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Sigma-Aldrich

2-Methyl-6-nitrobenzoic anhydride

97%

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Synonym(s):
MNBA
Empirical Formula (Hill Notation):
C16H12N2O7
CAS Number:
Molecular Weight:
344.28
MDL number:
UNSPSC Code:
12352108
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

97%

form

solid

mp

173-177 °C

SMILES string

Cc1cccc(c1C(=O)OC(=O)c2c(C)cccc2[N+]([O-])=O)[N+]([O-])=O

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

InChI key

YEKPNMQQSPHKBP-UHFFFAOYSA-N

Related Categories

General description

2-Methyl-6-nitrobenzoic anhydride is a reagent employed as a coupling promoter in the synthesis of amides, lactones, esters, and peptides.

Application

2-Methyl-6-nitrobenzoic anhydride can be used:
  • As a versatile lactonization reagent applicable in the preparation of varieties of macrolide natural products and lactones.
  • As a reaction promoter in the synthesis of carboxamide derivatives by using corresponding amines and carboxylic acids.
  • In the total synthesis of GRP78 inhibitor prunustatin A, antifungal compound (3R,16E,20E,23R)-(−)-eushearilide and an antiobestic drug tetrahydrolipstatin.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Takayuki Tonoi et al.
ACS omega, 6(5), 3571-3577 (2021-02-16)
A depsipeptidic analogue of FE399 was efficiently synthesized mainly through macrolactamization using 2-methyl-6-nitrobenzoic anhydride (MNBA), and a detailed investigation of the desired 16-membered macrolactam core of FE399 was performed. It was determined that the combination of MNBA and a catalytic
2-Methyl-6-nitrobenzoic anhydride
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2009)
Zhigang Wang et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 1061-1062, 327-333 (2017-08-08)
A new highly sensitive analytical method was developed to investigate the in vivo metabolism of albiflorin, one of the most principal components in traditional Chinese medicine. After hydrolyzation with sulfatase, the main metabolites paeonilactone A and paeonilactone B of paeoniflorin

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