2-Methyl-6-nitrobenzoic anhydride
Appearance
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Names | |
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Preferred IUPAC name
2-Methyl-6-nitrobenzoic anhydride | |
Identifiers | |
3D model (
JSmol ) |
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ChemSpider | |
ECHA InfoCard
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100.156.789 |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C16H12N2O7 | |
Molar mass | 344.279 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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2-Methyl-6-nitrobenzoic anhydride is an organic acid anhydride also known as the Shiina reagent,[1][2] having a structure wherein carboxylic acids undergo intermolecular dehydration condensation. It was developed in 2002 by Prof. Isamu Shiina (Tokyo University of Science, Japan).[3] The compound is often abbreviated MNBA.
Abstract
The reagent is used for synthetic reactions wherein medium- and large-sized lactones are formed from hydroxycarboxylic acids via intramolecular ring closure (Shiina macrolactonization).[4][5] The reaction proceeds at room temperature under basic or neutral conditions. This reagent can be used not only for macrolactonization but also for esterification, amidation, and peptide coupling.
See also
- Condensation reaction
- Fischer-Speier esterification
- Mitsunobu reaction
- Shiina esterification
- Steglich esterification
- Yamaguchi esterification
References
- ^ "Named Reagents". OChemOnline. Archived from the original on 2017-09-04.
- PMID 28741352.
- .
- PMID 15058924.
- .
External links
- 2-Methyl-6-nitrobenzoic Anhydride (MNBA)
- Enantioselective Total Synthesis of Octalactin A Using Asymmetric Aldol Reactions and a Rapid Lactonization To Form a Medium-Sized Ring
- Total Synthesis of Iejimalide B. An Application of the Shiina Macrolactonization