4-Nitrophenyl beta-D-glucopyranoside

Base Information

• Chemical Name: 4-Nitrophenyl beta-D-glucopyranoside
• CAS No.: 2492-87-7
• Deprecated CAS: 29857-05-4
• Molecular Formula: C12H15NO8
• Molecular Weight: 301.253
• Hs Code.: 29400090
• European Community (EC) Number: 219-661-3
• DSSTox Substance ID: DTXSID40883854
• Nikkaji Number: J191.983K
• Wikidata: Q27162435
• ChEMBL ID: CHEMBL152723
• Mol file: 2492-87-7.mol

Synonyms:4-nitrophenyl beta-D-glucoside;4-nitrophenyl beta-D-glucoside hydride;4-nitrophenyl beta-D-glucoside ion (1-);4-nitrophenylglucoside;p-nitrophenyl-beta-D-glucopyranoside;para-nitrophenyl beta-D-glucoside;PNP-beta-Glu

Chemical Property of 4-Nitrophenyl beta-D-glucopyranoside

Chemical Property:

• Appearance/Colour: White crystals
• Vapor Pressure: 2.14E-14mmHg at 25°C
• Melting Point: 165-168 °C
• Refractive Index: -102.5 ° (C=1, H2O)
• Boiling Point: 582.2 °C at 760 mmHg
• PKA: 12.55±0.70(Predicted)
• Flash Point: 305.9 °C
• PSA: 145.20000
• Density: 1.599 g/cm³
• LogP: -0.70330
• Storage Temp.: 2-8°C
• Solubility.: Methanol (Slightly, Sonicated), Water (Slightly)
• Water Solubility.: Soluble in water, methanol, warm ethanol, dimethyl sulfoxide and dimethylformamide. Insoluble in ether.
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 3
• Exact Mass: 301.07976644
• Heavy Atom Count: 21
• Complexity: 354

Purity/Quality:

98%, ^*data from raw suppliers

p-Nitrophenyl b-D-Glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi
• Statements: 20/21/22-68/20/21/22-36/37/38-68
• Safety Statements: 36/37-36-26-60-33-22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1[N+](=O)[O-])OC2C(C(C(C(O2)CO)O)O)O
• Isomeric SMILES: C1=CC(=CC=C1[N+](=O)[O-])O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
• Uses: p-Nitrophenyl β-D-Glucopyranoside (cas# 2492-87-7) is a compound useful in organic synthesis.

Technology Process of 4-Nitrophenyl beta-D-glucopyranoside

There total 25 articles about 4-Nitrophenyl beta-D-glucopyranoside which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

p-nitrophenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyde (5987-78-0) → 4-nitrophenyl-β-D-glucoside (2492-87-7)

Guidance literature:

With sodium methylate; In methanol;

DOI:10.1039/c39910000536

Reference yield: 79.0%

→ 4-nitrophenyl-β-D-glucoside (2492-87-7)

Guidance literature:

With methanol; In dichloromethane; for 0.333333h;

With sodium methylate; In dichloromethane;

Reference yield: 78.0%

D-Glucose (2280-44-6) + 4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) → 4-nitrophenyl-β-D-glucoside (2492-87-7)

Guidance literature:

D-Glucose; 4-nitro-phenol; With triethylamine; In water; at 20 ℃; for 0.166667h;

With 2-chloro-1,3-dimethylimidazolinium chloride; triethylamine; In water; at -10 ℃; for 1h;

DOI:10.1039/d0ob01727b

upstream raw materials:

p-nitrophenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyde

p-nitrophenyl 6-O-α-L-rhamnopyranosyl-β-D-glucopyranoside

4-nitrophenyl 6-O-α-L-arabinofuranosyl-β-D-glucopyranoside

C₃₇H₄₉NO₂₃

Downstream raw materials:

4-nitrophenyl β-D-galactopyranosyl-(1→4)-β-D-glucopyranoside

p-nitrophenyl β-D-galactopyranosyl-(1->6)-β-D-glucopyranoside

p-nitrophenyl 6-O-β-D-glucopyranosyl-β-D-glucopyranoside

4-nitrophenyl β-D-glucopyranosyl-(1->3)-β-D-glucopyranoside

Refernces

• 1、 Fairbanks, Antony J.. "Applications of Shoda's reagent (DMC) and analogues for activation of the anomeric centre of unprotected carbohydrates". . . Retrieved 2020/12/07.
• 2、 Fairbanks, Antony J.,Qiu, Xin. "Scope of the DMC mediated glycosylation of unprotected sugars with phenols in aqueous solution". . p. 7355 - 7365. Retrieved 2020/10/13.