13331-27-6 | 3-Nitrophenylboronic acid

Packsize	Purity	Availability	Price	Discounted Price
1g	98%	in stock	$9.00	$6.00
5g	98%	in stock	$10.00	$7.00
50g	98%	in stock	$19.00	$13.00
100g	98%	in stock	$36.00	$25.00

Description

• Catalog Number: AA52426
• Chemical Name: 3-Nitrophenylboronic acid
• CAS Number: 13331-27-6
• Molecular Formula: C6H6BNO4
• Molecular Weight: 166.9271
• MDL Number: MFCD00007193
• SMILES: OB(c1cccc(c1)[N+](=O)[O-])O

Computed Properties

• Complexity: 169
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 12
• Hydrogen Bond Acceptor Count: 4
• Hydrogen Bond Donor Count: 2
• Rotatable Bond Count: 1

Upstream Synthesis Route

3-Nitrophenylboronic acid is a versatile compound widely used in chemical synthesis for its unique properties. This compound serves as a key building block in organic chemistry, specifically in the field of cross-coupling reactions. By forming stable boronate esters with aryl halides or triflates, 3-Nitrophenylboronic acid facilitates the creation of complex molecular structures. Additionally, it is employed in the synthesis of pharmaceuticals, agrochemicals, and materials science due to its ability to act as a valuable intermediate in various transformations. With its strategic role in the production of diverse compounds, 3-Nitrophenylboronic acid continues to be a valuable asset in the realm of chemical synthesis.

Literature

• Nitrophenylboronic acids as highly chemoselective probes to detect hydrogen peroxide in foods and agricultural products.

  Journal of agricultural and food chemistry 20111109

• Direct analysis of polyols using 3-nitrophenylboronic acid in capillary electrophoresis: thermodynamic and electrokinetic principles of molecular recognition.

  Analytical and bioanalytical chemistry 20101001

• Phenylboronic-acid-based carbohydrate binders as antiviral therapeutics: monophenylboronic acids.

  Antiviral chemistry & chemotherapy 20100811

• Structural study of phenyl boronic acid derivatives as AmpC beta-lactamase inhibitors.

  Bioorganic & medicinal chemistry letters 20100601

• Boronic acid catalyzed ene carbocyclization of acetylenic dicarbonyl compounds.

  Chemical communications (Cambridge, England) 20100407

• Synthesis and evaluation of 3-(dihydroxyboryl)benzoic acids as D,D-carboxypeptidase R39 inhibitors.

  Journal of medicinal chemistry 20091008

• A pharmacological MRI assessment of dizocilpine (MK-801) in the 3-nitroproprionic acid-lesioned rat.

  Neuroscience letters 20081017

• Kinetic evidence for high reactivity of 3-nitrophenylboronic acid compared to its conjugate boronate ion in reactions with ethylene and propylene glycols.

  Inorganic chemistry 20080303

• Electrokinetic probes for single-step screening of polyol stereoisomers: the virtues of ternary boronate ester complex formation.

  Chemical communications (Cambridge, England) 20080121

• Aminophenyl- and nitrophenyl-labeled nucleoside triphosphates: synthesis, enzymatic incorporation, and electrochemical detection.

  Angewandte Chemie (International ed. in English) 20080101

• Structures of carbohydrate-boronic acid complexes determined by NMR and molecular modelling in aqueous alkaline media.

  Organic & biomolecular chemistry 20040521

• 3-Methoxycarbonyl-5-nitrophenyl boronic acid: high affinity diol recognition at neutral pH.

  Bioorganic & medicinal chemistry letters 20040105

• Inhibition of the enzymatic activity of prostate-specific antigen by boric acid and 3-nitrophenyl boronic acid.

  The Prostate 20030101

• Structure-based approach for binding site identification on AmpC beta-lactamase.

  Journal of medicinal chemistry 20020718

• Parallel synthesis of oxazolines and thiazolines by tandem condensation-cyclodehydration of carboxylic acids with amino alcohols and aminothiols.

  Journal of combinatorial chemistry 20020101