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470813

Sigma-Aldrich

3-Acetylphenylboronic acid

≥95%

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About This Item

Linear Formula:
CH3COC6H4B(OH)2
CAS Number:
204841-19-0
Molecular Weight:
163.97
MDL number:
MFCD01074678
UNSPSC Code:
12352103
PubChem Substance ID:
24870685
NACRES:
NA.22

assay

≥95%

impurities

<10% 3-acetylphenylboronic anhydride

mp

204-208 °C (lit.)

SMILES string

CC(=O)c1cccc(c1)B(O)O

InChI

1S/C8H9BO3/c1-6(10)7-3-2-4-8(5-7)9(11)12/h2-5,11-12H,1H3

InChI key

SJGGDZCTGBKBCK-UHFFFAOYSA-N

Application

3-Acetylphenylboronic acid can be used as a substrate:
  • In the synthesis of symmetric biaryls via oxidative dimerization using a palladium catalyst and water as a solvent.
  • In the synthesis of aryl fluorides through electrophilic fluorination reaction using acetyl hypofluorite.
  • In the coupling reactions of organoboranes with olefins using molecular oxygen and palladium catalyst.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Oxygen-promoted Pd (II) catalysis for the coupling of organoboron compounds and olefins
Jung YC, et al.
Organic Letters, 5(13), 2231-2234 (2003)
Fluorination of aryl boronic acids using acetyl hypofluorite made directly from diluted fluorine
Vints I, et al.
The Journal of Organic Chemistry, 78(23), 11794-11797 (2013)
Oxidative dimerization: Pd (II) catalysis in the presence of oxygen using aqueous media
Parrish JP, et al.
Tetrahedron Letters, 43(44), 7899-7902 (2002)

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