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417548

Sigma-Aldrich

4-Chlorophenylboronic acid

95%

Sinonimo/i:

(p-Chlorophenyl)boronic acid, 4-Chlorobenzeneboronic acid, NSC 25408, p-Chlorobenzeneboronic acid

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About This Item

Formula condensata:
ClC6H4B(OH)2
Numero CAS:
Peso molecolare:
156.37
Beilstein:
2936346
Numero CE:
Numero MDL:
Codice UNSPSC:
12352103
ID PubChem:
NACRES:
NA.22

Livello qualitativo

Saggio

95%

Punto di fusione

284-289 °C (lit.)

Gruppo funzionale

chloro

Stringa SMILE

OB(O)c1ccc(Cl)cc1

InChI

1S/C6H6BClO2/c8-6-3-1-5(2-4-6)7(9)10/h1-4,9-10H
CAYQIZIAYYNFCS-UHFFFAOYSA-N

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Applicazioni

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.

Altre note

Contains a varying amounts of anhydride

Pittogrammi

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Avvertenze

Warning

Indicazioni di pericolo

Consigli di prudenza

Classi di pericolo

Acute Tox. 4 Oral

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Dispositivi di protezione individuale

dust mask type N95 (US), Eyeshields, Gloves


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Tetrahedron Letters, 48, 827-827 (2007)
Seul Gi Kim et al.
International journal of molecular sciences, 20(21) (2019-10-31)
Herein, we describe the fabrication and characterization of carbonized disulfide core-crosslinked polymer dots with pH-cleavable colorimetric nanosensors, based on diol dye-conjugated fluorescent polymer dots (L-PD), for reduction-triggered paclitaxel (PTX) release during fluorescence imaging-guided chemotherapy of tumors. L-PD were loaded with
A Double Suzuki Approach for Synthesis of Substituted Diarylmethylidenefluorenes
C. V. Ramana, et al.
Synlett, 1, 127-128 (2007)
Immobilized palladium on surface-modified Fe3O4/SiO2 nanoparticles: as a magnetically separable and stable recyclable high-performance catalyst for Suzuki and Heck cross-coupling reactions
Du, Q.; et al.
Tetrahedron, 68, 3577-3584 (2012)
Copper-Mediated Aerobic Fluoroalkylation of Arylboronic Acids with Fluoroalkyl Iodides at Room Temperature
Qi, Q.; Shen, Q.; Lu, L.
Journal of the American Chemical Society, 134, 648-6551 (2012)

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