4-Formylphenylboronic acid

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
4-Formylphenylboronic acid Structure
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
pka7.34±0.10(Predicted)
form Liquid
color Clear colorless to yellow-orange
PH5.5 (1g/l, H2O, 20℃)
Water Solubility Slightly Soluble in water.
Sensitive Air Sensitive
BRN 3030770
InChIKeyVXWBQOJISHAKKM-UHFFFAOYSA-N
LogP1.36 at 20℃
CAS DataBase Reference87199-17-5(CAS DataBase Reference)
EPA Substance Registry SystemBoronic 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
10
Hazard Note Irritant
TSCA T
HazardClass IRRITANT, AIR SENSITIVE
HS Code 29163990
MSDS Information
ProviderLanguage
SigmaAldrich English
ACROS English
ALFA English
4-Formylphenylboronic acid Usage And Synthesis
Chemical Propertieswhite to light yellow crystal powder
Usessuzuki reaction
Uses4-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.
Uses4-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 ExplosibilityNotclassified
4-Aminophenylboronic acid 4-Tolylboronic acid 4-Formylphenylboronic acid 3-FLUORO-2-FORMYLPHENYLBORONIC ACID 3-BROMO-2-FORMYLPHENYLBORONIC ACID Phenethylboronic acid 3-FORMYLPHENYLBORONIC ACID, PINACOL ESTER Phenylboronic acid 4-Hydroxyphenylboronic acid 2-Boronobenzaldehyde~2-Formylphenylboronic acid,2-FORMYLPHENYLBORONIC ACID 2-CHLORO-5-FORMYLPHENYLBORONIC ACID 3-Aminocarbonylphenylboronic acid 4-Carbamoylphenylboronic acid 4-FORMYLPHENYLBORONIC ACID PROPANEDIOL-1,3 CYCLIC ESTER Benzaldehyde 2,6-DIFLUORO-3-FORMYLPHENYLBORONIC ACID 5-(BENZYLOXY)-2-FORMYLPHENYLBORONIC ACID DIETHYL ACETAL 2-FLUORO-3-FORMYLPHENYLBORONIC ACID

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