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: 2024-09-09 19:09:56
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) |
 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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