2-Nitrophenyl-beta-D-galactopyranoside

Base Information

• Chemical Name: 2-Nitrophenyl-beta-D-galactopyranoside
• CAS No.: 369-07-3
• Molecular Formula: C₁₂H₁₅NO₈
• Molecular Weight: 301.253
• Hs Code.: 29400090
• European Community (EC) Number: 206-716-1,250-286-8
• UNII: 8RFX6AT9WP
• DSSTox Substance ID: DTXSID10861907
• Nikkaji Number: J39.062C
• Wikipedia: Ortho-Nitrophenyl-%CE%B2-galactoside
• Wikidata: Q287775
• Metabolomics Workbench ID: 146537
• ChEMBL ID: CHEMBL1229648
• Mol file: 369-07-3.mol

Synonyms:2-Nitrophenyl β-D-galactopyranoside; 2-Nitrophenyl β-D-Galactopyranoside [Substrate; 2-Nitrophenyl β-D-galactopyranoside (ONPG); 2-Nitrophenyl beta-D-Galactopyranoside; 2-Nitrophenyl-β-D-Galactopyranoside; 2-Nitrophenyl-β-D-galactopyranoside; 查看更多英文别名 收起

Chemical Property of 2-Nitrophenyl-beta-D-galactopyranoside

Chemical Property:

• Appearance/Colour: White crystalline solid
• Vapor Pressure: 6.1E-14mmHg at 25°C
• Melting Point: 186-193 °C (dec.)
• Refractive Index: -68.8 ° (C=1, H2O)
• Boiling Point: 572.4 °C at 760 mmHg
• PKA: 12.69±0.70(Predicted)
• Flash Point: 300 °C
• PSA: 145.20000
• Density: 1.599 g/cm³
• LogP: -0.70330
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Water (Slightly, Heated, Sonicated)
• Water Solubility.: Soluble in water.
• XLogP3: -1.2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 3
• Exact Mass: 301.07976644
• Heavy Atom Count: 21
• Complexity: 362

Purity/Quality:

99% ^*data from raw suppliers

o-Nitrophenyl-b-D-galactopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Uses -> Biochemical Research
• Canonical SMILES: C1=CC=C(C(=C1)[N+](=O)[O-])OC2C(C(C(C(O2)CO)O)O)O
• Isomeric SMILES: C1=CC=C(C(=C1)[N+](=O)[O-])O[C@H]2[C@@H]([C@H]([C@H]([C@H](O2)CO)O)O)O
• Uses: 2-Nitrophenyl-beta-D-galactopyranoside is a β-Galactosidase substrate for colorimetric and EIA applications; counterpart of widely employed pNPP/alkaline phosphatase substrate.

Technology Process of 2-Nitrophenyl-beta-D-galactopyranoside

There total 10 articles about 2-Nitrophenyl-beta-D-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:

(2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(2-nitrophenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate (3053-17-6) → o-nitrophenyl D-galactopyranoside (2816-24-2,18249-33-7,19710-96-4,19887-85-5,56193-44-3,81132-76-5,118014-27-0,118396-84-2,369-07-3)

Guidance literature:

With methanol; barium methoxide;

DOI:10.1021/ja01165a601

Reference yield:

→ o-nitrophenyl D-galactopyranoside (2816-24-2,18249-33-7,19710-96-4,19887-85-5,56193-44-3,81132-76-5,118014-27-0,118396-84-2,369-07-3)

Guidance literature:

DOI:10.1042/bj1330089

Reference yield:

2-hydroxynitrobenzene (88-75-5,78813-12-4) → o-nitrophenyl D-galactopyranoside (2816-24-2,18249-33-7,19710-96-4,19887-85-5,56193-44-3,81132-76-5,118014-27-0,118396-84-2,369-07-3)

Guidance literature:

Multi-step reaction with 2 steps

1: TBAHS; aq. Na₂CO₃ / CH₂Cl₂ / 3 h / 20 °C

2: NaOMe; MeOH

With methanol; sodium methylate; tetra(n-butyl)ammonium hydrogensulfate; sodium carbonate; In dichloromethane;

DOI:10.1016/j.bmcl.2005.12.010

upstream raw materials:

(2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(2-nitrophenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate

2-hydroxynitrobenzene

1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside

(2R,3S,4S,5R,6R)-2-(acetoxymethyl)-6-(2-nitrophenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Downstream raw materials:

(+)-(3,5/4,6)-3,6-diazido-4-O-(β-D-galactopyranosyl)-5-hydroxycyclohexene

2-Acetamido-2-deoxy-6-O-(β-D-galactopyranosyl)-D-glucose

o-nitrophenyl 6-O-trityl-β-D-galactopyranoside

N-acetyl-D-lactosamine

Refernces

• 1、 Apparu, Maecel,Blanc-Muesser, Michele,Defaye, Jacques,Driguez, Hugues. "STEREOSELECTIVE SYNTHESES OF O- AND S-NITROPHENYL GLYCOSIDES. PART III. SYNTHESES IN THE &α-D-GALACTOPYRANOSE AND &α-MALTOSE SERIES". . p. 314 - 320. 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.