2-Methyl-6-nitrobenzoic anhydride

2-Methyl-6-nitrobenzoic anhydride

Names
IUPAC name (2-Methyl-6-nitrobenzoyl) 2-methyl-6-nitrobenzoate
Identifiers
CAS Number	434935-69-0
ChemSpider	8648059
Jmol 3D model	Interactive image
PubChem	10472648
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	344.28 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 a condensing agent 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).^[1] 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).^[2][3] 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
• Shiina macrolactonization
• Shiina esterification
• Fischer-Speier esterification
• Steglich esterification
• Yamaguchi esterification
• Mitsunobu reaction

References

1. 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.
2. 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. doi:10.1021/jo030367x.
3. 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. doi:10.1246/bcsj.20130216.

External links

• 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