119047-14-2

Basic information

• Product Name: 2-CHLORO-4-NITROPHENYL-ALPHA-D-GLUCOPYRANOSIDE
• Synonyms: 2-Chloro-4-nitrophenyl-D-glucopyranoside;2-Chloro-4-nitrophenyl alpha-D-glucopyranoside min. 98%
• CAS NO: 119047-14-2
• Molecular Formula: C12H14ClNO8
• Molecular Weight: 335.6945
• EINECS: 1533716-785-6
• Product Categories: Carbohydrates & Derivatives
• Mol File: 119047-14-2.mol
• Article Data: 10

Chemical Properties

• Melting Point: 127-130°C
• Boiling Point: 591.155 °C at 760 mmHg
• Flash Point: 311.32 °C
• Appearance: Off-White Solid
• Density: 1.676 g/cm³
• Refractive Index: 1.654
• Solubility: Water
• PKA: 12.57±0.70(Predicted)
• CAS DataBase Reference: 2-CHLORO-4-NITROPHENYL-ALPHA-D-GLUCOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLORO-4-NITROPHENYL-ALPHA-D-GLUCOPYRANOSIDE(119047-14-2)
• EPA Substance Registry System: 2-CHLORO-4-NITROPHENYL-ALPHA-D-GLUCOPYRANOSIDE(119047-14-2)

Safety Data

• Hazardous Substances Data: 119047-14-2(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

Uses

2-Chloro-4-nitrophenyl-α-D-glucopyranoside (cas# 119047-14-2) is a compound useful in organic synthesis.

InChI:InChI=1/C12H14ClNO8/c13-6-3-5(14(19)20)1-2-7(6)21-12-11(18)10(17)9(16)8(4-15)22-12/h1-3,8-12,15-18H,4H2/t8?,9-,10+,11+,12+/m1/s1

Upstream product

• 619-08-9 2-chloro-4-nitrophenol 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 145072-72-6 o-chloro-p-nitrophenyl β-maltotetraoside 
• 153823-58-6 C₂₀H₂₂ClNO₁₂ 
• 83-87-4 penta-O-acetyl-α-D-galactopyranose 
• 153823-58-6 (2R,3S,4S,5R,6R)-2-(acetoxymethyl)-6-(2-chloro-4-nitrophenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 604-68-2 α-D-glucopyranose peracetylate 
• 153823-58-6 2-chloro-4-nitrophenyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside 
• 118291-90-0 2-chloro-4-nitrophenol-α-D-maltotrioside 
• 492-61-5 β-D-glucose 
• 572-09-8 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide 
• 83-87-4 D-glucose pentaacetate 
• 35023-71-3 (2-chloro-4-nitrophenyl) 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 

Relevant articles and documents

Synthesis, characterization, kinetic parameters, and diagnostic application of a sensitive colorimetric substrate for β-galactosidase (2-chloro-4-nitrophenyl-β-D-galactopyranoside)

The synthesis and characterization of 2-chloro-4-nitrophenyl β-D-galactopyranoside, an improved chromogenic substrate for β-galactosidase, is described. The important kinetic parameters (Km, Vmax and Kp) for this substrate were compared with those of other substrates. The diagnostic utility of this substrate in a digoxin liposome immunoassay is discussed. The new substrate offers at least four times the sensitivity enhancement as that with ortho-nitrophenyl β-D-galactopyranoside in the assays for β-galactosidase. This substrate should find use in enzyme immunoassays where βgalactosidase is used as a label. Copyright

Binuclear copper(II) complexes discriminating epimeric glycosides and α- And β-glycosidic bonds in aqueous solution

Two chiral binuclear copper(II) complexes were synthesized and characterized for the first time as efficient chemoselective catalysts for the hydrolysis of aryl glycosides and disaccharides in aqueous solution at near neutral pH. Under these conditions, discrimination of epimeric aryl α-glycopyranosides was observed by both 29-fold different reaction rates and 3-fold different proficiency of the catalyst. Additionally, large differentiation of the nature of α- and β-glycosidic bond in aryl glycosides as model compounds is apparent, but also noted in selected disaccharides. The influence of the chirality of the complexes and the role of the configuration of the carbohydrate upon interaction with the catalyst is discussed in detail. Lastly, a putative mechanism for the metal complex-catalyzed hydrolysis is derived from the experimental evidence pointing at deprotonation of the hydroxyl group at C-2 as a pre-requisite for glycoside hydrolysis.

Evaluating N-benzylgalactonoamidines as putative transition state analogs for β-galactoside hydrolysis

Experimental evidence is provided for p-methylbenzyl-d-galactonoamidine to function as a true transition state analog for the enzymatic hydrolysis of aryl-β-d-galactopyranosides by β-galactosidase (A. oryzae). The compound exhibits inhibition constants in the low nanomolar concentration range (12-56 nM) for a selection of substrates. Along these lines, a streamlined synthetic method based on phase-transfer catalysis was optimized to afford the required variety of new aryl-β-d-galactopyranosides. Last, the stability of the galactonoamidines under the assay conditions was confirmed. This journal is the Partner Organisations 2014.