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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

Quality Level

100

Assay

95%

mp

240-244 °C (lit.)

functional group

ketone

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

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Certificates of Analysis (COA)

Lot/Batch Number
SHBP0502
22303JA
16226CA
16126CA
02821AA

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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
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)

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