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4-Formylphenylboronic acid

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4-Formylphenylboronic acid Basic information

Product Name:
4-Formylphenylboronic acid
Synonyms:
  • RARECHEM AH PB 0193
  • TIMTEC-BB SBB004077
  • P-FORMYLPHENYLBORONIC ACID
  • AKOS BRN-0111
  • 4-FORMYLBENZENEBORONIC ACID
  • 4-FORMYLPHENYLBORONIC ACID
  • 4-BORONOBENZALDEHYDE
  • 4-(Dihydroxyboryl)benzaldehyde, 4-Boronobenzaldehyde
CAS:
87199-17-5
MF:
C7H7BO3
MW:
149.94
EINECS:
438-670-5
Product Categories:
  • Substituted Boronic Acids
  • Boron, Nitrile, Thio,& TM-Cpds
  • ALDEHYDE
  • Aldehydes
  • blocks
  • Carbonyl Compounds
  • BoronicAcids
  • Boronic Acid series
  • Boronic Acid
  • Aryl
  • Organoborons
  • B (Classes of Boron Compounds)
  • CHIRAL CHEMICALS
  • Boronic Acids & Esters
  • pharmacetical
  • Boronic Acids & Esters
  • Phenyls & Phenyl-Het
  • Boronic acids
  • Phenyls & Phenyl-Het
  • Boronate Ester
  • Potassium Trifluoroborate
  • 87199-17-5
Mol File:
87199-17-5.mol
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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
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
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)
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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
10
Hazard Note 
Irritant
TSCA 
T
HazardClass 
IRRITANT, AIR SENSITIVE
HS Code 
29163990

MSDS

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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.]

4-Formylphenylboronic acid Preparation Products And Raw materials

Preparation Products

Raw materials

4-Formylphenylboronic acidSupplier

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