4-Nitrophenylboronic acid Chemical Properties

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.

InChI

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

InChIKey

NSFJAFZHYOAMHL-UHFFFAOYSA-N

SMILES

B(C1=CC=C([N+]([O-])=O)C=C1)(O)O

CAS DataBase Reference

24067-17-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

Safety Statements 

26-36/37/39-24/25

WGK Germany 

3

Hazard Note 

Harmful

HS Code 

29319090

4-Nitrophenylboronic acid Usage And Synthesis

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

Uses

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.

Uses

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

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

Uses

suzuki reaction

Synthesis

GENERAL METHOD: To a solution of 4-nitroaniline (0.5 mmol, 1.0 eq.) in methanol (1.0 mL) was added hydrochloric acid (0.5 mL, 1.5 mmol, 3.0 eq.) followed by water (0.5 mL). The reaction mixture was stirred for 2 minutes and then sodium nitrite solution (0.25 mL) was added. Sodium nitrite solution was prepared by dissolving 35 mg of sodium nitrite in water (0.25 mL). The mixture was stirred at 0-5 °C for 30 min, followed by the addition of hydrochloric acid (135 mg, 1.5 mmol, 3.0 equiv) in methanol (1.0 mL). Stirring of the reaction mixture was continued for 60 min. Upon completion of the reaction, it was diluted with the addition of water (10 mL) and extracted with dichloromethane (50 mL, 3 times). The organic layers were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 4-nitrophenylboronic acid.

References

[1] Synlett, 2014, vol. 25, # 11, p. 1577 - 1584
[2] Chemistry - A European Journal, 2014, vol. 20, # 22, p. 6608 - 6612

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