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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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCP9396
MKCL6346
MKCJ4905
MKCD6576
MKCC0577

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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)
An efficient copper-catalyzed one-pot synthesis of diaryl thioethers by coupling of arylboronic acids with potassium ethyl xanthogenate under mild conditions
Wang, L.; et al.
Synlett, 20, 3041-3045 (2011)
An efficient access to 2,3-diarylimidazo[1,2-a]pyridines via imidazo[1,2-a]pyridin-2-yl triflate through a Suzuki cross-coupling reaction-direct arylation sequence
Marhadour, S.; et al.
Tetrahedron Letters, 53, 297-300 (2012)
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
Tetrahedron, 63, 6131-6131 (2007)
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