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2,3-Dimethylmaleic anhydride acts as a reagent in the preparation of maleimides. It is also employed as an amino group protecting agent for superoxide dismutase. Further, it serves as a reactant in the dissociation of ribosomal proteins. In addition to this, it is used in the preparation of dimethylmaleic acid dimethyl ester.
Does not undergo Diels-Alder reactions with furan, but does react with 1,3-Diphenylisobenzofuran, L00101, to give benzocantharadin: J. Org. Chem., 47, 4011 (1982).
The use of the dimethylmaleoyl (DMM) group has been investigated for amino group protection in oligosaccharide synthesis. The DMM group is introduced using triethylamine as base. It promotes ß -linkage by neighboring group participation and is stable to acids and non-nucleophilic bases. Cleavage can be brought about by treatment with dilute aqueous NaOH: Eur. J. Org. Chem., 2305 (1998).
Zhang, M. H.; Gu, Z. P.; Zhang, X.; Fan, M. M. pH-sensitive ternary nanoparticles for nonviral gene delivery. RSC Adv. 2015, 5 (55), 44291-44298.
Yang, K.; Feng, L.; Liu, Z. The advancing uses of nano-graphene in drug delivery. Expert Opin. Drug Deliv. 2015, 12 (4), 601-612.
Hazard Statements: H302-H318
Harmful if swallowed. Causes serious eye damage.
Precautionary Statements: P280i-P264-P305+P351+P338-P310a-P301+P312a-P501a
Wear eye/face protection. Wash thoroughly after handling. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF SWALLOWED: Dispose of contents/container in accordance with local/regional/national/international regulations.