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681059

Sigma-Aldrich

2-Methyl-6-nitrobenzoic anhydride

97%

Synonyme(s) :

MNBA

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About This Item

Formule empirique (notation de Hill):
C16H12N2O7
Numéro CAS:
434935-69-0
Poids moléculaire :
344.28
Numéro MDL:
MFCD06797117
Code UNSPSC :
12352108
ID de substance PubChem :
24885612
Nomenclature NACRES :
NA.22

Pureté

97%

Forme

solid

Pf

173-177 °C

Chaîne SMILES 

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

Clé InChI

YEKPNMQQSPHKBP-UHFFFAOYSA-N

Description générale

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.

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H315,H319,H335

Classification des risques

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

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

Certificats d'analyse (COA)

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2-Methyl-6-nitrobenzoic anhydride
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2009)
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)
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Molecules (Basel, Switzerland), 26(4) (2021-02-12)
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Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 1061-1062, 327-333 (2017-08-08)
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