2-Methyl-6-nitrobenzoic anhydride

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.

2-Methyl-6-nitrobenzoic anhydride

Names
Preferred IUPAC name 2-Methyl-6-nitrobenzoic anhydride
Identifiers
CAS Number	434935-69-0
3D model (JSmol)	Interactive image
ChemSpider	8648059
ECHA InfoCard	100.156.789
PubChem CID	10472648
UNII	EC8MK6FE8B 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,1-2H3 Key: YEKPNMQQSPHKBP-UHFFFAOYSA-N InChI=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,1-2H3 Key: YEKPNMQQSPHKBP-UHFFFAOYAB
SMILES CC1=C(C(=CC=C1)[N+](=O)[O-])C(=O)OC(=O)C2=C(C=CC=C2[N+](=O)[O-])C
Properties
Chemical formula	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). Infobox references

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