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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

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)

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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)
Tim Piel et al.
Toxins, 12(1) (2020-01-08)
Hydrogen peroxide (H2O2) can be used as an emergency method to selectively suppress cyanobacterial blooms in lakes and drinking water reservoirs. However, it is largely unknown how environmental parameters alter the effectiveness of H2O2 treatments. In this study, the toxic
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)
Copper-catalyzed arylation of indolin-2,3-ones with arylboronic acids
J. Zhang, et al.,
Tetrahedron, 67, 9347-9351 (2011)
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