149104-90-5

Basic information

• Product Name: 4-Acetylphenylboronic acid
• Synonyms: RARECHEM AH PB 0162;P-ACETYLPHENYLBORONIC ACID;TIMTEC-BB SBB000146;4-ACETYLPHENYLBORONIC ACID;4-ACETYLBENZENEBORONIC ACID;ACETOPHENONE-4-BORONIC ACID;AKOS BRN-0001;4-Acetylphenylboronic acid~4-Boronoacetophenone
• CAS NO: 149104-90-5
• Molecular Formula: C₈H₉BO₃
• Molecular Weight: 163.97
• EINECS: -0
• Product Categories: ACETYLGROUP;blocks;BoronicAcids;Boronic Acid series;Boronic Acid;Acetyl;Aryl;Organoborons;B (Classes of Boron Compounds);Boronic Acids;Boronic Acids;Boronic Acids and Derivatives;Boronate Ester;Potassium Trifluoroborate
• Mol File: 149104-90-5.mol
• Article Data: 18

Chemical Properties

• Melting Point: 240-244 °C(lit.)
• Boiling Point: 354.2 °C at 760 mmHg
• Flash Point: 168 °C
• Appearance: Pale yellow to yellow/Crystalline Powder
• Density: 1.19 g/cm³
• Vapor Pressure: 1.25E-05mmHg at 25°C
• Refractive Index: 1.535
• Storage Temp.: Keep Cold
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 7.58±0.10(Predicted)
• Water Solubility: 25 g/L
• BRN: 7869162
• CAS DataBase Reference: 4-Acetylphenylboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Acetylphenylboronic acid(149104-90-5)
• EPA Substance Registry System: 4-Acetylphenylboronic acid(149104-90-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 149104-90-5(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powder

Uses

Different sources of media describe the Uses of 149104-90-5 differently. You can refer to the following data:
1. suzuki reaction
2. Reactant involved in:Palladium-catalyzed decarboxylative couplingCopper-catalyzed hydroxylationPalladium-catalyzed Suzuki-Miyaura cross-couplingCross-coupling with α-bromocarbonyl compoundsOxidation catalyzed by Baeyer-Villiger monooxygenases1,5-substitution reactions
3. 4-Acetylphenylboronic acid4-Acetylphenylboronic Acid is used in several metal catalyzed cross-coupling reaction studies.

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.

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

Upstream product

• 518336-20-4 (4-(1-hydroxyethyl)phenyl)boronic acid 
• 13675-18-8 tetrahydroxydiboron 
• 99-90-1 para-bromoacetophenone 
• 109613-00-5 4-acetophenyl triflate 
• 2156-04-9 4-Vinylphenylboronic acid 
• 13329-40-3 4-Iodoacetophenone 
• 99-92-3 p-aminobenzophenone 
• 350-47-0 1-(4-acetylphenyl)diazonium tetrafluoroborate 
• 61390-40-7 1-bromo-4-(1,1-diethoxyethyl)benzene 
• 1173922-30-9 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethanol 
• 171364-81-1 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethanone 

Downstream Products

• 13021-18-6 1-(4'-methoxy-biphenyl-4-yl)-ethanone 
• 94705-09-6 (4-acetylphenyl)(phenyl)methanol 
• 215876-83-8 2-(4-acetylphenyl)-4,5-dimethyl-1,3,2-dioxaborolane 
• 99-93-4 4-Hydroxyacetophenone 
• 173464-57-8 (E)-3-(4-acetylphenyl)acrylic acid butyl ester 
• 53689-84-2 4-acetylbenzophenone 
• 23600-83-1 1-(4-(phenylamino)phenyl)ethanone 
• 20488-43-1 4-acetyl-trans-stilbene 
• 171364-81-1 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethanone 
• 402822-63-3 2-diphenylphosphinyl-4'-acetylbiphenyl 
• 460088-33-9 1-(4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl)ethan-1-one 

Relevant articles and documents

Transition-Metal-Free Borylation of Aryl Bromide Using a Simple Diboron Source

In this study, we developed a simple transition-metal-free borylation reaction of aryl bromides. Bis-boronic acid (BBA), was used, and the borylation reaction was performed using a simple procedure at a mild temperature. Under mild conditions, aryl bromides were converted to arylboronic acids directly without any deprotection steps and purified by conversion to trifluoroborate salts. The functional group tolerance was considerably high. The mechanism study suggested that this borylation reaction proceeds via a radical pathway.

Bedford-type palladacycle-catalyzed miyaura borylation of aryl halides with tetrahydroxydiboron in water

A mild aqueous protocol for palladium catalyzed Miyaura borylation of aryl iodides, aryl bromides and aryl chlorides with tetrahydroxydiboron (BBA) as a borylating agent is developed. The developed methodology requires low catalyst loading of Bedford-type palladacycle catalyst (0.05 mol %) and works best under mild reaction conditions at 40 °C in short time of 6 h in water. In addition, our studies show that for Miyaura borylation using BBA in aqueous condition, maintaining a neutral reaction pH is very important for reproducibility and higher yields of corresponding borylated products. Moreover, our protocol is applicable for a broad range of aryl halides, corresponding borylated products are obtained in excellent yields up to 93% with 29 examples demonstrating its broad utility and functional group tolerance.

Wacker-Type Oxidation Using an Iron Catalyst and Ambient Air: Application to Late-Stage Oxidation of Complex Molecules

A practical and general iron-catalyzed Wacker-type oxidation of olefins to ketones is presented, and it uses ambient air as the sole oxidant. The mild oxidation conditions enable exceptional functional-group tolerance, which has not been demonstrated for any other Wacker-type reaction to date. The inexpensive and nontoxic reagents [iron(II) chloride, polymethylhydrosiloxane, and air] can, therefore, also be employed to oxidize complex natural-product-derived and polyfunctionalized molecules.