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2-Methyl-6-nitrobenzoic anhydride

Column 1Column 2
Preferred IUPAC name
2-Methyl-6-nitrobenzoic anhydride
CAS Number.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}434935-69-0
3D model (JSmol)Interactive image
ChemSpider8648059
ECHA InfoCard100.156.789
PubChem CID10472648
UNIIEC8MK6FE8B Y
CompTox Dashboard (EPA)DTXSID60440549
InChI
InChI=1S/C16H12N2O7/c1-9-5-3-7-11(17(21)22)13(9)15(19)25-16(20)14-10(2)6-4-8-12(14)18(23)24/h3-8H,1-2H3Key: YEKPNMQQSPHKBP-UHFFFAOYSA-NInChI=1/C16H12N2O7/c1-9-5-3-7-11(17(21)22)13(9)15(19)25-16(20)14-10(2)6-4-8-12(14)18(23)24/h3-8H,1-2H3Key: YEKPNMQQSPHKBP-UHFFFAOYAB
SMILES
CC1=C(C(=CC=C1)N+[O-])C(=O)OC(=O)C2=C(C=CC=C2N+[O-])C
Chemical formulaC16H12N2O7
Molar mass344.279 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Infobox references | |

2-Methyl-6-nitrobenzoic anhydride is an organic acid anhydride also known as the Shiina reagent, having a structure wherein carboxylic acids undergo intermolecular dehydration condensation. It was developed in 2002 by Prof. Isamu Shiina (Tokyo University of Science, Japan). The compound is often abbreviated MNBA.

The reagent is used for synthetic reactions wherein medium- and large-sized lactones are formed from hydroxycarboxylic acids via intramolecular ring closure (Shiina macrolactonization). 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.

  • Condensation reaction

  • Fischer-Speier esterification

  • Mitsunobu reaction

  • Shiina esterification

  • Steglich esterification

  • Yamaguchi esterification

  • 2-Methyl-6-nitrobenzoic Anhydride (MNBA) doi:10.1002/047084289X.rn00956

  • Enantioselective Total Synthesis of Octalactin A Using Asymmetric Aldol Reactions and a Rapid Lactonization To Form a Medium-Sized Ring doi:10.1002/chem.200500417

  • Total Synthesis of Iejimalide B. An Application of the Shiina Macrolactonization doi:10.1021/ol702129w

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