3-Methoxycarbonyl-5-nitrophenylboronic acid

• CAS: 117342-20-8
• Catalog Number: ACM117342208
• Category: Main Products
• Molecular Weight: 224.96
• Molecular Formula: C8H8BNO6
• Synonyms: 3-METHOXYCARBONYL-5-NITROPHENYLBORONIC ACID; (3-(Methoxycarbonyl)-5-nitrophenyl)boronic acid; 3-Methoxycarbonyl-5-nitrobenzeneboronic acid; 3-Methoxycarbonyl-5-nitrophenylboronic acid
• IUPAC Name: (3-methoxycarbonyl-5-nitrophenyl)boronicacid
• SMILES: B(C1=CC(=CC(=C1)[N+](=O)[O-])C(=O)OC)(O)O
• InChI Key: CDGIRLKQNJXHBJ-UHFFFAOYSA-N
• Boiling Point: 445.9ºC at 760 mmHg
• Melting Point: 250-255ºC
• Flash Point: 223.5ºC
• Density: 1.45g/cm³
• Exact Mass: 225.04400
• Hazard Statements: Xi: Irritant
• Safety Description: 26-36/37/39-36

Case Study

3-Methoxycarbonyl-5-Nitrophenylboronic Acid for Diol Recognition

Hormuzd R. Mulla, et al. Bioorganic & medicinal chemistry letters, 2004, 14(1), 25-27.

Several boronic acids were screened for their ability to bind to diols, and the results showed that 3-methoxycarbonyl-5-nitrophenylboronic acid (compound 5) binds to catechol dyes and fructose with an affinity comparable to ortho-methylamino-substituted boronic acids. Furthermore, the 3-methoxycarbonyl-5-nitrophenylboronic acid recognition module can be attached to various receptor scaffolds to synthesize sugar-specific sensors.
Determination and analysis of binding constants
· Using a fluorometric method, the binding constants of boronic acids 1-9 and alizarin red S (ARS, 10) were determined. The fluorescence of ARS increases significantly when it binds, making it a useful spectroscopic tool for determining association constants. By monitoring the fluorescence of ARS as boronic acid concentration increases, the binding constant (Ka) was calculated using the Benesi-Hildebrand method.
· To determine the binding of fructose with 5 and 2, a competition assay was conducted using ARS as the indicator. As fructose concentrations were added to a solution of the highly fluorescent boronic acid.ARS complex, the bound ARS was displaced, leading to a decrease in fluorescence. The binding constant between boronic acid and fructose was then calculated using standard methods, with 5 showing a Ka value of 135±270 M-1 and 2 with a Ka of 164±330 M-1. Besides, the addition of electron withdrawing groups to an arylboronic acid can enhance sugar-binding similar to the ortho benzylamine functionality.

Custom Reviews

August 11, 2023

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Custom Q&A

What is the molecular formula of 3-Methoxycarbonyl-5-nitrophenylboronic acid?

The molecular formula is C8H8BNO6.

What is the molecular weight of 3-Methoxycarbonyl-5-nitrophenylboronic acid?

The molecular weight is 224.97 g/mol.

What is the IUPAC name of 3-Methoxycarbonyl-5-nitrophenylboronic acid?

The IUPAC name is (3-methoxycarbonyl-5-nitrophenyl)boronic acid.

What is the InChI key of 3-Methoxycarbonyl-5-nitrophenylboronic acid?

The InChI key is CDGIRLKQNJXHBJ-UHFFFAOYSA-N.

What is the canonical SMILES of 3-Methoxycarbonyl-5-nitrophenylboronic acid?

The canonical SMILES is B(C1=CC(=CC(=C1)[N+](=O)[O-])C(=O)OC)(O)O.

What is the CAS number of 3-Methoxycarbonyl-5-nitrophenylboronic acid?

The CAS number is 117342-20-8.

What is the European Community (EC) number of 3-Methoxycarbonyl-5-nitrophenylboronic acid?

The EC number is 833-747-3.

What is the ChEMBL ID of 3-Methoxycarbonyl-5-nitrophenylboronic acid?

The ChEMBL ID is CHEMB88902.

What is the hydrogen bond donor count of 3-Methoxycarbonyl-5-nitrophenylboronic acid?

The hydrogen bond donor count is 2.

What is the hydrogen bond acceptor count of 3-Methoxycarbonyl-5-nitrophenylboronic acid?

The hydrogen bond acceptor count is 6.