). "N -(Carboxymethyl)- N -methyl-glycine". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rn01228.pub2. ISBN 978-0471936237.
- ^ Ballmer, Steven G.; Gillis, Eric P.; Burke, Martin D. (2009). "B-Protected Haloboronic Acids for Iterative Cross-Coupling". Organic Syntheses. 86: 344. doi:10.15227/orgsyn.086.0344.
- ^ "MIDA Boronates".
- ^ Hubregtse, Ton; Hanefeld, Ulf; Arends, Isabel W. C. E. (2007). "Stabilizing Factors for Vanadium(IV) in Amavadin". European Journal of Organic Chemistry. 2007 (15): 2413–2422. doi:10.1002/ejoc.200601053.