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Thermo Scientific Chemicals
4-Nitrobenzeneboronic acid, 95%
CAS: 24067-17-2 | C6H6BNO4 | 166.93 g/mol
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Chemical Identifiers
CAS24067-17-2
IUPAC Name(4-nitrophenyl)boronic acid
Molecular FormulaC6H6BNO4
InChI KeyNSFJAFZHYOAMHL-UHFFFAOYSA-N
SMILESOB(O)C1=CC=C(C=C1)[N+]([O-])=O
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Specifications
Specification Sheet
Specification SheetFormCrystals or powder or crystalline powder
Assay from Supplier's CofA≥94.0% (U.S. specification)
Appearance (Color)Cream to yellow to pale brown
Assay (Aqueous acid-base Titration)≥94.0% (U.K. specification)
Proton NMRConforms to structure (U.K. specification)
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It is reagent used forligand-free palladium-catalyzed Suzuki-Miyaura cross-couplings, ruthenium catalyzed direct arylation of benzylic sp3 carbons of acyclic amines, Diels-Alder or C-H activation reactions, regioselective Suzuki-Miyaura coupling and tandem palladium-catalyzed intramolecular aminocarbonylation and annulations, N-arylation of phenylurea using copper acetylacetonate catalyst, environmentally benign one-pot synthesis through a double arylation process, copper-mediated cyanation, copper-catalyzed arylations regioselective glycosylations. Suzuki couplings followed by arylations, X-ray absorption on rhodium-grafted hydrotalcite catalyst for heterogeneous 1,4-addition reaction of organoboron reagents to electron deficient olefins. It is used in Preparation of combretastatin analogs as potential antitumor agents and human immunodeficiency virus (HIV) protease inhibitors with antiviral activities against drug-resistant viruses
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
Applications
It is reagent used forligand-free palladium-catalyzed Suzuki-Miyaura cross-couplings, ruthenium catalyzed direct arylation of benzylic sp3 carbons of acyclic amines, Diels-Alder or C-H activation reactions, regioselective Suzuki-Miyaura coupling and tandem palladium-catalyzed intramolecular aminocarbonylation and annulations, N-arylation of phenylurea using copper acetylacetonate catalyst, environmentally benign one-pot synthesis through a double arylation process, copper-mediated cyanation, copper-catalyzed arylations regioselective glycosylations. Suzuki couplings followed by arylations, X-ray absorption on rhodium-grafted hydrotalcite catalyst for heterogeneous 1,4-addition reaction of organoboron reagents to electron deficient olefins. It is used in Preparation of combretastatin analogs as potential antitumor agents and human immunodeficiency virus (HIV) protease inhibitors with antiviral activities against drug-resistant viruses
Solubility
Slightly soluble in water.
Notes
Store in cool dry conditions. Incompatible with oxidizing agents.
It is reagent used forligand-free palladium-catalyzed Suzuki-Miyaura cross-couplings, ruthenium catalyzed direct arylation of benzylic sp3 carbons of acyclic amines, Diels-Alder or C-H activation reactions, regioselective Suzuki-Miyaura coupling and tandem palladium-catalyzed intramolecular aminocarbonylation and annulations, N-arylation of phenylurea using copper acetylacetonate catalyst, environmentally benign one-pot synthesis through a double arylation process, copper-mediated cyanation, copper-catalyzed arylations regioselective glycosylations. Suzuki couplings followed by arylations, X-ray absorption on rhodium-grafted hydrotalcite catalyst for heterogeneous 1,4-addition reaction of organoboron reagents to electron deficient olefins. It is used in Preparation of combretastatin analogs as potential antitumor agents and human immunodeficiency virus (HIV) protease inhibitors with antiviral activities against drug-resistant viruses
Solubility
Slightly soluble in water.
Notes
Store in cool dry conditions. Incompatible with oxidizing agents.
RUO – Research Use Only
General References:
- Barbara J. B. Johnson. Synthesis of a nitrobenzeneboronic acid-substituted polyacrylamide and its use in purifying isoaccepting transfer ribonucleic acids. Biochemistry. 1981, 20 (21),6103-6108 .
- Alan Nadin .; José M. Sánchez López.; Andrew P. Owens.; Dean M. Howells.; Adam C. Talbot.; Timothy Harrison. New Synthesis of 1,3-Dihydro-1,4-benzodiazepin-2(2H)-ones and 3-Amino-1,3-dihydro-1,4-benzodiazepin-2(2H)-ones: Pd-Catalyzed Cross-Coupling of Imidoyl Chlorides with Organoboronic Acids.J. Org. Chem. 2003, 68 (7),2844-2852 .