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673854

Sigma-Aldrich

4-Nitrophenylboronic acid

≥95.0%

Synonym(s):

4-Nitrobenzeneboronic acid, p-Nitrophenylboronic acid, p-nitro-benzeneboronic acid

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About This Item

Linear Formula:
(O2N)C6H4(B(OH)2)
CAS Number:
24067-17-2
Molecular Weight:
166.93
MDL number:
MFCD00161360
UNSPSC Code:
12352103
PubChem Substance ID:
24885181
NACRES:
NA.22

Quality Level

100

Assay

≥95.0%

form

solid

mp

285-290 °C (dec.)

SMILES string

OB(O)c1ccc(cc1)[N+]([O-])=O

InChI

1S/C6H6BNO4/c9-7(10)5-1-3-6(4-2-5)8(11)12/h1-4,9-10H

InChI key

NSFJAFZHYOAMHL-UHFFFAOYSA-N

Application

Reagent used for
  • Ligand-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 cyanations
  • 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

Reagent used in Preparation of
  • Combretastatin analogs as potential antitumor agents
  • Human immunodeficiency virus (HIV) protease inhibitors with antiviral activities against drug-resistant viruses

Other Notes

May contain varying amounts of anhydride

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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David A Degoey et al.
Journal of medicinal chemistry, 54(20), 7094-7104 (2011-09-09)
Because there is currently no cure for HIV infection, patients must remain on long-term drug therapy, leading to concerns over potential drug side effects and the emergence of drug resistance. For this reason, new and safe antiretroviral agents with improved
Tetrahedron, 63, 6131-6131 (2007)
Abdallah Hamze et al.
ChemMedChem, 6(12), 2179-2191 (2011-10-13)
A novel class of isocombretastatin A-4 (isoCA-4) analogues with modifications at the 3'-position of the B-ring by replacement with C-linked substituents was studied. Exploration of the structure-activity relationships of theses analogues led to the identification of several compounds that exhibit
Copper-catalyzed arylation of indolin-2,3-ones with arylboronic acids
J. Zhang, et al.,
Tetrahedron, 67, 9347-9351 (2011)
Rhodium-grafted hydrotalcite catalyst for heterogeneous 1,4-addition reaction of organoboron reagents to electron deficient olefins
Motokura, K.; et al.
Green Chemistry, 13, 2416-2422 (2011)
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