63299-56-9

Basic information

• Product Name: Benzoic acid, 4-fluoro-3,5-dinitro-, methyl ester
• CAS NO: 63299-56-9
• Molecular Formula: C8H5FN2O6
• Molecular Weight: 244.136
• Mol File: 63299-56-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Benzoic acid, 4-fluoro-3,5-dinitro-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid, 4-fluoro-3,5-dinitro-, methyl ester(63299-56-9)
• EPA Substance Registry System: Benzoic acid, 4-fluoro-3,5-dinitro-, methyl ester(63299-56-9)

Safety Data

• Hazardous Substances Data: 63299-56-9(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 2365-73-3 4-fluoro-3,5-dinitro-benzoyl chloride 
• 2365-71-1 3,5-dinitro-4-fluorobenzoic acid 
• 2552-45-6 methyl 4-chloro-3,5-dinitrobenzoate 

Downstream Products

• 367946-85-8 2,6-dinitro-4-(methoxycarbonyl)phenyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 
• 367947-05-5 2,6-dinitro-4-(methoxycarbonyl)phenyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 
• 6156-95-2 3.5-Dinitro-4-phenylamino-benzoesaeure-methylester 

Relevant articles and documents

A new, efficient glycosylation method for oligosaccharide synthesis under neutral conditions: Preparation and use of new DISAL donors

Efficient, stereoselective glycosylation methods are required for the synthesis of complex oligosaccharides as tools in glycobiology. All glycosylation methods, which have found wide acceptance, rely on Lewis acid activation of glycosyl donors prior to glycosylation. Here, we present a new and efficient method for glycosylation under neutral or mildly basic conditions. Glycosides of methyl 2-hydroxy-3,5-dinitrobenzoate (DISAL) and its para regioisomer, methyl 4-hydroxy-3,5-dinitrobenzoate, were prepared by nucleophilic aromatic substitution. In a first demonstration of their potential as glycosyl donors, stereospecific glycosylation of methanol was achieved. In the glycosylation of more hindered alcohols, the β-donor proved more reactive, and α-glucosides were predominantly formed. Glycosylation of protected monosaccharides, with free 6-0H or 3-OH, proceeded smoothly in 1-methyl-2-pyrrolidinone (NMP) at 40-60 °C in the absence of Lewis acids and bases in good to excellent yields. Glycosylation of 3-OH gave the α-linked disaccharide only.