2',4'-Dinitrophenyl-beta-galactopyranoside

Base Information

• Chemical Name: 2',4'-Dinitrophenyl-beta-galactopyranoside
• CAS No.: 25775-96-6
• Molecular Formula: C12H14 N2 O10
• Molecular Weight: 346.247
• DSSTox Substance ID: DTXSID30180445
• Nikkaji Number: J1.270.615D
• Wikidata: Q83050986
• Mol file: 25775-96-6.mol

Synonyms:2',4'-dinitrophenyl beta-D-galactopyranoside;2',4'-dinitrophenyl-beta-galactopyranoside;2,4-DNP-gal

Chemical Property of 2',4'-Dinitrophenyl-beta-galactopyranoside

Chemical Property:

• Vapor Pressure: 1.42E-17mmHg at 25°C
• Melting Point: 154-156°C
• Boiling Point: 646.1°Cat760mmHg
• PKA: 12.53±0.70(Predicted)
• Flash Point: 344.5°C
• PSA: 191.02000
• Density: 1.729g/cm³
• LogP: -0.27190
• Storage Temp.: Refrigerator
• Solubility.: Methanol (Slightly)
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 3
• Exact Mass: 346.06484465
• Heavy Atom Count: 24
• Complexity: 466

Purity/Quality:

97% ^*data from raw suppliers

2,4-Dinitrophenylβ-D-Galactoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C=C1[N+](=O)[O-])[N+](=O)[O-])OC2C(C(C(C(O2)CO)O)O)O
• Isomeric SMILES: C1=CC(=C(C=C1[N+](=O)[O-])[N+](=O)[O-])O[C@H]2[C@@H]([C@H]([C@H]([C@H](O2)CO)O)O)O
• Uses: These compunds have proven to be useful substrates for the study of the mechanism of action of glycosidases and related enzymes.

Technology Process of 2',4'-Dinitrophenyl-beta-galactopyranoside

There total 5 articles about 2',4'-Dinitrophenyl-beta-galactopyranoside 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: 32.0%

1-O-(2,4-dinitrophenyl)-2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside (25775-99-9) → 1-(2,4-dinitrophenyl)-β-D-galactopyranoside (25775-96-6,31046-14-7)

Guidance literature:

With methanol; acetyl chloride; at 0 - 20 ℃;

DOI:10.1021/ja992044h

Reference yield: 15.0%

D-Galactose (10257-28-0) + 2,4-Dinitrofluorobenzene (70-34-8,65727-75-5) → 1-(2,4-dinitrophenyl)-β-D-galactopyranoside (25775-96-6,31046-14-7)

Guidance literature:

With sodium hydrogencarbonate; In ethanol; at 20 ℃;

DOI:10.1016/00404-0399(50)1031C-

Reference yield:

2,3,4,6-tetra-O-acetyl-α/β-D-galactopyranose (3947-62-4,6207-76-7,10343-06-3,19235-21-3,22554-70-7,22860-22-6,57884-82-9,62057-79-8,70191-05-8,109525-54-4,140147-37-1,47339-09-3) → 1-(2,4-dinitrophenyl)-β-D-galactopyranoside (25775-96-6,31046-14-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 1,4-diazabicyclo[2.2.2]octane / dimethylformamide / 20 °C

1.2: 63 percent / dimethylformamide / 20 °C

2.1: 32 percent / acetyl chloride; methanol / 0 - 20 °C

With 1,4-diaza-bicyclo[2.2.2]octane; methanol; acetyl chloride; In N,N-dimethyl-formamide; 1.1: deprotonation / 1.2: Substitution / 2.1: Deacetylation;

DOI:10.1021/ja992044h

upstream raw materials:

D-Galactose

2,4-Dinitrofluorobenzene

1-O-(2,4-dinitrophenyl)-2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside

2,3,4,6-tetra-O-acetyl-α/β-D-galactopyranose

Downstream raw materials:

4-nitrophenyl 1,4-β-D-thiogalactobioside

Refernces

• 1、 Sharma, Sunil K.,Corrales, Guillermo,Penades, Soledad. "Single step stereoselective synthesis of unprotected 2,4-dinitrophenyl glycosides". . p. 5627 - 5630. Retrieved 2007/10/02.
• 2、 Sinnott,Souchard. "The mechanism of action of beta-galactosidase. Effect of aglycone nature and -deuterium substitution on the hydrolysis of aryl galactosides.". . p. 89 - 98. Retrieved 2007/10/04.