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470821

Sigma-Aldrich

4-Acetylphenylboronic acid

95%

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About This Item

Linear Formula:
CH3COC6H4B(OH)2
CAS Number:
149104-90-5
Molecular Weight:
163.97
MDL number:
MFCD01074667
UNSPSC Code:
12352103
PubChem Substance ID:
24870686
NACRES:
NA.22

Assay

95%

mp

240-244 °C (lit.)

SMILES string

CC(=O)c1ccc(cc1)B(O)O

InChI

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

InChI key

OBQRODBYVNIZJU-UHFFFAOYSA-N

General description

4-Acetylphenylboronic acid is a boronate, belongs to a class of synthetic organic compounds. It reacts rapidly with peroxynitrite (ONOO(-)) to form stable hydroxy derivatives. It undergoes Suzuki coupling with 4-bromotriphenylamine catalyzed by dichlorobis(triphenylphosphine)Pd(II), during the synthesis of dendrimers.

Application

4-Acetylphenylboronic acid was used in the synthesis of 4′-azidoacetophenone.
Reactant involved in:
  • Palladium-catalyzed decarboxylative coupling
  • Copper-catalyzed hydroxylation
  • Palladium-catalyzed Suzuki-Miyaura cross-coupling
  • Cross-coupling with α-bromocarbonyl compounds
  • Oxidation catalyzed by Baeyer-Villiger monooxygenases
  • 1,5-substitution reactions

Other Notes

Contains varying amounts of anhydride

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Adam Sikora et al.
Free radical biology & medicine, 47(10), 1401-1407 (2009-08-19)
In this study, we show that boronates, a class of synthetic organic compounds, react rapidly and stoichiometrically with peroxynitrite (ONOO(-)) to form stable hydroxy derivatives as major products. Using a stopped-flow kinetic technique, we measured the second-order rate constants for
A New Efficient Convergent Synthesis of Conjugated Aryl-containing Dendrimers.
El-Deeb IM and Lee SH.
Bull. Korean Chem. Soc., 31(6), 1757-1760 (2010)
Kimberly D Grimes et al.
Synthesis, 2010(9), 1441-1448 (2010-06-08)
We report the copper(II)-catalyzed conversion of organoboron compounds into the corresponding azide derivatives. A systematic series of phenylboronic acid derivatives is evaluated to examine the importance of steric and electronic effects of the substituents on reaction yield as well as

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