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HomeProduct name list4-Formylphenylboronic acid

4-Formylphenylboronic acid

Synonym(s):p-Formylbenzeneboronic acid;p-Formylphenylboronic acid;4-(Dihydroxyboryl)benzaldehyde;4-Boronobenzaldehyde;4-Formylbenzeneboronic acid

  • CAS NO.:87199-17-5
  • Empirical Formula: C7H7BO3
  • Molecular Weight: 149.94
  • MDL number: MFCD00151823
  • EINECS: 438-670-5
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-08-19 17:35:41
4-Formylphenylboronic acid Structural

What is 4-Formylphenylboronic acid?

Chemical properties

white to light yellow crystal powder

The Uses of 4-Formylphenylboronic acid

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.

The Uses of 4-Formylphenylboronic acid

suzuki reaction

The Uses of 4-Formylphenylboronic acid

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.

What are the applications of Application

4-Formylphenylboronic acid is used for various catalytic reactions

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.]

Properties of 4-Formylphenylboronic acid

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
form  Liquid
pka 7.34±0.10(Predicted)
color  Clear colorless to yellow-orange
PH 5.5 (1g/l, H2O, 20℃)
Water Solubility  Slightly Soluble in water.
Sensitive  Air Sensitive
BRN  3030770
CAS DataBase Reference 87199-17-5(CAS DataBase Reference)
EPA Substance Registry System Boronic acid, (4-formylphenyl)- (87199-17-5)

Safety information for 4-Formylphenylboronic acid

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H317:Sensitisation, Skin
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P272:Contaminated work clothing should not be allowed out of the workplace.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352:IF ON SKIN: wash with plenty of soap and water.
P333+P313:IF SKIN irritation or rash occurs: Get medical advice/attention.

Computed Descriptors for 4-Formylphenylboronic acid

InChIKey VXWBQOJISHAKKM-UHFFFAOYSA-N

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