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Merck

681059

Sigma-Aldrich

2-Methyl-6-Nitrobenzoesäureanhydrid

97%

Synonym(e):

MNBA

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About This Item

Empirische Formel (Hill-System):
C16H12N2O7
CAS-Nummer:
Molekulargewicht:
344.28
MDL-Nummer:
UNSPSC-Code:
12352108
PubChem Substanz-ID:
NACRES:
NA.22

Qualitätsniveau

Assay

97%

Form

solid

mp (Schmelzpunkt)

173-177 °C

Funktionelle Gruppe

anhydride
ester
nitro

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

InChIKey

YEKPNMQQSPHKBP-UHFFFAOYSA-N

Allgemeine Beschreibung

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

Anwendung

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.

Piktogramme

Exclamation mark

Signalwort

Warning

Gefahreneinstufungen

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

Zielorgane

Respiratory system

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

dust mask type N95 (US), Eyeshields, Gloves


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Organic Letters, 8(21), 4955-4958 (2006)
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[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
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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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