13505-39-0

Basic information

• Product Name: β-Hydroxybutyrophenone
• Synonyms: 1-Benzoyl-2-propanol;β-Hydroxybutyrophenone
• CAS NO: 13505-39-0
• Molecular Formula: C₁₀H₁₂O₂
• Molecular Weight: 164.2
• Mol File: 13505-39-0.mol

Chemical Properties

• Boiling Point: 150-152 °C(Press: 12 Torr)
• Appearance: /
• Density: 1.081±0.06 g/cm3(Predicted)
• PKA: 14.43±0.20(Predicted)
• CAS DataBase Reference: β-Hydroxybutyrophenone(CAS DataBase Reference)
• NIST Chemistry Reference: β-Hydroxybutyrophenone(13505-39-0)
• EPA Substance Registry System: β-Hydroxybutyrophenone(13505-39-0)

Safety Data

• Hazardous Substances Data: 13505-39-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
β-Hydroxybutyrophenone is used as an intermediate in the production of pharmaceuticals for its versatile chemical properties, contributing to the synthesis of various drug compounds.
Used in Fragrance Industry:
β-Hydroxybutyrophenone is used as a component in the creation of fragrances, leveraging its aromatic characteristics to enhance or modify scents in perfumes and other scented products.
Used in Research and Development:
β-Hydroxybutyrophenone is used as a psychotropic agent in research, where it has shown antidepressant and anxiolytic properties in some animal studies, indicating potential for further exploration in the field of mental health treatments.
Used in Asymmetric Synthesis:
β-Hydroxybutyrophenone is used as a chiral auxiliary in asymmetric synthesis, a technique crucial for producing enantiomerically pure compounds, which is essential in many areas of chemistry, including pharmaceuticals and agrochemicals.

Upstream product

• 75-07-0 acetaldehyde 
• 98-86-2 acetophenone 
• 64-17-5 ethanol 
• 39623-95-5 1-phenylprop-1-enyl acetate 
• 167780-46-3 (+/-)-2-<1-(2-hydroxypropyl)>-2-phenyl-1,3-dithiane 
• 1896-62-4 (E)-benzalacetone 
• 141277-73-8 4-chloro-3-hydroxy-1-phenyl-1-butanone 
• 70-11-1 α-bromoacetophenone 
• 93-91-4 1-phenylbutan-1,3-dione 
• 614-20-0 3-oxo-3-phenylpropionic acid 
• 71-43-2 benzene 
• 495-41-0 1-phenylbut-2-en-1-one 
• 2206-94-2 1-acetoxy-1-phenylethene 
• 100-42-5 styrene 

Downstream Products

• 34880-85-8 3-chloro-1-phenylbutan-1-one 
• 123660-24-2 (+/-)-1,1-diphenyl-1,3-butanediol 
• 93-91-4 1-phenylbutan-1,3-dione 
• 1286722-86-8 C₂₀H₁₉F₃O₄ 
• 122968-91-6 (E,3RS,1'SR)-3-(1'-hydroxy-1'phenyl-2'-butenyl)-1-methyl-2-pyrrolidinone 
• 122968-92-7 (E,3RS,1'SR)-3-(1'-hydroxy-1'-phenyl-2'-butenyl)-1-methyl-2-pyrrolidinone 
• 122969-97-5 (2'RS,3'SR)-1-(2',3'-dimethyl-1',5'-dioxo-5'-phenylpentyl)pyrrolidine 
• 122968-58-5 (2'RS,3'RS)-1-(2',3'-dimethyl-1',5'-dioxo-5'-phenylpentyl)pyrrolidine 
• 164595-89-5 (2'RS,3'RS)- and (2'RS,3'SR)-1-(2',3'-dimethyl-1',5'-dioxo-5'-phenylpentyl)pyrrolidine 
• 122969-52-2 (2'RS,3'SR)-1-(2',3'-dimethyl-5'-(hydroxyimino)-1'-oxo-5'-phenylpentyl)-pyrrolidine 
• 122969-56-6 (3RS,1'RS)-1-methyl-3-(1'-methyl-3'-phenyl-3'-((trimethylsilyl)oxy)-2'-propenyl)-2-pyrrolidinone 
• 97060-53-2 (E,2'RS,3'RS)- and (E,2'RS,3'SR)-1-(3'-hydroxy-2'-methyl-1'-oxo-3'-phenyl-4'-hexenyl)pyrrolidine 
• 122969-53-3 (3RS,1'SR)-3-(3'-(hydroxyimino)-1'-methyl-3'-phenylpropyl)-1-methyl-2-pyrrolidinone 
• 77515-94-7 N,N,3-trimethyl-5-oxo-5-phenylpentanamide 

Relevant articles and documents

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Mono-, Di-, and triaryl substituted tetrahydropyrans as cyclooxygenase-2 and tumor growth inhibitors. Synthesis and biological evaluation

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Boron-Catalyzed Dehydrative Friedel-Crafts Alkylation of Arenes Using β-Hydroxyl Ketone as MVK Precursor

Boron-catalyzed environmentally benign dehydrative Friedel-Crafts alkylation of indole/pyrrole and aniline derivatives with β-hydroxyl ketones has been developed for the first time. This method provides an efficient and green replacement of toxic and unst

Visible light-catalytic dehydrogenation of benzylic alcohols to carbonyl compounds by using an eosin y and nickel-thiolate complex dual catalyst system

We developed a simple and environmentally benign visible-light-driven dehydrogenation of benzylic alcohols to the corresponding aldehydes or ketones. By using the dual catalyst system consisting of eosin Y as a photocatalyst and a Ni(ii) complex as a proton reduction catalyst, we could dehydrogenate benzylic alcohols to aldehydes or ketones with excellent yields under mild conditions. The sole byproduct is hydrogen gas.

Indium(III)-Catalyzed Hydration and Hydroalkoxylation of α,β-Unsaturated Ketones in Aqueous Media

The hydration of α,β-unsaturated ketones with water proceeded efficiently in the presence of In(OTf)3 (20 mol%) in aqueous media to afford synthetically versatile β-hydroxyketones in moderate to good yields with good functional group compatibility. The method also can be extended to the hydroalkoxylation of α,β-unsaturated ketones with various alcohols for the efficient synthesis of β-alkoxyketones as well as tetrahydrofuran derivatives. (Figure presented.).

Chromium(III)-Catalyzed Addition of Water and Alcohol to α,β-Unsaturated Ketones for the Synthesis of β-Hydroxyl and β-Alkoxyl Ketones in Aqueous Media

An efficient chromium(III) chloride-catalyzed Michael-type reaction of water or alcohol with α,β-unsaturated ketones is developed. A variety of α,β-unsaturated ketones effectively reacted with either water or alcohols to give the corresponding β-hydroxyl ketones or β-alkoxyl ketones in modest to high yields with excellent compatibility to various functional groups. The approach was further utilized for the preparation of synthetically useful compounds containing tetrahydrofuran skeleton.

Photocatalysis with Quantum Dots and Visible Light: Selective and Efficient Oxidation of Alcohols to Carbonyl Compounds through a Radical Relay Process in Water

Selective oxidation of alcohols to aldehydes/ketones has been achieved with the help of 3-mercaptopropionic acid (MPA)-capped CdSe quantum dot (MPA-CdSe QD) and visible light. Visible-light-prompted electron-transfer reaction initiates the oxidation. The thiyl radical generated from the thiolate anion adsorbed on a CdSe QD plays a key role by abstracting the hydrogen atom from the C?H bond of the alcohol (R1CH(OH)R2). The reaction shows high efficiency, good functional group tolerance, and high site-selectivity in polyhydroxy compounds. The generality and selectivity reported here offer a new opportunity for further applications of QDs in organic transformations.

Β - hydroxy ketone compounds

The invention provides a synthesis method for a beta-hydroxy-ketone compound shown in a formula (III). The method comprises the steps that substitute vinyl acetate shown in a formula (I), a substitute alcohol compound shown in a formula (II) and an oxidizing agent are mixed to obtain reaction liquid, and the reaction liquid reacts for 2-12 hours at the temperature of 20 DEG C-120 DEG C, and then is treated to obtain the beta-hydroxy-ketone compound. The method is safe and environmentally friendly, and is a new path for synthesizing the beta-hydroxy-ketone compound containing various substituents, the substrate adaptability is good, and the reaction operation is easy.

Method for preparing organoboron compound under catalytic effect of chitosan immobilized copper and application

The invention discloses a method for preparing an organoboron compound under a catalytic effect of chitosan immobilized copper and an application. The method comprises the following steps: A) adding a chitosan immobilized copper catalyst and a ligand into a reaction tube and stirring; B) respectively continuously adding an initial raw material I and bisdiboron into a system in turn; C) stirring the whole reaction system and reacting under room temperature; D) after the reaction is ended, filtering the whole reaction system, washing with tetrahydrofuran, performing rotary evaporation and concentration on a filtrate, adopting a mixed solvent of ethyl acetate and petroleum ether at different ratios for performing column chromatography on the residues, separating and purifying, thereby acquiring a target product II. The silica gel is taken as a fixing phase for column chromatography. The invention also relates to the application of the prepared organoboron compound in compounding beta-hydroxy compound and anti-cancer drug molecules. The method is feasible; the operation is simple and convenient; the method is suitable for various substrates and can be used for successfully preparing the corresponding target compounds. The catalyst is low in dosage and is recyclable, is easily separated after the ending of the reaction, is free from metal residue and is suitable for large-scale production.

Asymmetric chemoenzymatic synthesis of 1,3-diols and 2,4-disubstituted aryloxetanes by using whole cell biocatalysts

Regio- and stereo-selective reduction of substituted 1,3-aryldiketones, investigated in the presence of different whole cell microorganisms, was found to afford β-hydroxyketones or 1,3-diols in very good yields (up to 95%) and enantiomeric excesses (up to 96%). The enantiomerically enriched aldols, obtained with the opposite stereo-preference by baker's yeast and Lactobacillus reuteri DSM 20016 bioreduction, could then be diastereoselectively transformed into optically active syn- or anti-1,3-diols by a careful choice of the chemical reducing agent (diastereomeric ratio up to 98 : 2). The latter, in turn, were stereospecifically cyclized into the corresponding oxetanes in 43-98% yields and in up to 94% ee, thereby giving a diverse selection of stereo-defined 2,4-disubstituted aryloxetanes.