17042-32-9

Basic information

• Product Name: 2,4-dinitrophenyl 2,3,4,6-tetra-O-acetylhexopyranoside
• CAS NO: 17042-32-9
• Molecular Formula: C₂₀H₂₂N₂O₁₄
• Molecular Weight: 514.3937
• Mol File: 17042-32-9.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 610°C at 760 mmHg
• Flash Point: 228.2°C
• Density: 1.47g/cm³
• Vapor Pressure: 8.04E-15mmHg at 25°C
• Refractive Index: 1.556
• CAS DataBase Reference: 2,4-dinitrophenyl 2,3,4,6-tetra-O-acetylhexopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-dinitrophenyl 2,3,4,6-tetra-O-acetylhexopyranoside(17042-32-9)
• EPA Substance Registry System: 2,4-dinitrophenyl 2,3,4,6-tetra-O-acetylhexopyranoside(17042-32-9)

Safety Data

• Hazardous Substances Data: 17042-32-9(Hazardous Substances Data)

Usage

General Description

2,4-dinitrophenyl 2,3,4,6-tetra-O-acetylhexopyranoside is a chemical compound that is commonly used in biochemical research as a reagent for detecting the presence of carbohydrates. It is a derivative of hexopyranose with four acetyl groups attached to the hydroxyl groups and a 2,4-dinitrophenyl group attached to the anomeric carbon. 2,4-dinitrophenyl 2,3,4,6-tetra-O-acetylhexopyranoside is sensitive to the presence of carbohydrates and is often used in laboratory experiments to detect the presence of sugars, such as glucose and fructose, in various samples. Its ability to react with carbohydrates and form a colored product makes it a valuable tool in carbohydrate analysis and research.

Upstream product

• 51-28-5 2,4-Dinitrophenol 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 
• 70-34-8 2,4-Dinitrofluorobenzene 
• 896-80-0 1-benzenesulfonyl-2,4-dinitro-benzene 
• 25775-97-7 2,4-dinitrophenyl β-D-glucopyranoside 
• 108-24-7 acetic anhydride 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-β-D-glucopyranose 
• 2280-44-6 D-Glucose 
• 604-69-3 β-D-glucose pentaacetate 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-α,β-D-glucopyranose 

Downstream Products

• 77516-86-0 1-O-(2,4-dinitrophenyl)-2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside 
• 25775-97-7 2,4-dinitrophenyl β-D-glucopyranoside 

Relevant articles and documents

The role of sugar substituents in glycoside hydrolysis

A series of monosubstituted deoxy and deoxyfluoro 2,4-dinitrophenyl (DNP) β-D-glycopyranosides was synthesized and used to probe the mechanism of spontaneous β-glycoside hydrolysis. Their relative rates of hydrolysis followed the order 2-deoxy > 4-deoxy > 3-deoxy ? 6-deoxy > parent > 6-deoxy- 6-fluoro > 3-deoxy-3-fluoro > 4-deoxy-4-fluoro > 2-deoxy-2-fluoro. Hammett correlations of the pH-independent hydrolysis rates of each of the 6-, 4-, 3- , and 2-position substituted glycosides with the σ1 value for the sugar ring substituent were linear (r = 0.95 to 0.999, π(I) = -2.2 to -10.7), consistent with hydrolysis rates being largely dictated by field effects on an electron-deficient transition state. The relative rates of hydrolysis of the DNP glucosides can be rationalized on the basis of the stabilities of the oxocarbenium ion-like transition states, as predicted by the Kirkwood- Westheimer model. The primary determinant of the rate of hydrolysis within a series appears to be the field effect of the ring substituent on O5, the principal center of charge development at the transition state. Differences in the rates of hydrolysis between different series of hexopyranosides may not arise solely from field effects and likely also reflect differences in steric factors or solvation.

A simplified synthesis of α-D-galactopyranose 1,3,4,6-tetraacetate

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The use of the 2,4-dinitrophenyl group in sugar chemistry re-examined

The use of the tertiary base 1,4-diazabicyclooctane, together with 1-fluoro-2,4-dinitrobenzene in the solvent DMF, proved to be an efficient method for the introduction of the 2,4-dinitrophenyl (DNP) group at different positions, including the anom