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

Description

2-Chloro-4-nitrophenyl-α-D-glucopyranoside, with the chemical name C12H14ClNO8, is a derivative of α-D-glucopyranoside, a monosaccharide, linked to a 2-chloro-4-nitrophenyl group. This off-white solid compound is utilized in various organic synthesis processes due to its unique chemical properties.

Uses

Used in Organic Synthesis:
2-Chloro-4-nitrophenyl-α-D-glucopyranoside is used as a synthetic intermediate for the preparation of various organic compounds. Its unique structure allows it to be a versatile building block in the synthesis of complex organic molecules, particularly in the fields of pharmaceuticals, agrochemicals, and specialty chemicals.
Used in Analytical Chemistry:
2-CHLORO-4-NITROPHENYL-ALPHA-D-GLUCOPYRANOSIDE can also be employed as a substrate in the study and analysis of enzymatic reactions, particularly those involving glycosidases. The cleavage of the glycosidic bond by these enzymes can be monitored, providing insights into enzyme activity, specificity, and potential applications in biotechnology and medicine.
Used in Research and Development:
In the academic and research sectors, 2-chloro-4-nitrophenyl-α-D-glucopyranoside serves as a valuable tool for probing the mechanisms of carbohydrate metabolism and the development of new methods for carbohydrate synthesis. Its reactivity and structural features make it an attractive candidate for exploring novel chemical reactions and catalysts.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, this compound may be utilized in the development of new drugs targeting carbohydrate-related diseases or as a component of drug delivery systems. Its ability to be modified and functionalized makes it a promising candidate for the design of innovative therapeutic agents.
Used in Agrochemical Industry:
2-Chloro-4-nitrophenyl-α-D-glucopyranoside can be employed in the agrochemical sector for the development of novel pesticides, herbicides, or plant growth regulators. Its unique chemical properties may contribute to the creation of more effective and environmentally friendly agricultural products.

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

• 153823-58-6 C₂₀H₂₂ClNO₁₂ 
• 619-08-9 2-chloro-4-nitrophenol 
• 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 
• 4163-65-9 per-O-acetyl-α-D-mannopyranose 
• 153823-58-6 2-chloro-4-nitrophenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 
• 153823-58-6 (2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(2-chloro-4-nitrophenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 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 

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.