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
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.156.789
UNII
  • 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
  • CC1=C(C(=CC=C1)[N+](=O)[O-])C(=O)OC(=O)C2=C(C=CC=C2[N+](=O)[O-])C
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).
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

References
  1. "Named Reagents". OChemOnline. Archived from the original on 2017-09-04.
  2. 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.
  3. 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.
  4. 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.
  5. 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.


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