2-Methyl-6-nitrobenzoic anhydride

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 ;
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

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.

^ "Named Reagents". OChemOnline. Archived from the original on 2017-09-04.
^ Yahata, K.; Ye, N.; Iso, K.; Naini, S. R.; Yamashita, S.; Ai, Y.; Kishi, Y. (2017). "Unified Synthesis of Right Halves of Halichondrins A–C". J. Org. Chem. 82 (17): 8792–8807. doi:10.1021/acs.joc.7b01283. PMID 28741352.
^ Shiina, I.; Ibuka, R.; Kubota, M. (2002). "A New Condensation Reaction for the Synthesis of Carboxylic Esters from Nearly Equimolar Amounts of Carboxylic Acids and Alcohols Using 2-Methyl-6-nitrobenzoic Anhydride". Chem. Lett. 31 (3): 286. doi:10.1246/cl.2002.286.
^ Shiina, I.; Kubota, M.; Oshiumi, H.; Hashizume, M. (2004). "An Effective Use of Benzoic Anhydride and Its Derivatives for the Synthesis of Carboxylic Esters and Lactones: A Powerful and Convenient Mixed Anhydride Method Promoted by Basic Catalysts". J. Org. Chem. 69 (6): 1822–30. doi:10.1021/jo030367x. PMID 15058924.
^ Shiina, I. (2014). "An Adventurous Synthetic Journey with MNBA from Its Reaction Chemistry to the Total Synthesis of Natural Products". Bull. Chem. Soc. Jpn. 87 (2): 196–233. doi:10.1246/bcsj.20130216.

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