4-Nitrophenylboronic acid

Synonym(s):p-nitro-benzeneboronic acid;p-Nitrophenylboronic acid;4-Nitrobenzeneboronic acid

CAS NO.：24067-17-2
Empirical Formula: C6H6BNO4
Molecular Weight: 166.93
MDL number: MFCD00161360
EINECS: 627-647-7
SAFETY DATA SHEET (SDS)
Update Date: 2023-12-25 13:23:17

What is 4-Nitrophenylboronic acid?

Description

4-Nitrobenzeneboronic acid is an arylboronic acid building block that has been used in the synthesis of phenols.

Chemical properties

White to brown powder or crystal

The Uses of 4-Nitrophenylboronic acid

4-Nitrophenylboronic Acid is a useful synthetic intermediate. It is a reagent used for ligand-free palladium-catalyzed Suzuki-Miyaura cross-couplings, Ruthenium catalyzed direct arylation of benzylic sp3 carbons of acyclic amines and Diels-Alder or C-H activation reactions.

The Uses of 4-Nitrophenylboronic acid

suzuki reaction

The Uses of 4-Nitrophenylboronic acid

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

Properties of 4-Nitrophenylboronic acid

Melting point:	285-290°C (dec.)
Boiling point:	373.7±44.0 °C(Predicted)
Density	1.40±0.1 g/cm3(Predicted)
storage temp.	Inert atmosphere,Room Temperature
solubility	DMF: 15 mg/ml; DMSO: 15 mg/ml; Ethanol: 15 mg/ml; Ethanol:PBS (pH 7.2) (1:5): 0.16 mg/ml
pka	7.04±0.10(Predicted)
form	Crystalline Powder
color	White to yellow
Water Solubility	Slightly soluble in water.
CAS DataBase Reference	24067-17-2(CAS DataBase Reference)

Safety information for 4-Nitrophenylboronic acid

Signal word	Warning
Pictogram(s)	Exclamation Mark Irritant GHS07
GHS Hazard Statements	H302:Acute toxicity,oral H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes	P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P304+P340:IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. P405:Store locked up.