4-Formylphenylboronic acid Chemical Properties

Melting point:

237-242 °C (lit.)

Boiling point:

347.6±44.0 °C(Predicted)

Density 

1.24±0.1 g/cm3(Predicted)

vapor pressure 

0Pa at 25℃

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

<10g/l

pka

7.34±0.10(Predicted)

form 

Liquid

color 

Clear colorless to yellow-orange

PH

5.5 (1g/l, H2O, 20℃)

Water Solubility 

Slightly Soluble in water.

Sensitive 

Air Sensitive

BRN 

3030770

InChIKey

VXWBQOJISHAKKM-UHFFFAOYSA-N

LogP

1.36 at 20℃

CAS DataBase Reference

87199-17-5(CAS DataBase Reference)

EPA Substance Registry System

Boronic acid, (4-formylphenyl)- (87199-17-5)

Safety Information

Hazard Codes 

C,Xi

Risk Statements 

34-36/37/38

Safety Statements 

22-26-36/37/39-45-37/39-36

RIDADR 

UN 1759 8/PG 3

WGK Germany 

3

F 

10

Hazard Note 

Irritant

TSCA 

T

HazardClass 

IRRITANT, AIR SENSITIVE

HS Code 

29163990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

4-Formylphenylboronic acid Usage And Synthesis

Chemical Properties

white to light yellow crystal powder

Uses

suzuki reaction

Uses

4-Formylbenzeneboronic acid acts as a reagent used for Palladium-catalyzed arylation Suzuki-Miyaura cross-coupling in water, copper-mediated ligandless aerobic fluoroalkylation of arylboronic acids with fluoroalkyl iodides, ligand-free copper-catalyzed coupling of nitro arenes with arylboronic acids, triethylamine-catalyzed three-component Hantzsch condensations, copper-catalyzed nitrations, oxidative mono-cleavage of dialkenes catalyzed by Trametes hirsuta, palladacycle-catalyzed cross-coupling of arylboronic acids with carboxylic anhydrides or acyl chlorides, palladium-catalyzed aerobic oxidative cross-coupling reactions. It acts as a reagent used in preparation of sensitizers with dithiafulvenyl unit as electron donor for high-efficiency dye-sensitized solar cells, a novel protein synthesis inhibitor active against Gram-positive bacteria.

Uses

4-Formylphenylboronic acid is a substrate for Suzuki cross-coupling reactions and it can be used as a reagent for:

• Palladium-catalyzed Suzuki-Miyaura cross-coupling in water.
• Copper-mediated ligandless aerobic fluoroalkylation of arylboronic acids with fluoroalkyl iodides.
• Ligand-free copper-catalyzed coupling of nitro arenes with arylboronic acids.
• Triethylamine-catalyzed three-component Hantzsch condensations.
• Copper-catalyzed nitrations.
• Oxidative mono-cleavage of dialkenes catalyzed by Trametes hirsuta.
• Palladacycle-catalyzed cross-coupling of arylboronic acids with carboxylic anhydrides or acyl chlorides.
• Palladium-catalyzed aerobic oxidative cross-coupling reactions.
• The synthesis of sensitizers with dithiafulvenyl unit as electron donor for high-efficiency dye-sensitized solar cells.
• The synthesis of a novel protein synthesis inhibitor active against Gram-positive bacteria.
• The Suzuki aryl-aryl coupling of the upper rim of hexahomotrioxacalix[3]arene.
• A rhodium-catalyzed cyclization, converting 1,5-enynes to cyclopentenes and spiro-cyclopentenes.

Flammability and Explosibility

Not classified

Synthesis

Potassium phenyltrifluoroborate (184 mg, 1.00 mmol) was added to a solution of iron trichloride (185 mg, 1.10 mmol) in 3 mL of 1:1 THF/water. The mixture was stirred at room temperature for 30 min. The reaction mixture was then passed through a short column containing neutral absorption alumina. The alumina was then washed with a mixture of ethyl acetate/hexanes (2:1) to obtain 4-Formylphenylboronic acid (105 mg, 86%). [The boronic acid products can also be isolated by simple extraction techniques.]

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