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Other names N-(Carboxymethyl)-N-methyl-glycine | |
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3D model (JSmol) | |
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ChemSpider | |
ECHA InfoCard | 100.022.326 |
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Properties | |
Chemical formula | C5H9NO4 |
Molar mass | 147.130 g·mol |
Appearance | white solid |
Melting point | 223–225 °C (433–437 °F; 496–498 K) |
Hazards | |
GHS labelling: | |
Pictograms | |
Signal word | Warning |
Hazard statements | H315, H319, H335 |
Precautionary statements | 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 , 100 kPa). Infobox references |
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. It is a component of organoboron reagents as well.
Synthesis and reaction
It is prepared from imidodiacetic acid by N-methylation using the Eschweiler–Clarke reaction:
MIDA boronates are derivatives with the formula CH3N(CH2CO2)2BR, where R is a cross-coupling partner.
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). 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.