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681059

Sigma-Aldrich

2-Methyl-6-nitrobenzoic anhydride

97%

Synonym(s):

MNBA

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About This Item

Empirical Formula (Hill Notation):
C16H12N2O7
CAS Number:
434935-69-0
Molecular Weight:
344.28
MDL number:
MFCD06797117
UNSPSC Code:
12352108
PubChem Substance ID:
24885612
NACRES:
NA.22

Quality Level

200

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

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
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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The first total synthesis of (-) and (+)-2-hydroxy-24-oxooctacosanolide using an effective lactonization
Shiina I, et al.
Organic Letters, 8(21), 4955-4958 (2006)
Isamu Shiina et al.
Organic letters, 8(21), 4955-4958 (2006-10-06)
[structure: see text] An effective method for the total synthesis of 2-hydroxy-24-oxooctacosanolide, a defensive salivary secretion of the African termite Pseudacanthotermes spiniger, has been developed. The key lactonization to form a 29-membered ring lactone core is performed using 2-methyl-6-nitrobenzoic anhydride
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
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
Ryohei Hirano et al.
Journal of mass spectrometry : JMS, 53(8), 665-674 (2018-05-17)
CYP3A phenotyping provides a means for personalized drug therapy. We focused our attention on the plasma 6β-hydroxycortisol (6β-OHF) to cortisol ratio as an index for CYP3A phenotyping. In the present study, we developed a sensitive and reliable method for the
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