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HomeProduct name list4-Chlorophenylboronic acid

4-Chlorophenylboronic acid

Synonym(s):(p-Chlorophenyl)boronic acid;4-Chlorobenzeneboronic acid;NSC 25408;p-Chlorobenzeneboronic acid

  • CAS NO.:1679-18-1
  • Empirical Formula: C6H6BClO2
  • Molecular Weight: 156.37
  • MDL number: MFCD00039137
  • EINECS: 216-845-5
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-07 13:31:19
4-Chlorophenylboronic acid Structural

What is 4-Chlorophenylboronic acid?

Chemical properties

off-white to beige crystalline powder

Chemical properties

4-Chlorophenylboronic acid is white or off-white crystalline powder. It has certain solubility in water and is soluble in strong polar organic solvents such as dimethyl sulfoxide, but insoluble in ether solvents. It has similar chemical properties to phenylboronic acid.

The Uses of 4-Chlorophenylboronic acid

4-Chlorophenylboronic acid can be used as a reactant in:

  • Palladium-catalyzed direct arylation.
  • Cyclopalladation.
  • Tandem-type Pd(II)-catalyzed oxidative Heck reaction and intramolecular C-H amidation.
  • Copper-mediated ligandless aerobic fluoroalkylation.
  • Pd-catalyzed arylative cyclization.
  • Ruthenium catalyzed direct arylation.
  • Ligand-free copper-catalyzed coupling reactions.
  • Regioselective arylation and alkynylation by Suzuki-Miyaura and Sonogashira cross-coupling reactions.

It can also be used to prepare:
  • Substituted diarylmethylidenefluorenes via Suzuki coupling reaction.
  • Baclofen lactam by Suzuki coupling of a pyrrolinyl tosylate, followed by hydrogenation reaction.
  • Palladium(II) thiocarboxamide complexes as Suzuki coupling catalysts.
  • Biaryls by Suzuki reactions of aryl chlorides, bromides, and iodides with arylboronic acids.

The Uses of 4-Chlorophenylboronic acid

4-Chlorobenzeneboronic Acid is used as a catalyst for the preparation of 4-hydroxycoumarin derivatives which display antitrypanosomal and antioxidant properties. It is also used as a catalyst for the asymmetric borane reduction of electron-deficient ketones.

What are the applications of Application

4-Chlorophenylboronic acid is a useful reagent for Suzuki couple reactions

Properties of 4-Chlorophenylboronic acid

Melting point: 284-289 °C(lit.)
Boiling point: 295.4±42.0 °C(Predicted)
Density  1.32±0.1 g/cm3(Predicted)
storage temp.  Keep in dark place,Sealed in dry,Room Temperature
solubility  DMSO
form  Crystalline Powder
pka 8.39±0.10(Predicted)
color  Off-white to beige
Water Solubility  2.5 g/100 mL
BRN  2936346
InChI InChI=1S/C6H6BClO2/c8-6-3-1-5(2-4-6)7(9)10/h1-4,9-10H
CAS DataBase Reference 1679-18-1(CAS DataBase Reference)

Safety information for 4-Chlorophenylboronic acid

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H302:Acute toxicity,oral

Computed Descriptors for 4-Chlorophenylboronic acid

InChIKey CAYQIZIAYYNFCS-UHFFFAOYSA-N
SMILES B(C1=CC=C(Cl)C=C1)(O)O

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