434935-69-0

Basic information

• Product Name: 2-METHYL-6-NITROBENZOIC ANHYDRIDE
• Synonyms: 6-NITRO-O-TOLUIC ANHYDRIDE;2-METHYL-6-NITROBENZOIC ANHYDRIDE;MNBA;6-Nitro-o-toluic Anhydride MNBA;2-Methyl-6-nitrobenzonic Anhydride;2-Methyl-6-nitrobenzoic anhydride 97%;2-Methyl-6-nitrobenzoic acid anhydride;2-Methyl-6-Nitrobenzoic Anhydride(MNBA)
• CAS NO: 434935-69-0
• Molecular Formula: C₁₆H₁₂N₂O₇
• Molecular Weight: 344.28
• Product Categories: Condensation & Active Esterification;Synthetic Organic Chemistry
• Mol File: 434935-69-0.mol
• Article Data: 3

Chemical Properties

• Melting Point: 177 °C
• Boiling Point: 559.436°C at 760 mmHg
• Flash Point: 246.455°C
• Appearance: /
• Density: 1.417g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.623
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: very faint turbidity in hot Toluene
• CAS DataBase Reference: 2-METHYL-6-NITROBENZOIC ANHYDRIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-METHYL-6-NITROBENZOIC ANHYDRIDE(434935-69-0)
• EPA Substance Registry System: 2-METHYL-6-NITROBENZOIC ANHYDRIDE(434935-69-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 434935-69-0(Hazardous Substances Data)

Usage

Uses

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.

General Description

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

InChI: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

Upstream product

• 40637-78-3 2-methyl-6-nitro-benzoic acid amide 
• 1885-76-3 2-cyano-3-nitrotoluene 
• 13506-76-8 2-methyl-6-nitrobenzoic acid 
• 66232-57-3 2-methyl-6-nitrobenzoyl chloride 
• 38870-89-2 Methoxyacetyl chloride 

Downstream Products

• 70275-61-5 3-phenylpropyl cyclohexanecarboxylate 
• 150272-41-6 1-methyl-3-phenylpropyl benzoate 
• 60045-26-3 3-phenylpropyl benzoate 
• 122-68-9 3-phenylpropyl (E)-3-phenyl-2-propenoate 
• 59383-43-6 allyl 2-methyl-6-nitrobenzoate 
• 15814-45-6 allyl 3-phenylpropionate 

Relevant articles and documents

2,6-Dimethyl-4-nitrobenzoic anhydride (DMNBA): An effective coupling reagent for the synthesis of carboxylic esters and lactones

Various carboxylic esters are obtained at room temperature in excellent yields with high chemoselectivities from nearly equimolar amounts of carboxylic acids and alcohols using 2,6-dimethyl-4-nitrobenzoic anhydride with triethylamine by the promotion of 4-(dimethylamino)pyridine. The efficiency of the esterification is compared to those of other dehydrations using substituted benzoic anhydrides as coupling reagents. This method was successfully applied to the synthesis of threo-aleuritic acid lactone and the desired 17-membered ring compound was prepared in high yield at room temperature from the corresponding free trihydroxycarboxylic acid using 2,6-dimethyl-4-nitrobenzoic anhydride in the presence of 4-(dimethylamino)pyridine.

A novel and efficient macrolactonization of ω-hydroxycarboxylic acids using 2-methyl-6-nitrobenzoic anhydride (MNBA)

A variety of lactones were prepared in high yields at room temperature from the corresponding ω-hydroxycarboxylic acids using 2-methyl-6-nitrobenzoic anhydride in the presence of 4-(dimethylamino)pyridine. A similar reaction also occurs with triethylamine when using a catalytic amount of 4-(dimethylamino)pyridine 1-oxide as an effective promoter for the intramolecular condensation reaction. These methods were successfully applied to the synthesis of erythro-aleuritic acid lactone and the efficiency of the cyclizations is compared to those of other reported mixed anhydride methods.